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Journal articles on the topic 'Aziridines'

Author: Grafiati

Published: 4 June 2021

Last updated: 30 November 2024

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1

D’hooghe, Matthias, Hyun-Joon Ha, and Lingamurthy Macha. "Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives." Synthesis 51, no. 07 (February 18, 2019): 1491–515. http://dx.doi.org/10.1055/s-0037-1611715.

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Various (activated and non-activated) aziridines with diverse substitution patterns have been deployed successfully as starting materials for the synthesis of a wide variety of alkaloids via suitable functionalization and aziridine ring transformation. Alternatively, the preparation and interception of reactive aziridine intermediates has also been shown to constitute a valid approach toward alkaloid synthesis. This review summarizes aziridine-mediated syntheses of alkaloids, in which the aziridine is mobilized as either a substrate or an advanced synthetic intermediate.1 Introduction2 Alkaloids Synthesis from Aziridine Starting Materials2.1 (2R)- and (2S)-Hydroxymethyl-N-(1-phenylethyl)aziridines2.2 N-Benzylaziridine-2-carboxylates2.3 2-Substituted N-Tosyl- or N-Tritylaziridines2.4 2,3-Disubstituted N-Cbz- or N-Tosylaziridines2.5 N-DMB-aziridines3 Alkaloids Synthesis from Aziridines as Key Advanced Synthetic Intermediates3.1 Alkylative Aziridine Ring Opening3.2 Arylative Aziridine Ring Opening3.3 Ring Expansion3.4 Oxidative Aziridine Ring Opening3.5 Heteroatomic Nucleophilic Aziridine Ring Opening3.6 Reductive Aziridine Ring Opening4 Conclusion

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2

Strumfs, Boriss, Romans Uljanovs, Kirils Velikijs, Peteris Trapencieris, and Ilze Strumfa. "3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches." International Journal of Molecular Sciences 22, no. 18 (September 13, 2021): 9861. http://dx.doi.org/10.3390/ijms22189861.

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Aziridination reactions represent a powerful tool in aziridine synthesis. Significant progress has been achieved in this field in the last decades, whereas highly functionalized aziridines including 3-arylated aziridine-2-carbonyl compounds play an important role in both medical and synthetic chemistry. For the reasons listed, in the current review we have focused on the ways to obtain 3-arylated aziridines and on the recent advances (mainly since the year 2000) in the methodology of the synthesis of these compounds via aziridination.

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3

Chai, Zhuo. "Catalytic Asymmetric Transformations of Racemic Aziridines." Synthesis 52, no. 12 (March 16, 2020): 1738–50. http://dx.doi.org/10.1055/s-0039-1690857.

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The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.1 Introduction2 Reaction of Racemic 2-Vinylaziridines3 Reaction of Racemic 2-Alkylaziridines3.1 Regiodivergent Parallel Kinetic Resolution3.2 Kinetic Resolution4 Reaction of Racemic 2-(Hetero)arylaziridines4.1 Kinetic Resolution4.2 Enantioconvergent Transformation5 Reaction of Racemic Donor–Acceptor-Type Aziridines6 Conclusion and Outlook

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4

Bera, Partha Sarathi, Yafia Kousin Mirza, Tarunika Sachdeva, and Milan Bera. "Recent Advances in Transition Metal-Catalyzed Ring-Opening Reaction of Aziridine." Compounds 4, no. 4 (October 11, 2024): 626–49. http://dx.doi.org/10.3390/compounds4040038.

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The smallest strained, saturated N-heterocycles, such as aziridine, can be a valuable building block in synthetic organic chemistry. Ring-opening reactions with various nucleophiles could be the most important strategy to synthesize various value-added molecular entities. Therefore, regioselective ring-opening reactions of aziridines with various heteroatomic nucleophiles and carbon nucleophiles establish a useful synthetic methodology to synthesize biologically relevant β-functionalized alkylamines. The regio-selective ring-opening of aziridines is highly dependent on the substrate combination, and stereochemical control is challenging for Lewis acid-promoted reactions. Therefore, the development of a robust, catalytic ring-opening process that assists in the accurate prediction of regioselectivity and stereochemistry is highly desirable. Consequently, a large number of publications detailing distinct methods for aziridine ring-opening reactions can be found in the literature. In this review, we discuss several transition metal catalyzed cross-coupling reaction protocols for the ring opening of substituted aziridines with various carbon nucleophiles.

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5

Bauermeister, Slegelinde, Agnes M. Modro, Tom A. Modro, and Andrzej Zwierzak. "Phosphoric amides. Part 11. Intramolecular reactivity of phosphorotriamidates." Canadian Journal of Chemistry 69, no. 5 (May 1, 1991): 811–16. http://dx.doi.org/10.1139/v91-120.

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Five N-(2-chloroethyl)phosphorotriamidates, (RNH)2P(O)NHCH2CH2Cl, have been synthesized, and their behavior under strongly basic conditions was studied. For N-alkyl derivatives (R = Me, PhCH2), base-promoted intramolecular displacement of chloride yielded the N-phosphorylated aziridine, (RNH)2P(O)NC2H4, as the exclusive cyclization product. For N-aryl derivatives (R = Ar), both the aziridine and the 1,3,2-diazaphospholidine, [Formula: see text], products could be obtained in comparable yields. The N-aromatic cyclic products are mutually interconvertible: 1,3,2-diazaphospholidines rearrange to the corresponding aziridines upon treatment with base, while bromide ions catalyze the reverse isomerization. Key words: phosphoramidates acidity, N-phosphorylated aziridines – 1,3,2-diazaphospholidines isomerization, 1,3 vs. 1,5 cyclization.

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6

Klarek, Mateusz, Tomasz Siodła, Tahar Ayad, David Virieux, and Magdalena Rapp. "Access to 2-Fluorinated Aziridine-2-phosphonates from α,α-Halofluorinated β-Iminophosphonates—Spectroscopic and Theoretical Studies." Molecules 28, no. 14 (July 22, 2023): 5579. http://dx.doi.org/10.3390/molecules28145579.

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The efficient one-pot halofluorination of a β-enaminophosphonate/β-iminophosphonate tautomeric mixture resulting in α,α-halofluorinated β-iminophosphonates is reported. Subsequent imine reduction gave the corresponding β-aminophosphonates as a racemic mixture or with high diastereoselectivity. The proposed protocol is the first example of a synthesis of N-inactivated aziridines substituted by a fluorine and phosphonate moiety on the same carbon atom. Based on spectroscopic and theoretical studies, we determined the cis/trans geometry of the resulting fluorinated aziridine-2-phosphonate. Our procedure, involving the reduction of cis/trans-fluoroaziridine mixture 24, allows us to isolate chiral trans-aziridines 24 as well as cis-aziridines 27 that do not contain a fluorine atom. We also investigated the influence of the fluorine atom on the reactivity of aziridine through an acid-catalyzed regioselective ring-opening reaction. The results of DFT calculations, at the PCM/ωB97x-D/def2-TZVPD level of theory, are in good agreement with the experiments. The transition states of the SN2 intramolecular cyclization of vicinal haloamines have been modeled.

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7

Jat, Jawahar L., Mahesh P. Paudyal, Hongyin Gao, Qing-Long Xu, Muhammed Yousufuddin, Deepa Devarajan, Daniel H. Ess, László Kürti, and John R. Falck. "Direct Stereospecific Synthesis of Unprotected N-H and N-Me Aziridines from Olefins." Science 343, no. 6166 (January 2, 2014): 61–65. http://dx.doi.org/10.1126/science.1245727.

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Despite the prevalence of the N-H aziridine motif in bioactive natural products and the clear advantages of this unprotected parent structure over N-protected derivatives as a synthetic building block, no practical methods have emerged for direct synthesis of this compound class from unfunctionalized olefins. Here, we present a mild, versatile method for the direct stereospecific conversion of structurally diverse mono-, di-, tri-, and tetrasubstituted olefins to N-H aziridines usingO-(2,4-dinitrophenyl)hydroxylamine (DPH) via homogeneous rhodium catalysis with no external oxidants. This method is operationally simple (i.e., one-pot), scalable, and fast at ambient temperature, furnishing N-H aziridines in good-to-excellent yields. Likewise, N-alkyl aziridines are prepared from N-alkylated DPH derivatives. Quantum-mechanical calculations suggest a plausible Rh-nitrene pathway.

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8

Okoromoba, Otome E., Zhou Li, Nicole Robertson, Mark S. Mashuta, Uenifer R. Couto, Cláudio F. Tormena, Bo Xu, and Gerald B. Hammond. "Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions." Chemical Communications 52, no. 91 (2016): 13353–56. http://dx.doi.org/10.1039/c6cc07855a.

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DMPU–HF demonstrates good reactivity and regioselectivity in conversion of aziridines into biologically important β-fluoroamines. The stereochemistry of aziridine-opening was found to be depend greatly on substitution pattern.

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9

Cheviet, Thomas, Ilyana Gonzales, and Suzanne Peyrottes. "Synthesis of N-methylene phosphonate aziridines: reaction scope and mechanistic insights." New Journal of Chemistry 46, no. 14 (2022): 6453–60. http://dx.doi.org/10.1039/d2nj00595f.

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Treatment of N-carbamoyl aziridines by the diethyl phosphite anion affords either α-methylene-phosphonate or gem-bisphosphonate derivatives containing an aziridine motif depending on the nature of the base used.

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10

Giri, Chandan, Jen-Yu Chang, Pierre Canisius Mbarushimana, and Paul A. Rupar. "The Anionic Polymerization of a tert-Butyl-Carboxylate-Activated Aziridine." Polymers 14, no. 16 (August 10, 2022): 3253. http://dx.doi.org/10.3390/polym14163253.

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N-Sulfonyl-activated aziridines are known to undergo anionic-ring-opening polymerizations (AROP) to form polysulfonyllaziridines. However, the post-polymerization deprotection of the sulfonyl groups from polysulfonyllaziridines remains challenging. In this report, the polymerization of tert-butyl aziridine-1-carboxylate (BocAz) is reported. BocAz has an electron-withdrawing tert-butyloxycarbonyl (BOC) group on the aziridine nitrogen. The BOC group activates the aziridine for AROP and allows the synthesis of low-molecular-weight poly(BocAz) chains. A 13C NMR spectroscopic analysis of poly(BocAz) suggested that the polymer is linear. The attainable molecular weight of poly(BocAz) is limited by the poor solubility of poly(BocAz) in AROP-compatible solvents. The deprotection of poly(BocAz) using trifluoroacetic acid (TFA) cleanly produces linear polyethyleneimine. Overall, these results suggest that carbonyl groups, such as BOC, can play a larger role in the in the activation of aziridines in anionic polymerization and in the synthesis of polyimines.

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11

Lei, Jie, Gui-Ting Song, Liu-Jun He, Ya-Fei Luo, Dian-Yong Tang, Hui-Kuan Lin, Brendan Frett, Hong-yu Li, Zhong-Zhu Chen, and Zhi-Gang Xu. "One-pot construction of functionalized aziridines and maleimides via a novel pseudo-Knoevenagel cascade reaction." Chemical Communications 56, no. 14 (2020): 2194–97. http://dx.doi.org/10.1039/c9cc08220d.

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12

Wosińska-Hrydczuk, Marzena, Przemysław J. Boratyński, and Jacek Skarżewski. "Regioselective and Stereodivergent Synthesis of Enantiomerically Pure Vic-Diamines from Chiral β-Amino Alcohols with 2-Pyridyl and 6-(2,2′-Bipyridyl) Moieties." Molecules 25, no. 3 (February 7, 2020): 727. http://dx.doi.org/10.3390/molecules25030727.

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In this report, we describe the synthetic elaboration of the easily available enantiomerically pure β-amino alcohols. Attempted direct substitution of the hydroxyl group by azido-functionality in the Mitsunobu reaction with hydrazoic acid was inefficient or led to a diastereomeric mixture. These outcomes resulted from the participation of aziridines. Intentionally performed internal Mitsunobu reaction of β-amino alcohols gave eight chiral aziridines in 45–82% yield. The structural and configuration identity of products was confirmed by NMR data compared to the DFT calculated GIAO values. For 1,2,3-trisubstituted aziridines slow configurational inversion at the endocyclic nitrogen atom was observed by NMR at room temperature. Moreover, when aziridine was titrated with Zn(OAc)2 under NMR control, only one of two N-epimers directly participated in complexation. The aziridines underwent ring opening with HN3 to form the corresponding azido amines as single regio- and diastereomers in 90–97% yield. Different results were obtained for 1,2-disubstituted and 1,2,3-trisubstituted aziridines. For the later aziridines ring closure and ring opening occurred at different carbon stereocenters, thus yielding products with two inverted configurations, compared to the starting amino alcohol. The 1,2-disubstituted aziridines produced azido amines of the same configuration as the starting β-amino alcohols. To obtain a complete series of diastereomeric vic-diamines, we converted the amino alcohols into cyclic sulfamidates, which reacted with sodium azide in SN2 reaction (25–58% overall yield). The azides obtained either way underwent the Staudinger reduction, giving a series of six new chiral vic-diamines of defined stereochemistries.

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13

Yoon, Hyo Jae, Sangmin Jung, and Seo Yeon Kim. "Force-Induced Cycloaddition of Aziridine: Can We Force a New Route?" Synlett 31, no. 14 (June 18, 2020): 1343–48. http://dx.doi.org/10.1055/s-0040-1707145.

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Cycloaddition reactions of aziridines with dipolarophiles under traditional thermal or photochemical conditions entail destructive routes to form reactive intermediates such as an azomethine ylide. This article highlights a recent study that demonstrates a cycloaddition reaction of aziridine induced by mechanical force. Experimental results suggest that the force-induced cycloaddition of aziridine with dimethyl acetylenedicarboxylate as a dipolarophile does not seem to involve an ylide, with implications for a possible new reaction route.1 Rivalry between Aziridine and Epoxide2 Mechanochemically Responsive Polymers3 Aziridine Mechanophore4 Concluding Remarks and Outlook

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14

Sun, Shan, Ilaria Tirotta, Nicholas Zia, and Craig A. Hutton. "Selective Cleavage of Carbamate Protecting Groups from Aziridines with Otera's Catalyst." Australian Journal of Chemistry 67, no. 3 (2014): 411. http://dx.doi.org/10.1071/ch13464.

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Otera’s distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selectivity is due to the longer, weaker N–C bond of aziridinyl carbamates, as inferred through IR and crystallographic analyses.

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15

Rosillo, Félix, Yosslen Aray, Jesús Rodríguez, and Juan Murgich. "The topology of the valence shell and the electric field gradient at the nitrogen nucleus in aziridines." Canadian Journal of Chemistry 74, no. 6 (June 1, 1996): 1116–20. http://dx.doi.org/10.1139/v96-125.

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The ab initio molecular charge density ρ(r) of substituted aziridines was calculated at the MP2 level for R = -H, -CH3, -CF3, -Cl, -NO2, -CN, -OH, -NO, and -F. The use of the topology of the Laplacian of ρ(r) allowed the analysis of the electric field gradient (EFG) at the nitrogen nucleus directly in terms of its valence shell charge concentration. The EFG changed sign and the orientation of its y- and z-axes with respect to aziridine when R = -Cl, -NO2, -CN, -OH, -NO, and -F. The changes in the EFG in these aziridines upon substitution were correlated with those calculated in the valence charge concentrations along the direction of the N—R bond. The sign of the qzz component and the orientation of the principal axes of the EFG tensor were found to be determined by the relative value of the contributions from the charge concentrations at the points in the valence shell along the N—C and N—R bond directions. Key words: molecular charge distribution, aziridines, Laplacian of the charge density, electric field gradient.

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16

Buchcic, Aleksandra, Anna Zawisza, Stanisław Leśniak, Justyna Adamczyk, Adam Marek Pieczonka, and Michał Rachwalski. "Enantioselective Mannich Reaction Promoted by Chiral Phosphinoyl-Aziridines." Catalysts 9, no. 10 (October 10, 2019): 837. http://dx.doi.org/10.3390/catal9100837.

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In this study, a set of enantiomerically pure aziridines bearing a phosphine oxide moiety were prepared in high yields and tested as chiral catalysts in the direct asymmetric Mannich reaction of hydroxyacetone, an amine (p-anisidine), and various aromatic aldehydes. The appropriate Mannich adducts were formed in chemical yields from moderate to good with a high level of enantio- and diastereoselectivity. The best results were obtained using the catalysts bearing a free NH-aziridine subunit.

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17

Karban, Jindřich, Miloš Buděšínský, and Jiří Kroutil. "Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra." Collection of Czechoslovak Chemical Communications 69, no. 10 (2004): 1939–54. http://dx.doi.org/10.1135/cccc20041939.

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A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminium hydride reduction of vicinal trans azido tosylates. Unusual formation of the aziridine ring from precursors with the trans-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra of the aziridines are discussed.

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18

Monteiro, Júlia L., Natália M. Moreira, Deborah A. dos Santos, Márcio W. Paixão, and Arlene G. Corrêa. "Step economy strategy for the synthesis of amphoteric aminoaldehydes, key intermediates for reduced hydantoins." Pure and Applied Chemistry 90, no. 1 (January 26, 2018): 121–32. http://dx.doi.org/10.1515/pac-2017-0705.

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AbstractDespite of the orthogonal reactivity of the N–H aziridines aldehyde, these compounds exist as an equilibrium of three different forms – whereas the dimeric one is mostly observed in a variety of solvents. In this work, we have developed an alternative protocol for the aminoaldehyde dimers synthesis in two steps starting with an organocatalyzed aziridination between α,β-unsaturated aldehydes and a protected amine to afford known isolable and stable N-protected aziridine aldehydes. After Boc-deprotection, dimeric species were immediately formed from monomeric N–H aziridine aldehydes. From this building-block new reduced hydantoins were prepared via [3+2]-annulation with isocyanates.

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19

Rauf, Abdul, and Shabana Ahmad. "Aziridination of Methyl Long-chain Alkenoates Using Chloramine-T." Journal of Chemical Research 2005, no. 6 (June 2005): 407–9. http://dx.doi.org/10.3184/0308234054506802.

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Methyl long-chain alkenoates on treatment with chloramine-T [N-chloro-N-sodio-p-toluenesulfonamide] resulted in the formation of the corresponding aziridines in moderate yields. The N-substituted aziridine derivatives based on methyl undec-10-enoate (1), methyl (Z)-octadec-9-enoate (3) and methyl (9Z,12R)-12-hydroxyoctadec-9-enoate (5) have been synthesised under mild reaction conditions. The products were characterised using micro-analytical and spectral data.

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20

Huck, Lena, Juan F. González, Elena de la Cuesta, and J. Carlos Menéndez. "Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides." Beilstein Journal of Organic Chemistry 12 (August 8, 2016): 1772–77. http://dx.doi.org/10.3762/bjoc.12.166.

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A sequential three-component process is described, starting from 3-arylmethylene-2,5-piperazinediones and involving a one-pot sequence of reactions achieving regioselective opening of the 2,5-diketopiperazine ring and diastereoselective generation of an aziridine ring. This method allows the preparation of N-unprotected, trisubstituted aziridines bearing a peptide side chain under mild conditions. Their transformation into β-trifluoroacetamido-α-ketoamide and α,β-diketoamide frameworks was also achieved in a single step.

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21

Fehlhammer, Wolf Peter, Eberhard Bär, and Borislav Boyadjiev. "Chemie der Isoblausäure, II Reaktionen von [M(CO)5CNH] (M = Cr, Mo, W) mit Aziridinen: Zyklische Diaminocarbenkomplexe / Chemistry of Hydrogen Isocyanide, II Reactions of [M(CO)5CNH] (M = Cr, Mo, W) with Aziridines: Cyclic Diaminocarbene Complexes." Zeitschrift für Naturforschung B 41, no. 8 (August 1, 1986): 1023–27. http://dx.doi.org/10.1515/znb-1986-0816.

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Abstract The hydrogen isocyanide complexes [M (CO)5CNH] (M = Cr, Mo, W) have been treated with the aziridines R [xxx] H2 (R = H, R’ = H, Me, Et; R = Me, R’ = H) to give imidazolidin-2-ylidene complexes. The same type of ligand forms on addition of aziridine to the electrophilic isocyanide group in [FpCNPh]+ in the presence of Br−, IR, 1H NMR, 13C NMR and mass spectra of the new compounds are reported.

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22

Wang, Chengzhuo, Ning Chen, Zhanhui Yang, and Jiaxi Xu. "Y(OTf)3-Salazin-Catalyzed Asymmetric Aldol Condensation." Molecules 29, no. 9 (April 25, 2024): 1963. http://dx.doi.org/10.3390/molecules29091963.

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The chiral aziridine-containing vicinal iminophenol tridentate ligands (named salazins) are a class of readily prepared chiral ligands from enantiopure aziridines and salicylaldehydes. Their scandium and yttrium triflate complexes show excellent reactivity and enantioselectivities in the catalytic asymmetric aldol condensation of electron-deficient aromatic aldehydes and ketones, including acetone and cycloalkanones. The stereoselectivity is rationalized to the strong π–stacking interaction between aromatic aldehydes and the vicinal iminophenol group in the chiral ligands.

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23

Roedel, J. Nicolas, Roman Bobka, Max Pfister, Martin Rieger, Bernd Neumann, and Ingo-Peter Lorenz. "Synthesis and Structural Characterization of Bis(aziridine) Cobalt(II), Zinc(II) and Palladium(II) Complexes." Zeitschrift für Naturforschung B 62, no. 8 (August 1, 2007): 1095–101. http://dx.doi.org/10.1515/znb-2007-0812.

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The reactions of anhydrous metal chlorides MCl2 [M = Co(II), Zn(II), Pd(II)] with aziridines (az) in CH2Cl2 at r. t. in a 1 : 5 molar ratio afforded the bis(aziridine)dichloro complexes M(az)2Cl2. After purification, all complexes were fully characterized. The solid state structures were determined using single crystal X-ray diffraction, and showed tetrahedral coordination geometries for the Co(II) and Zn(II) centers and trans-configurated square planar geometries for Pd(II).

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24

Ranu, Brindaban C., Laksmikanta Adak, and Subhash Banerjee. "Efficient regio- and stereo-selective cleavage of aziridines and epoxides using an ionic liquid as reagent and reaction medium." Canadian Journal of Chemistry 85, no. 5 (May 1, 2007): 366–71. http://dx.doi.org/10.1139/v07-040.

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Ionic liquids, containing a variety of functionalities such as halo, azido, and thiocyano, efficiently cleave aziridines and epoxides to the corresponding products in high yields. The cleavages are regio- and stereo-selective. The reactions are complete in 1 h at 60 °C and do not require any other catalyst or organic solvent. Thus, a convenient synthetic route to 1,2-haloamines, 1,2-azidoamines, 1,2-thiocyanoamines, 1,2-azidoalcohols, and 1,2-thiocyanoalcohols is developed.Key words: aziridine, epoxide, ionic liquid, cleavage, regioselectivity, stereoselectivity

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25

Buchcic-Szychowska, Aleksandra, Justyna Adamczyk, Lena Marciniak, Adam Marek Pieczonka, Anna Zawisza, Stanisław Leśniak, and Michał Rachwalski. "Efficient Asymmetric Simmons-Smith Cyclopropanation and Diethylzinc Addition to Aldehydes Promoted by Enantiomeric Aziridine-Phosphines." Catalysts 11, no. 8 (August 13, 2021): 968. http://dx.doi.org/10.3390/catal11080968.

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During an implementation of current research, a set of optically pure chiral aziridines and aziridine imines bearing a phosphine moiety was prepared with high values of chemical yield. The above chiral heteroorganic derivatives were tested for catalytic utility as chiral ligands in asymmetric Simmons-Smith cyclopropanation and asymmetric diethylzinc addition to various aldehydes. Most of the desired products were formed in high chemical yields, with satisfactory values of enantiomeric excess (sometimes more than 90%) and diastereomeric ratios (in case of cyclopropanation reaction).

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26

Buchcic-Szychowska, Aleksandra, Anna Zawisza, Stanisław Leśniak, and Michał Rachwalski. "Highly Efficient Asymmetric Morita–Baylis–Hillman Reaction Promoted by Chiral Aziridine-Phosphines." Catalysts 12, no. 4 (March 31, 2022): 394. http://dx.doi.org/10.3390/catal12040394.

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Continuing our research on the use of organophosphorus derivatives of aziridines in asymmetric synthesis and expanding the scope of their applicability, chiral aziridine-phosphines obtained earlier in our laboratory were used as chiral catalysts in the asymmetric Morita–Baylis–Hillman reaction of methyl vinyl ketone and methyl acrylate with various aromatic aldehydes. The desired chiral products were formed in moderate to high chemical yields and with enantiomeric excess reaching value of 98% ee in some cases. The use of catalysts being pairs of enantiomers led to the desired products with opposite absolute configurations.

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27

Pacuła-Miszewska, Agata J., Anna Laskowska, Anna Kmieciak, Mariola Zielińska-Błajet, Marek P. Krzemiński, and Jacek Ścianowski. "Chiral Aziridine Sulfide N(sp3),S-Ligands for Metal-Catalyzed Asymmetric Reactions." Symmetry 13, no. 3 (March 19, 2021): 502. http://dx.doi.org/10.3390/sym13030502.

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A series of new bidentate N,S-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition reactions (up to 94.2:5.8) was obtained using the aziridine ligand bearing a p-nitro phenyl sulfide group. Collected results reveal a specific electronic effect that, by the presence of particular electron-donating or electron-withdrawing groups in the PhS- moiety, influences the σ-donor–metal binding and the enantioselectivity of the catalyzed reactions.

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28

Peipiņš, Vilnis, Krista Suta, and Māris Turks. "Study on Synthesis of N-Protected 2-Triazolyl Azetidines." Key Engineering Materials 762 (February 2018): 19–24. http://dx.doi.org/10.4028/www.scientific.net/kem.762.19.

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Azetidine derivatives are interesting scaffolds in terms of medicinal chemistry. They can be regarded as structural homologs of aziridines. Herein we report synthetic approach to the novel N-protected 2-triazolyl azetidines which are structurally similar to our previously described aziridine derivatives with matrix metalloproteinase-2 inhihbitory activities. The synthetic rout includes ring closing of ethyl 2,4-dibromobutanoate, selective reduction of ester to aldehyde and transformation of the latter to terminal alkyne by Ohira-Bestmann reagent. 2-Ethynyl azetidines as key intermediates were transformed into triazole derivatives by Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction.

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29

Iuliis, Marco Zimmer De, Iain DG Watson, Andrei K. Yudin, and Robert H. Morris. "A DFT investigation into the origin of regioselectivity in palladium-catalyzed allylic amination." Canadian Journal of Chemistry 87, no. 1 (January 1, 2009): 54–62. http://dx.doi.org/10.1139/v08-078.

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The addition of amines or aziridines to prenylacetate is catalyzed by palladium phosphine complexes. The first-formed products have recently been shown to be the branched olefins R2NCMe2CH=CH2, R = alkyl, or R2 = 1,2-C6H10, for example. DFT calculations using the MPW1K functional were performed on reactions of the suspected intermediate η3-prenyl complex [Pd(η3-Me2CCHCH2)(PH3)2]+ with dimethylamine and ethylene imine. The activation barrier for the nucleophilic attack by the amine or the aziridine is calculated to be similar for either the sterically hindered site of the π-allyl ligand to produce the branched olefin complex or the unhindered site to give the linear olefin complex. Therefore, these calculations do not reveal the experimentally observed preference for attack. This observation, along with the experimental observation of lack of isomerization of the branched olefin product of the aziridine reactions, appears to rule out the intermediacy of a π-allyl complex [Pd(η3-Me2CCHCH2)L2]+, L = phosphine or L2 = diphosphine in the C–N bond-forming reaction.Key words: allyl palladium, amine, aziridine, DFT, mechanism, catalysis.

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30

Keniche, Assia, Samia Bellifa, Hafida Hassaine, and Joseph Kajima Mulengi. "Development of new antibacterial agents." Medical Technologies Journal 1, no. 2 (June 8, 2017): 31–32. http://dx.doi.org/10.26415/2572-004x-vol1iss2p31-32.

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Background: Antibiotics, as miraculous drugs, have been used extensively to confront fatal infection, even without prescriptions. However, the inappropriate and disproportionate use of antibiotics have led to the emergence of new drug-resistant bacteria1, which causes a high risk of serious diseases and dramatically aggravates the clinical complications in hospitals. Methods: By using the peptide coupling protocol, a simple straightforward synthesis of functionalized aziridines has been developed. By means of this synthetic strategy from readily available N-phtaloyl acide and 2-methylbenzosulfonate aziridine using DCC as coupling agent, new tosylates aziridines could be obtained. The coupling reactions occurred without a ring opening of the three membered ring. Results: This work describes new results of our ongoing research targeting new derivatives of biological interests. All the compounds were screened for their antibacterial activity; they all showed comparable moderate to good growth inhibitory activity with reference to tetracyclin and gentamicin. Conclusion: In conclusion, we reported the synthesis and a preliminary antibacterial evaluation of novel functionalized tosylaziridines. The synthetic strategy relies on the coupling reactions between tosylaziridines and amino acids. Moreover, and besides showing interesting antibacterial activities, the series of novel compounds can be further improved to serve as potential drug against nosocomial diseases.

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31

Bisseret, Philippe, Claire Bouix-Peter, Olivier Jacques, Stéphanie Henriot, and Jacques Eustache. "Sugar-Derived Aziridines: Functionalization via Lithiation of the Aziridine Ring." Organic Letters 1, no. 8 (October 1999): 1181–82. http://dx.doi.org/10.1021/ol990841e.

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32

Kostyanovskii, R. G., G. K. Kadorkina, S. V. Varlamov, I. I. Chervin, and I. K. A. Romero-Maldonado. "2-Aziridino- and 2-diaziridino-3,3-bis(trifluoromethyl)aziridines." Chemistry of Heterocyclic Compounds 24, no. 4 (April 1988): 387–94. http://dx.doi.org/10.1007/bf00478856.

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33

Liu, Xiang, Yu Huang, Xu Meng, Jihui Li, Dong Wang, Yongxin Chen, Dong Tang, and Baohua Chen. "Recent Developments in the Synthesis of Nitrogen-Containing Heterocycles through C–H/N–H Bond Functionalizations and Oxidative Cyclization." Synlett 30, no. 09 (February 22, 2019): 1026–36. http://dx.doi.org/10.1055/s-0037-1611476.

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The synthesis and structure of nitrogen-containing heterocycles are fascinating because these compounds have a great richness of structural, physicochemical, and biological properties. Therefore, the development of improved ways for the synthesis of polyfunctional nitrogen-containing heterocycles continues to be a challenging goal. This account describes developments in the discovery of C–H/N–H bond functionalization and oxidative cyclization procedures for the synthesis of nitrogen-containing heterocycles (aziridines, indoles, indolizines, triazoles, imidazoles, oxazoles, thiazoles, quinoxalines, triazines, and pyridines) in our laboratories during the last 15 years.1 Introduction2 Synthesis of Aziridines3 Synthesis of Indoles and Indolizines4 Synthesis of Triazoles5 Synthesis of Imidazoles6 Synthesis of Oxazoles and Thiazoles7 Synthesis of Quinoxalines, Triazines, and Pyridines8 Conclusion and Outlook

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34

Wu, Qiuyue, and Jiaxi Xu. "Regio- and stereoselective synthesis of thiazoline derivatives via the thioketene-induced ring expansion of aziridines." Chemical Communications 58, no. 16 (2022): 2714–17. http://dx.doi.org/10.1039/d1cc06535a.

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Disubstituted thiazolines are regio- and stereoselectively synthesized from 4-substituted 1,2,3-thiadiazoles and 2-substituted aziridines in the presence of a base via the thioketene-induced ring expansion of aziridines.

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35

Kowalczyk, Aleksandra, Adam M. Pieczonka, Hassan Kassassir, Michał Rachwalski, and Paweł Stączek. "A Study on the Biological Activity of Optically Pure Aziridine Phosphines and Phosphine Oxides." Molecules 29, no. 7 (March 22, 2024): 1430. http://dx.doi.org/10.3390/molecules29071430.

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A series of optically pure aziridine phosphines and their corresponding phosphine oxides were synthesized through established chemical methodologies. The compounds were systematically investigated for their biological properties. Notably, all synthesized compounds demonstrated moderate antibacterial activity only against the reference strain of Staphylococcus aureus. However, compounds 5 and 7 exhibited noteworthy cell viability inhibition of human cervical epithelioid carcinoma HeLa cells and endometrial adenocarcinoma Ishikawa cells. Further studies of these compounds revealed additional biological effects, including disruption of the cell membrane in high concentrations, cell cycle arrest in the S phase, and the induction of reactive oxygen species (ROS). Comparative analysis of the two classes of chiral organophosphorus derivatives of aziridines indicated that chiral phosphine oxides displayed significantly higher biological activity. Consequently, these findings suggest that chiral phosphine oxides may be potential candidates for the development of anticancer drugs. In light of the significant interest in preparations whose structure is based on a three-membered aziridine ring in terms of potential anticancer therapy, this research fits into the current research trend and should constitute a valuable addition to the current state of knowledge and the existing library of aziridine derivatives with anticancer properties.

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36

Hodgson, David M., Steven P. Hughes, Amber L. Thompson, and Tom D. Heightman. "Terminal Aziridines by α-Deprotonation/Electrophile Trapping of N-Protected Aziridine." Organic Letters 10, no. 16 (August 2008): 3453–56. http://dx.doi.org/10.1021/ol801224g.

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37

Wang, Ping-An. "Organocatalyzed enantioselective desymmetrization of aziridines and epoxides." Beilstein Journal of Organic Chemistry 9 (August 15, 2013): 1677–95. http://dx.doi.org/10.3762/bjoc.9.192.

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Enantioselective desymmetrization of meso-aziridines and meso-epoxides with various nucleophiles by organocatalysis has emerged as a cutting-edge approach in recent years. This review summarizes the origin and recent developments of enantioselective desymmetrization of meso-aziridines and meso-epoxides in the presence of organocatalysts.

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38

Jarvis, Ashley N., Andrew B. McLaren, Helen M. I. Osborn, and Joseph Sweeney. "Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines." Beilstein Journal of Organic Chemistry 9 (May 2, 2013): 852–59. http://dx.doi.org/10.3762/bjoc.9.98.

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Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with α-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity.

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39

Tian, Duanshuai, Henian Peng, Ziyue Liu, and Wenjun Tang. "Optically active N-alkyl aziridines via stereospecific reductive cyclization of α-mesylated acetamides." Organic Chemistry Frontiers 5, no. 18 (2018): 2723–27. http://dx.doi.org/10.1039/c8qo00774h.

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An efficient method for the synthesis of optically active N-alkyl aziridines has been realized for the first time by stereospecific reductive cyclization of optically active α-mesylated acetamides. A series of optically active N-alkyl aziridines are prepared in moderate to good yields and excellent ees.

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40

Ghosal, Nirnita, Sachinta Mahato, Rana Chatterjee, Sougata Santra, Grigory Zyryanov, and Adinath Majee. "A Mild and Efficient Method for the Syntheses and Regioselective Ring-Opening of Aziridines." SynOpen 01, no. 01 (March 2017): 0015–23. http://dx.doi.org/10.1055/s-0036-1588809.

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We have developed a new synthetic method for the synthesis of aziridines using Chloramine-T as an effective reagent in the presence of NH2OH·HCl and NaIO4. We found that the same combination of NH2OH·HCl and NaIO4 is also very effective for nucleophilic ring opening of aziridines.

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41

Hodgson, David M., Philip G. Humphreys, and John G. Ward. "Substituted Aziridines by Lithiation−Electrophile Trapping of Terminal Aziridines." Organic Letters 7, no. 6 (March 2005): 1153–56. http://dx.doi.org/10.1021/ol050060f.

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42

Caiazzo, Aldo, Shadi Dalili, C. Picard, M. Sasaki, T. Siu, and A. K. Yudin. "New methods for the synthesis of heterocyclic compounds." Pure and Applied Chemistry 76, no. 3 (January 1, 2004): 603–13. http://dx.doi.org/10.1351/pac200476030603.

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Due to frequent occurrence of nitrogen-containing groups among the biologically active compounds, chemoselective functionalization of organic molecules with nitrogen-containing functional groups is an important area of organic synthesis. We have proposed and implemented a new strategy toward design of nitrogen-transfer reactions on inert electrode surfaces with a particular focus on the generation and trapping of highly reactive nitrogen-transfer agents. A wide range of structurally dissimilar olefins can be readily transformed into the corresponding aziridines. The resulting aziridines are precursors to a range of catalysts via nucleophilic ring-opening with diaryl- and dialkyl phosphines. Another strategy explored in the context of oxidative nitrogen transfer is cycloamination of olefins using NH aziridines.

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43

More, Satish S., T. Krishna Mohan, Y. Sateesh Kumar, U. K. Syam Kumar, and Navin B. Patel. "Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters." Beilstein Journal of Organic Chemistry 7 (June 20, 2011): 831–38. http://dx.doi.org/10.3762/bjoc.7.95.

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A novel synthetic methodology has been developed for the synthesis of diethyl 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates (also called 2-substituted pyrroline-4,5-dihydro-3,3-dicarboxylic acid diethyl esters) by iodide ion induced ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters in very good to excellent yields under mild reaction conditions. The electronic and steric impact of the substituents on the kinetics of ring expansion of N-vinyl aziridines to pyrrolines has been studied. Various diversely substituted novel pyrroline derivatives have been synthesized by this methodology and the products can be used as key intermediates in the synthesis of substituted pyrrolines, pyrroles and pyrrolidines.

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44

ZURER, PAMELA. "AZIRIDINES VIA ELECTROCHEMISTRY." Chemical & Engineering News Archive 80, no. 4 (January 28, 2002): 14. http://dx.doi.org/10.1021/cen-v080n004.p014.

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45

Lork, Andre, Gary Gard, Michael Hare, R�diger Mews, Wolf-Dieter Stohrer, and Rolf Winter. "N-chlorosulfenyl-aziridines." Journal of the Chemical Society, Chemical Communications, no. 12 (1992): 898. http://dx.doi.org/10.1039/c39920000898.

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46

Bergmeier, Stephen C., and Punit P. Seth. "Formation of Scalemic Aziridines via the Nucleophilic Opening of Aziridines." Journal of Organic Chemistry 62, no. 8 (April 1997): 2671–74. http://dx.doi.org/10.1021/jo962307f.

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47

Yang, Yunhan, Fenji Li, Cuicui Yang, Lijuan Jia, Lijuan Yang, Futing Xia, and Jinhui Peng. "Effect of Substitution for Insertion of CO2 into Epoxides and Aziridines: An Ab Initio Study." Australian Journal of Chemistry 73, no. 1 (2020): 30. http://dx.doi.org/10.1071/ch19296.

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The insertion of CO2 into epoxides and aziridines has been studied using density functional theory (B3LYP) and ab initio (MP2) methods, and the effect of substitution for the two reactions are further explored. It is found that the reactivity of epoxides and aziridines are similar, and insertion of CO2 proceeds through a concerted mechanism. The substitutions of methyl and phenyl does not change the reaction mechanism, but the transition state for the substitution on the attacking position becomes loose with a lower free energy barrier. The substitutions of methyl and phenyl decrease the free energy barrier, with phenyl substitution having a greater affect. The results also show that the free energy barriers for the insertions of CO2 into aziridines are ~10kcalmol−1 lower than the corresponding reactions of CO2 with epoxides.

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48

Tan, Xing-Fa, Fa-Guang Zhang, and Jun-An Ma. "Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis." Beilstein Journal of Organic Chemistry 16 (April 7, 2020): 638–44. http://dx.doi.org/10.3762/bjoc.16.60.

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A diastereo- and enantioselective approach to access chiral CF2-functionalized aziridines from difluorodiazoethyl phenyl sulfone (PhSO2CF2CHN2) and in situ-formed aldimines is described. This multicomponent reaction is enabled by a combined strong Brønsted acid catalytic platform consisting of a chiral disulfonimide and 2-carboxyphenylboronic acid. The optical purity of the obtained CF2-substituted aziridines could be further improved by a practical dissolution–filtration procedure.

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49

Borodina, O., A. Novikov, G. Zyryanov, and E. Bartashevich. "Theoretical evaluation of phenyl-substituted aziridines, azirines and epoxides reactivity." Bulletin of the South Ural State University series "Chemistry" 15, no. 4 (2023): 149–59. http://dx.doi.org/10.14529/chem230406.

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The reactivity of three-membered heterocycles such as phenyl-substituted aziridines, azirines, epoxides was studied in comparison with styrenes, azomethines and carbonyl com-pounds which are most often used in organic synthesis in nucleophilic and electrophilic reactions. In accordance with electronic reactivity indices of nucleophilicity and electrophilicity calculated on the base of DFT approach, the substituted molecules of azirines, aziridines, and epoxides ex-hibit the similar reactivity to aldehydes and styrenes. In all cases, our predictions were checked against the experimental observations given in literature. All considered compounds mainly characterizes by the properties of medium-strength electrophiles. Aziridines, azirines, epoxides with two aryl groups show the best electrophilic properties. This observation can be used in predictions of reactivity for these classes of compounds. Among three-membered heterocycles, the best nucleophilic properties were observed for substituted epoxy cycles. We have found that the dual descriptor based on Fukui functions cannot be recommended for predictions the reactivity of aziridines and epoxides. The values of the dual descriptor on both carbon atoms in three-membered ring significantly differ, while the experimental data on nucleophilic addition indicate that the reaction proceeds at both carbon atoms. Nevertheless, for phenyl-substituted azirines, the descriptor based on Fukui functions shows its effectiveness quite well.

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50

Schad, Caroline, Ulrike Baum, Benjamin Frank, Uwe Dietzel, Felix Mattern, Carlos Gomes, Alicia Ponte-Sucre, Heidrun Moll, Uta Schurigt, and Tanja Schirmeister. "Development of a New Antileishmanial Aziridine-2,3-Dicarboxylate-Based Inhibitor with High Selectivity for Parasite Cysteine Proteases." Antimicrobial Agents and Chemotherapy 60, no. 2 (November 23, 2015): 797–805. http://dx.doi.org/10.1128/aac.00426-15.

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ABSTRACTLeishmaniasis is one of the major neglected tropical diseases of the world. Druggable targets are the parasite cysteine proteases (CPs) of clan CA, family C1 (CAC1). In previous studies, we identified two peptidomimetic compounds, the aziridine-2,3-dicarboxylate compounds 13b and 13e, in a series of inhibitors of the cathepsin L (CL) subfamily of the papain clan CAC1. Both displayed antileishmanial activityin vitrowhile not showing cytotoxicity against host cells. In further investigations, the mode of action was characterized inLeishmania major. It was demonstrated that aziridines 13b and 13e mainly inhibited the parasitic cathepsin B (CB)-like CPC enzyme and, additionally, mammalian CL. Although these compounds induced cell death ofLeishmaniapromastigotes and amastigotesin vitro, the induction of a proleishmanial T helper type 2 (Th2) response caused by host CL inhibition was observedin vivo. Therefore, we describe here the synthesis of a new library of more selective peptidomimetic aziridine-2,3-dicarboxylates discriminating between host and parasite CPs. The new compounds are based on 13b and 13e as lead structures. One of the most promising compounds of this series is compound s9, showing selective inhibition of the parasite CPsLmaCatB (a CB-like enzyme ofL. major; also namedL. majorCPC) andLmCPB2.8 (a CL-like enzyme ofLeishmania mexicana) while not affecting mammalian CL and CB. It displayed excellent leishmanicidal activities againstL. majorpromastigotes (50% inhibitory concentration [IC50] = 37.4 μM) and amastigotes (IC50= 2.3 μM). In summary, we demonstrate a new selective aziridine-2,3-dicarboxylate, compound s9, which might be a good candidate for futurein vivostudies.

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