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Journal articles on the topic 'Ring opening of azirine and aziridines'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Carramiñana, Victor, Ana M. Ochoa de Retana, Francisco Palacios, and Jesús M. de los Santos. "Synthesis of α-Aminophosphonic Acid Derivatives Through the Addition of O- and S-Nucleophiles to 2H-Azirines and Their Antiproliferative Effect on A549 Human Lung Adenocarcinoma Cells." Molecules 25, no. 15 (July 22, 2020): 3332. http://dx.doi.org/10.3390/molecules25153332.

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This work reports a straightforward regioselective synthetic methodology to prepare α-aminophosphine oxides and phosphonates through the addition of oxygen and sulfur nucleophiles to the C–N double bond of 2H-azirine derivatives. Determined by the nature of the nucleophile, different α-aminophosphorus compounds may be obtained. For instance, aliphatic alcohols such as methanol or ethanol afford α-aminophosphine oxide and phosphonate acetals after N–C3 ring opening of the intermediate aziridine. However, addition of 2,2,2-trifluoroethanol, phenols, substituted benzenthiols or ethanethiol to 2H-azirine phosphine oxides or phosphonates yields allylic α-aminophosphine oxides and phosphonates in good to high general yields. In some cases, the intermediate aziridine attained by the nucleophilic addition of O- or S-nucleophiles to the starting 2H-azirine may be isolated and characterized before ring opening. Additionally, the cytotoxic effect on cell lines derived from human lung adenocarcinoma (A549) and non-malignant cells (MCR-5) was also screened. Some α-aminophosphorus derivatives exhibited very good activity against the A549 cell line in vitro. Furthermore, selectivity towards cancer cell (A549) over non-malignant cells (MCR-5) has been detected in almost all compounds tested.

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2

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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3

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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4

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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5

Cytlak, T., M. Saweliew, M. Kubicki, and H. Koroniak. "Synthesis of trifluoromethyl γ-aminophosphonates by nucleophilic aziridine ring opening." Organic & Biomolecular Chemistry 13, no. 39 (2015): 10050–59. http://dx.doi.org/10.1039/c5ob01411e.

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6

Gleede, Tassilo, Louis Reisman, Elisabeth Rieger, Pierre Canisius Mbarushimana, Paul A. Rupar, and Frederik R. Wurm. "Aziridines and azetidines: building blocks for polyamines by anionic and cationic ring-opening polymerization." Polymer Chemistry 10, no. 24 (2019): 3257–83. http://dx.doi.org/10.1039/c9py00278b.

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7

Chakraborty Ghosal, Nirnita, Sougata Santra, Sudarshan Das, Alakananda Hajra, Grigory V. Zyryanov, and Adinath Majee. "Organocatalysis by an aprotic imidazolium zwitterion: regioselective ring-opening of aziridines and applicable to gram scale synthesis." Green Chemistry 18, no. 2 (2016): 565–74. http://dx.doi.org/10.1039/c5gc01323b.

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8

Bhandari, Sonal, Sravani Sana, Vandana Lahoti, Ramya Tokala, and Nagula Shankaraiah. "Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines." RSC Advances 10, no. 27 (2020): 16101–9. http://dx.doi.org/10.1039/d0ra00684j.

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Herein, we report a facile tandem approach for the synthesis of both spiro-oxindole-fused pyrroloindolines and benzofurano-pyrrolidines via a Lewis acid-catalyzed domino ring-opening annulation using activated spiro-aziridines and heteroarenes.

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9

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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10

Siebert, Matthew R., Andrei K. Yudin, and Dean J. Tantillo. "Cycloaddition/Ring Opening Reaction Sequences ofN-Alkenyl Aziridines: Influence of the Aziridine Nitrogen on Stereoselectivity." Organic Letters 10, no. 1 (January 2008): 57–60. http://dx.doi.org/10.1021/ol702623d.

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11

Atkinson, Robert S., Andrew P. Ayscough, William T. Gattrell, and Tony M. Raynham. "Acid-catalysed ring-opening of N-(3, 4-dihydro-4-oxoquinazolin-3-yl)-substituted aziridines: aziridine ring-opening with retention of configuration." Tetrahedron Letters 39, no. 24 (June 1998): 4377–80. http://dx.doi.org/10.1016/s0040-4039(98)00705-9.

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12

ATKINSON, R. S., A. P. AYSCOUGH, W. T. GATTRELL, and T. M. RAYNHAM. "ChemInform Abstract: Acid-Catalyzed Ring-Opening of N-(3,4-Dihydro-4-oxoquinazolin-3-yl)-substituted Aziridines: Aziridine Ring-Opening with Retention of Configuration." ChemInform 29, no. 35 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199835195.

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13

Wang, Jin-Yuan, Yuan Hu, De-Xian Wang, Jie Pan, Zhi-Tang Huang, and Mei-Xiang Wang. "Unprecedented carbon–carbon bond cleavage in nucleophilic aziridine ring opening reaction, efficient ring transformation of aziridines to imidazolidin-4-ones." Chem. Commun., no. 4 (2009): 422–24. http://dx.doi.org/10.1039/b816007d.

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14

Stamm, Helmut, and Dieter Speth. "Reactions with aziridines, 51: Ring opening ofcis-2-Benzyl-3-phenyl-1-(phenylsulfonyl)aziridine by alkoxide. The first eliminative fission of an aziridine with uncharged nitrogen." Chemische Berichte 122, no. 9 (September 1989): 1795–97. http://dx.doi.org/10.1002/cber.19891220928.

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15

Ghosal, Nirnita Chakraborty, Sougata Santra, Grigory V. Zyryanov, Alakananda Hajra, and Adinath Majee. "Conversion of aziridines to oxazolidines through geminal difunctionalization of vinyl arenes or by tandem ring-opening/closing reaction of aziridine itself." Tetrahedron Letters 57, no. 31 (August 2016): 3551–55. http://dx.doi.org/10.1016/j.tetlet.2016.06.119.

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16

Savoia, Diego, Giuseppe Alvaro, Romano Di Fabio, Andrea Gualandi, and Claudio Fiorelli. "Asymmetric Synthesis of 2-(2-Pyridyl)aziridines from 2-Pyridineimines Bearing StereogenicN-Alkyl Substituents and Regioselective Opening of the Aziridine Ring." Journal of Organic Chemistry 71, no. 25 (December 2006): 9373–81. http://dx.doi.org/10.1021/jo0614137.

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17

Chen, Xingpeng, Chao Lin, Hongguang Du, and Jiaxi Xu. "Efficient Direct Synthesis of Aziridine‐Containing Chiral Tridentate Ligands by the Iminium‐Mediated Self‐Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes." Advanced Synthesis & Catalysis 361, no. 7 (February 22, 2019): 1647–61. http://dx.doi.org/10.1002/adsc.201801545.

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18

Vederas, John C. "2005 Alfred Bader Award Lecture Diaminopimelate and lysine biosynthesis - An antimicrobial target in bacteria." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1197–207. http://dx.doi.org/10.1139/v06-072.

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The development of bacterial resistance to current antibiotic therapy has stimulated the search for novel antimicrobial agents. The essential peptidoglycan cell wall layer in bacteria is the site of action of many current drugs, such as β-lactams and vancomycin. It is also a target for a number of very potent bacterially produced antibiotic peptides, such as nisin A and lacticin 3147, both of which are highly posttranslationally modified lantibiotics that act by binding to lipid II, the peptidoglycan precursor. Another set of potential targets for antibiotic development are the bacterial enzymes that make precursors for lipid II and peptidoglycan, for example, those in the pathway to diamino pimelic acid (DAP) and its metabolic product, L-lysine. Among these, DAP epimerase is a unique nonpyridoxal phosphate (PLP) dependent enzyme that appears to use two active site thiols (Cys73 and Cys217) as a base and an acid to depro tonate the α-hydrogen of LL-DAP or meso-DAP from one side and reprotonate from the other. This process cannot be easily duplicated in the absence of the enzyme. A primary goal of our work was to generate inhibitors of DAP epi merase that would accurately mimic the natural substrates (meso-DAP and LL-DAP) in the enzyme active site and, through crystallographic analysis, provide insight into mechanism and substrate specificity. A series of aziridine-containing DAP analogs were chemically synthesized and tested as inhibitors of DAP epimerase from Haemophilus influenzae. Two diastereomers of 2-(4-amino-4-carboxybutyl)aziridine-2-carboxylic acid (AziDAP) act as rapid irreversible inactivators of DAP epimerase; the AziDAP analog of LL-DAP reacts selectively with the sulfhydryl of Cys73, whereas the corresponding analog of meso-DAP reacts with Cys217. AziDAP isomers are too unstable to be useful antibiotics. However, mass spectral and X-ray crystallographic analyses of the inactivated enzymes confirm that the thiol attacks the methylene group of the aziridine with concomitant ring opening to give a DAP analog bound in the active site. Further crystallographic analyses should yield useful mechanistic insights.Key words: enzyme mechanism, enzyme inhibition, antibiotics, aziridines, amino acids.

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19

Choi, Jieun, Taehwan Yu, and Hyun-Joon Ha. "Alkylative Aziridine Ring-Opening Reactions." Molecules 26, no. 6 (March 18, 2021): 1703. http://dx.doi.org/10.3390/molecules26061703.

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In this study, the highly strained three-membered aziridine ring was successfully activated as the aziridinium ion by alkylation of the ring nitrogen with a methyl, ethyl or allyl group, which was followed by ring opening with external nucleophiles such as acetate and azide. Such alkylative aziridine ring opening provides an easy route for the synthesis of various N-alkylated amine-containing molecules with concomitant introduction of an external nucleophile at either its α- or β-position.

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20

Jang, Hyeon-Jae, Jae Tak Lee, and Hyo Jae Yoon. "Aziridine in polymers: a strategy to functionalize polymers by ring-opening reaction of aziridine." Polymer Chemistry 6, no. 18 (2015): 3387–91. http://dx.doi.org/10.1039/c5py00266d.

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21

Rostovskii, Nikolai V., Mikhail S. Novikov, Alexander F. Khlebnikov, Galina L. Starova, and Margarita S. Avdontseva. "Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization." Beilstein Journal of Organic Chemistry 11 (March 2, 2015): 302–12. http://dx.doi.org/10.3762/bjoc.11.35.

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Strained azirinium ylides derived from 2H-azirines and α-diazoketones under Rh(II)-catalysis can undergo either irreversible ring opening across the N–C2 bond to 2-azabuta-1,3-dienes that further cyclize to 2H-1,4-oxazines or reversibly undergo a 1,5-cyclization to dihydroazireno[2,1-b]oxazoles. Dihydroazireno[2,1-b]oxazoles derived from 3-aryl-2H-azirines and 3-diazoacetylacetone or ethyl diazoacetoacetate are able to cycloadd to acetyl(methyl)ketene generated from 3-diazoacetylacetone under Rh(II) catalysis to give 4,6-dioxa-1-azabicyclo[3.2.1]oct-2-ene and/or 5,7-dioxa-1-azabicyclo[4.3.1]deca-3,8-diene-2-one derivatives. According to DFT calculations (B3LYP/6-31+G(d,p)), the cycloaddition can involve two modes of nucleophilic attack of the dihydroazireno[2,1-b]oxazole intermediate on acetyl(methyl)ketene followed by aziridine ring opening into atropoisomeric oxazolium betaines and cyclization. Azirinium ylides generated from 2,3-di- and 2,2,3-triaryl-substituted azirines give rise to only 2-azabuta-1,3-dienes and/or 2H-1,4-oxazines.

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22

Kroutil, Jiří, Jindřich Karban, Tomáš Trnka, Miloš Buděšínský, and Miloslav Černý. "Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening." Collection of Czechoslovak Chemical Communications 67, no. 12 (2002): 1805–19. http://dx.doi.org/10.1135/cccc20021805.

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The aziridine ring opening of N-tosylepimino carbohydrates 1-6 having D-allo, D-manno, D-galacto and D-talo configurations with benzyl alcohol, benzylamine and phenylmethanethiol afforded 2-, 3- and 4-O-benzyl-, benzylsulfanyl and benzylamino derivatives of 1,6-anhydro-β-D-hexopyranoses of D-gluco, D-galacto and D-manno configurations 7-23 in 44-99% yields. Hexenopyranoses 24-26 were prepared from tosylepimino carbohydrates 1, 4 and 5 by intramolecular rearrangement of the aziridine ring.

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23

Zujewska, T., and B. Bachowska. "Benzonaphthyridine N-Oxides as 1,3-Dipoles." Australian Journal of Chemistry 49, no. 4 (1996): 523. http://dx.doi.org/10.1071/ch9960523.

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Benzonaphthyridine N-oxides give N-ylides with dimethyl acetylenedicarboxylate at room temperature, most probably by 1,3-dipolar cycloaddition followed by ring contraction to form an aziridine derivative, and ring opening.

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24

Chung, Benjamin K. W., Christopher J. White, Conor C. G. Scully, and Andrei K. Yudin. "The reactivity and conformational control of cyclic tetrapeptides derived from aziridine-containing amino acids." Chemical Science 7, no. 11 (2016): 6662–68. http://dx.doi.org/10.1039/c6sc01687a.

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25

Alluri, Santosh R., and Patrick J. Riss. "Stereospecific radiosynthesis of 3-fluoro amino acids: access to enantiomerically pure radioligands for positron emission tomography." Organic & Biomolecular Chemistry 16, no. 13 (2018): 2219–24. http://dx.doi.org/10.1039/c8ob00184g.

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26

Guasch, Joan, Yolanda Díaz, M. Isabel Matheu, and Sergio Castillón. "Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates." Chem. Commun. 50, no. 55 (2014): 7344–47. http://dx.doi.org/10.1039/c4cc01312c.

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27

Ondrus, Theodore A., Purushottam R. Pednekar, and Edward E. Knaus. "Some reactions of 1-methyl-1,2-dihydropyridines with organic azides. Synthesis and reactions of 1,2,5,6-tetrahydropyridylidene-2-cyan(sulfon)amides and piperidylidene-2-cyan(sulfon)amides." Canadian Journal of Chemistry 63, no. 9 (September 1, 1985): 2362–68. http://dx.doi.org/10.1139/v85-391.

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The regiospecific 1,3-dipolar cycloaddition reaction of 1,2-dihydropyridines 2 with organic azides 3 affords 2,7-diazabicyclo[4.1.0]hept-4-enes 4. Treatment of 4a with neutral aluminum oxide opened the aziridine ring to afford the 1,2,5,6-tetrahydropyridylidene-2-cyanamide 5. Catalytic hydrogenation of 4 and 5 using palladium-on-charcoal and hydrogen yielded the 1-methyl-2-piperidylidenes 6. Oxidation of 1-methyl-1,2,5,6-tetrahydropyridylidene-2-cyanamide (5) with alkaline hydrogen peroxide yielded the oxirane 7 arising from epoxidation of the 3,4-olefenic bond, whereas oxidation of the bicyclic aziridine 4a with m-chloroperbenzoic acid resulted in epoxidation of the 4,5-olefenic bond and opening of the aziridine ring to give the oxirane 3-methyl-3-aza-7-oxabicyclo[4.1.0]heptylidene-4-cyanamide (10). Base-catalyzed abstraction of the C-3 proton of 1-methyl-2-piperidylidenes 6 yielded the 3-lithio analogs which, after bromination, were converted to the target compounds 18 upon condensation with 4-[(2-aminoethyl)thiomethyl]-5-methylimidazole.

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28

Allan, RD, and HW Tran. "Facile Synthesis of β-Phenylethylamine Derivatives Related to Baclofen via Aziridine Ring Opening." Australian Journal of Chemistry 43, no. 6 (1990): 1123. http://dx.doi.org/10.1071/ch9901123.

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Nucleophilic ring opening of the protonated salt of 2-(4-chlorophenyl ) aziridine with substituted thiols provides a very simple route to β- phenylethylamine derivatives which are analogues of the GABAB receptor agonist baclofen and its antagonists phaclofen and saclofen.

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29

Bělohradský, Martin, Luděk Ridvan, and Jiří Závada. "Synthesis of Homochiral Acyclic Mono- and Bis(α-amino acid)s with Oligo(oxyethylene) Chains." Collection of Czechoslovak Chemical Communications 68, no. 7 (2003): 1319–25. http://dx.doi.org/10.1135/cccc20031319.

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Synthesis of homochiral α-amino acids 3a-3e and bis(α-amino acid)s 4a-4e via BF3·Et2O-catalyzed ring-opening of methyl (S)-1-[(benzyloxy)carbonyl]aziridine-2-carboxylate (7) with oligo(ethylene glycol)s and subsequent acid hydrolysis is reported.

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30

Lee, Won, Hyun-Joon Ha, and Sonhwan Kim. "Asymmetric Synthesis of cis-5-(Aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one." Synthesis 51, no. 04 (November 8, 2018): 885–88. http://dx.doi.org/10.1055/s-0037-1610667.

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The asymmetric synthesis of (3R,5S)-5-(aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one, as the most potent selective inactivator of monoamine B, was successfully achieved by applying a newly developed synthetic method toward the key γ-aminomethyl-γ-lactone via intramolecular aziridine ring opening in 63% overall yield from a commercial starting material.

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31

Sabir, Shekh, Ganesh Kumar, Ved Prakash Verma, and Jawahar L. Jat. "Aziridine Ring Opening: An Overview of Sustainable Methods." ChemistrySelect 3, no. 13 (April 6, 2018): 3702–11. http://dx.doi.org/10.1002/slct.201800170.

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32

Ishikawa, Tsutomu. "Aziridine-2-carboxylates: Preparation, Nucleophilic Ring Opening, and Ring Expansion." HETEROCYCLES 85, no. 12 (2012): 2837. http://dx.doi.org/10.3987/rev-12-748.

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33

Nolsøe, Jens, David Riegert, Paul Müller, and David Tanner. "An approach to preparation of trans-DHQs via ring-opening of meso-N-sulfonylaziridines." Collection of Czechoslovak Chemical Communications 76, no. 7 (2011): 815–28. http://dx.doi.org/10.1135/cccc2011013.

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As an approach to the enantioselective synthesis of trans-decahydroquinolines (DHQs), desymmetrization of meso-aziridine (5) with various carbon nucleophiles under catalytic conditions was investigated. By applying TMSCN in the presence of YbCl3 and chiral non-racemic ligands, nitrile 13 was obtained with an ee up to 40%. Nitrile 13 was a key intermediate in a novel route to trans-DHQs.

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34

Heinrich, Markus R., Inés Pérez-Martín, and Samir Z. Zard. "Generation and ring opening of aziridine N-carbonyl radicals." Chemical Communications, no. 47 (2005): 5928. http://dx.doi.org/10.1039/b512956g.

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35

YAHIRO, Nobuhide. "Ring-opening reaction of optically active aziridine in water." NIPPON KAGAKU KAISHI, no. 9 (1989): 1648–51. http://dx.doi.org/10.1246/nikkashi.1989.1648.

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36

Adhikari, Debashis, Aaron W. Miller, Mu-Hyun Baik, and SonBinh T. Nguyen. "Intramolecular ring-opening from a CO2-derived nucleophile as the origin of selectivity for 5-substituted oxazolidinone from the (salen)Cr-catalyzed [aziridine + CO2] coupling." Chemical Science 6, no. 2 (2015): 1293–300. http://dx.doi.org/10.1039/c4sc02785j.

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The (salen)Cr-catalyzed [aziridine + CO₂] coupling to form oxazolidinone was found to exhibit excellent selectivity for the 5-substituted oxazolidinone product in the absence of any cocatalyst.

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37

Ishikawa, Tsutomu. "ChemInform Abstract: Aziridine-2-carboxylates: Preparation, Nucleophilic Ring Opening, and Ring Expansion." ChemInform 44, no. 11 (March 8, 2013): no. http://dx.doi.org/10.1002/chin.201311215.

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38

Kim, Yongeun, Doo-Ha Yoon, Hyun-Joon Ha, Kyung Yeon Kang, and Won Koo Lee. "N-Methylative aziridine ring opening and asymmetric synthesis of MeBmt." Tetrahedron Letters 52, no. 45 (November 2011): 5918–20. http://dx.doi.org/10.1016/j.tetlet.2011.08.048.

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39

Franzyk, H., L. Ottesen, and J. Jaroszewski. "Ring Opening of a Resin-Bound Chiral Aziridine with Phenols." Synfacts 2010, no. 11 (October 21, 2010): 1319. http://dx.doi.org/10.1055/s-0030-1258826.

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40

Trocha, Aleksandra, Dorota G. Piotrowska, and Iwona E. Głowacka. "Synthesis of Enantiomerically Pure N-Boc-Protected 1,2,3-Triaminopropylphosphonates and 1,2-Diamino-3-Hydroxypropylphosphonates." Molecules 24, no. 21 (October 25, 2019): 3857. http://dx.doi.org/10.3390/molecules24213857.

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Abstract:

All possible isomers of 1,2,3-tri(N-tert-butoxycarbonylamino)propylphosphonate 6 were synthesized from the respective diethyl [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates 5 via opening the aziridine ring with trimethylsilyl azide (TMSN3) followed by hydrogenolysis in the presence of di-tert-butyl dicarbonate (Boc2O). [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates (1R,2R,1′S)-5a and (1S,2S,1′R)-5c were smoothly transformed into diethyl 3-acetoxy-1-benzylamino-2-[N-(1-phenylethyl)amino]propylphosphonates (1R,2R,1′S)-9a and (1S,2S,1′R)-9c, respectively by the opening of the aziridine ring with acetic acid. Transformations of [N-(1-phenylethyl)]-1-benzylamino-2,3-epiiminopropylphosphonates (1S,2R,1′S)-5b and (1R,2S,1′R)-5d into diethyl 3-acetoxy-1-benzylamino-2-[(1-phenylethyl)amino]propylphosphonates (1S,2R,1′S)-9b and (1R,2S,1′R)-9d were accompanied by the formation of ethyl {1-(N-benzylacetamido)-3-hydroxy-2-[(1-phenylethyl)amino]propyl}phosphonate (1S,2R,1′S)-10b and (1R,2S,1′R)-10d and 3-(N-benzylacetamido)-4-[N-(1-phenylethyl)]amino-1,2-oxaphospholane (3S,4R,1′S)-11b and (3R,4S,1′R)-11d as side products. Diethyl (1R,2R)-, (1S,2S)-, (1S,2R)- and (1R,2S)-3-acetoxy-1,2-di(N-tert-butoxycarbonylamino)propylphosphonates 7a–7d were obtained from the respective 3-acetoxy-1-benzylamino-2-[N-(1-phenylethyl)amino]propylphosphonates 9a–9d by hydrogenolysis in the presence of Boc2O.

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41

Hu, X. Eric. "Nucleophilic ring opening of aziridines." Tetrahedron 60, no. 12 (March 2004): 2701–43. http://dx.doi.org/10.1016/j.tet.2004.01.042.

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42

Stamm, Helmut. "Nucleophilic ring opening of aziridines." Journal für praktische Chemie 341, no. 4 (May 1999): 319–31. http://dx.doi.org/10.1002/(sici)1521-3897(199905)341:4<319::aid-prac319>3.0.co;2-9.

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43

Kim, Yongeun, Hyun-Joon Ha, Kyusung Han, Seung Whan Ko, Hoseop Yun, Hyo Jae Yoon, Min Sung Kim, and Won Koo Lee. "Preparation of 2,3-diaminopropionate from ring opening of aziridine-2-carboxylate." Tetrahedron Letters 46, no. 25 (June 2005): 4407–9. http://dx.doi.org/10.1016/j.tetlet.2005.04.039.

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44

Ottesen, Lars K., Jerzy W. Jaroszewski, and Henrik Franzyk. "Ring Opening of a Resin-Bound Chiral Aziridine with Phenol Nucleophiles." Journal of Organic Chemistry 75, no. 15 (August 6, 2010): 4983–91. http://dx.doi.org/10.1021/jo100505c.

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45

Seki, Kazutaka, Rongmin Yu, Yumi Yamazaki, Yasuhiro Yamashita, and Shū Kobayashi. "Asymmetric meso-aziridine ring-opening reactions using a chiral zirconium catalyst." Chemical Communications, no. 38 (2009): 5722. http://dx.doi.org/10.1039/b914271c.

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46

Diao, Tianning, Xiaoyu Sun, Renhua Fan, and Jie Wu. "Unexpected Ring-opening Reaction of Aziridine with Acetic Anhydride in DMF." Chemistry Letters 36, no. 5 (May 5, 2007): 604–5. http://dx.doi.org/10.1246/cl.2007.604.

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47

Baldwin, Jack E., Robert M. Adlington, Ian A. O'Neil, Christopher Schofield, Alan C. Spivey, and Joseph B. Sweeney. "The ring opening of aziridine-2-carboxylate esters with organometallic reagents." Journal of the Chemical Society, Chemical Communications, no. 23 (1989): 1852. http://dx.doi.org/10.1039/c39890001852.

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48

Golz, C., and C. Strohmann. "Crystal structure of [2-(triethylammonio)ethyl][(2,4,6-triisopropylphenyl)sulfonyl]amide tetrahydrate." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (April 30, 2015): 564–66. http://dx.doi.org/10.1107/s2056989015008105.

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Abstract:

The zwitterionic title compound, C23H42N2O2S·4H2O, crystallized as a tetrahydrate from a solution ofN-[(2,4,6-triisopropylphenyl)sulfonyl]aziridine in triethylamine, diethyl ether and pentane in the presence of moist air. It is formed by a nucleophillic ring-opening that is assumed to be reversible. The molecular structure shows a major disorder of the triisopropylphenyl group over two equally occupied locations. An interesting feature is the uncommon hydrate structure, exhibiting a tape-like motif which can be classified as a transition of the one-dimensional T4(2)6(2) motif into the two-dimensional L4(6)5(7)6(8) motif.

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49

Dauban, Philippe, and Robert H. Dodd. "2,3-Aziridino-2,3-dideoxy-d-ribono-γ-lactone 5-Phosphonate: Stereocontrolled Synthesis fromd-Lyxose and Unusual Aziridine Ring Opening." Journal of Organic Chemistry 62, no. 13 (June 1997): 4277–84. http://dx.doi.org/10.1021/jo9623494.

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50

Lee, Jaedeok, Jae Eun Lee, Hyun-Joon Ha, Se In Son, and Won Koo Lee. "N-Methylative aziridine ring opening: asymmetric synthesis of hygroline, pseudohygroline, and hygrine." Tetrahedron Letters 56, no. 6 (February 2015): 856–58. http://dx.doi.org/10.1016/j.tetlet.2014.12.133.

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