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Relevant bibliographies by topics / Aziridines

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Academic literature on the topic 'Aziridines'

Author: Grafiati

Published: 4 June 2021

Last updated: 30 November 2024

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Journal articles on the topic "Aziridines"

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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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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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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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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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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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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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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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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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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Dissertations / Theses on the topic "Aziridines"

1

Wells, Greggory M. "Synthesis and Biological Activity of N-Acyl Aziridines." Ohio University / OhioLINK, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1450458169.

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Díaz, de los Bernardos Sánchez Miriam. "New organocatalyzed transformations of aziridines." Doctoral thesis, Universitat Rovira i Virgili, 2013. http://hdl.handle.net/10803/284090.

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Entre los intermedios sintéticos más versátiles en química orgánica se encuentran las aziridinas, estos compuestos son heterociclos de tres miembros que presentan una funcionalidad amina. Un gran número de moléculas biológicamente activas contienen en su estructura estos anillos heterocíclicos de tres miembros. En este contexto, la transformación selectiva de aziridinas ha generado un creciente interés en la comunidad sintética hacia la síntesis de diversos aminoácidos, productos naturales y compuestos biológicamente activos. Actualmente, la organocatálisis representa un área emergente de metodología orgánica y puede definirse como una forma de catálisis en la que moléculas orgánicas actúan como catalizadores, permitiendo llevar a cabo procesos en ausencia de metal. El presente trabajo tiene como objetivo desarrollar nuevas estrategias sintéticas en la transformación de aziridinas mediante catálisis selectiva basada en moléculas orgánicas, centrándose en desarrollar nuevas aplicaciones sintéticas para estos versátiles intermedios.
Aziridines are among the most versatile intermediates in organic synthesis. A number of biologically significant molecules contain these strained threemembered rings within their structures. Consequently, there is currently a growing interest of the synthetic community in selective transformations of aziridines. This thesis aims at the development of new synthetic strategies for efficient aziridine transformations using selective catalysis based on small organic molecules. Thus, new organocatalytic procedures in aziridine ring-opening chemistry, focusing on the development of efficient synthetic applications of these versatile intermediates were envisioned.

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Zeytinci, Serhat. "Synthesis Of Ferrocenyl Substituted Aziridines." Master's thesis, METU, 2006. http://etd.lib.metu.edu.tr/upload/12607285/index.pdf.

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A new method for the efficient synthesis of ferrocenylenones was developed. Acryloyl, methacryloyl, crotonyl, cinnamoyl, and &
#946
-methylcrotonyl chlorides reacted with ferrocene in the presence of a Lewis acid (EtAlCl2 or EtAlCl2-Me3Al) to give the corrosponding ferrocenylenones (acryloyl, methacryloyl, crotonyl, cinnamoyl, and &
#946
-methylcrotonylferrocenes) in good isolated yields. Using the Gabriel-Cromwell reaction, acryloyl and crotonoylferrocenes were converted to the novel ferrocenyl substituted aziridines with benzylamine, isopropylamine and furfurylamine. The aziridines were isolated in good to excellent yields.

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Alezra, Valérie. "Nouvelles voies d'accés à des sérines alpha-substituées énantiopures à partir d'aziridino-esters ou d'oxazolidino-esters." Paris 5, 2000. http://www.theses.fr/2000PA05P614.

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Kloesges, Johannes. "Novel Chemistry of aziridines and azetidines." Thesis, University of Oxford, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.509969.

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Rosser, Clare M. "Synthesis and desymmetrisation of meso aziridines." Thesis, University of York, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.399251.

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Cantrill, Alexander A. "Synthetic studies of N-diphenylphosphinyl aziridines." Thesis, University of Bristol, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.243672.

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8

Nakai, Kazuo. "Reactivities and Applications of Chiral Activated Aziridines." 京都大学 (Kyoto University), 1998. http://hdl.handle.net/2433/182477.

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Sweeney, J. B. "New synthetic methods with allylstannanes and aziridines." Thesis, University of Oxford, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.382654.

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Humphreys, Philip G. "New reactions of Î±-lithiated terminal aziridines." Thesis, University of Oxford, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.442451.

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Books on the topic "Aziridines"

1

K, Yudin Andrei, ed. Aziridines and epoxides in organic synthesis. Weinheim: Wiley, 2006.

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Lusthof, Klaas Jurjen. Potential antitumor bis(aziridinyl)benzoquinones and DNA: Alkylation and redox cycling = Potentiële bis(aziridinyl) benzochinoncytostatica en DNA : alkylering en redox cycling. [s.l.]: [s.n.], 1990.

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3

Roser, Joachim. Synthese und Thermolyse von Eninyl-Oxiranen, Eninyl-Aziridinen und Eninyl-Nitronen: Siebengliedrige Cycloallen-Zwischenstufen durch 1,7-dipolare Elektrocyclisierung ; ein neuer Weg zu Derivaten des Furans, Pyrrols und [alpha]-Pyridons. [s.l.]: [s.n.], 1987.

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4

Chen, Gang Greg. Synthetic applications of functionalized aziridines. 2007.

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Yudin, Andrei K., ed. Aziridines and Epoxides in Organic Synthesis. Wiley, 2006. http://dx.doi.org/10.1002/3527607862.

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Yudin, Andrei K. Aziridines and Epoxides in Organic Synthesis. Wiley & Sons, Incorporated, John, 2006.

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Yudin, Andrei K. Aziridines and Epoxides in Organic Synthesis. Wiley-VCH, 2006.

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Yudin, Andrei K. Aziridines and Epoxides in Organic Synthesis. Wiley & Sons, Limited, John, 2006.

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9

Synthesis of Aziridines and Oxaziridines from Imines. Elsevier, 2024.

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Dermer, O. Ethylenimine and Other Aziridines: Chemistry and Applications. Elsevier Science & Technology Books, 2012.

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Book chapters on the topic "Aziridines"

1

Deyrup, James A. "Aziridines." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 1–214. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187180.ch1.

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Fanta, Paul E. "Aziridines." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 524–75. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470239704.ch2.

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Sweeney, Joseph B. "Synthesis of Aziridines." In Aziridines and Epoxides in Organic Synthesis, 117–44. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607862.ch4.

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Botuha, Candice, Fabrice Chemla, Franck Ferreira, and Alejandro Pérez-Luna. "Aziridines in Natural Product Synthesis." In Heterocycles in Natural Product Synthesis, 1–39. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634880.ch1.

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Fokin, Valery V., and Peng Wu. "Epoxides and Aziridines in Click Chemistry." In Aziridines and Epoxides in Organic Synthesis, 443–77. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607862.ch12.

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Hodgson, David M., and Christopher D. Bray. "Metalated Epoxides and Aziridines in Synthesis." In Aziridines and Epoxides in Organic Synthesis, 145–84. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607862.ch5.

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Aggarwal, Varinder K., D. Michael Badine, and Vijayalakshmi A. Moorthie. "Asymmetric Synthesis of Epoxides and Aziridines from Aldehydes and Imines." In Aziridines and Epoxides in Organic Synthesis, 1–35. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607862.ch1.

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Grüschow, Sabine, and David H. Sherman. "The Biosynthesis of Epoxides." In Aziridines and Epoxides in Organic Synthesis, 349–98. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607862.ch10.

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Lowden, Philip A. S. "Aziridine Natural Products - Discovery, Biological Activity and Biosynthesis." In Aziridines and Epoxides in Organic Synthesis, 399–442. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607862.ch11.

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Ohno, Hiroaki. "Vinylaziridines in Organic Synthesis." In Aziridines and Epoxides in Organic Synthesis, 37–71. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2006. http://dx.doi.org/10.1002/3527607862.ch2.

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Conference papers on the topic "Aziridines"

1

D’hooghe, Matthias, and Norbert De Kimpe. "Highly Regioselective Synthesis of Functionalized Aminonitriles Starting from 2-(w-cyanoalkyl)aziridines." In The 12th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2008. http://dx.doi.org/10.3390/ecsoc-12-01230.

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D’Hooghe, Matthias, and Norbert De Kimpe. "Reactivity of 1-arenesulfonyl- and 1-alkyl-2-(bromomethyl)aziridines towards Lithium Cuprate Reagents." In The 9th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01474.

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Fortunato, Milene, Filipa Siopa, and Carlos Afonso. "A new home-made UV reactor for scale-up production of α-hydroxycyclopenteno-aziridines." In 7th International Electronic Conference on Medicinal Chemistry. Basel, Switzerland: MDPI, 2021. http://dx.doi.org/10.3390/ecmc2021-11558.

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Monteiro, Mariana Crespo, Carlos A. M. Afonso, and Filipa Siopa. "Pd-Catalyzed Cycloaddition of Bicyclic Aziridine with Isocyanates." In ECMC 2022. Basel Switzerland: MDPI, 2022. http://dx.doi.org/10.3390/ecmc2022-13424.

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Keppler, Karen, Jürgen Stohner, Martin Quack, Carine Manca Tanner, and Sieghard Albert. "HIGH RESOLUTION INFRARED SPECTROSCOPY OF AZIRIDINE-2-CARBONITRILE (C3H4N2)." In 2022 International Symposium on Molecular Spectroscopy. Urbana, Illinois: University of Illinois at Urbana-Champaign, 2022. http://dx.doi.org/10.15278/isms.2022.te01.

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Montaos, Marco, Eduardo Fernàndez-Megîa, and Celia Penide. "Enantiospecific, Stereoselective Synthesis of Enantiomerically Pure Aziridine-2-carboxylic Acids from Aspartic Acid." In The 2nd International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1998. http://dx.doi.org/10.3390/ecsoc-2-01673.

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Yeh, Wei-Ming, Richard A. Lawson, Laren M. Tolbert, and Clifford L. Henderson. "Application of aziridine reactive rinses in a post-development process to reduce photoresist pattern collapse." In SPIE Advanced Lithography, edited by Mark H. Somervell and Thomas I. Wallow. SPIE, 2012. http://dx.doi.org/10.1117/12.928877.

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Usman, Muhammad, Muhammad Akbar, Taswar Ahsan, and Muhammad Hamza. "Extraction and Identification of Aziridine Derivatives in VOCs from Pleurotus ostreatus: Impact on Plant Pathogens." In The 3rd International Electronic Conference on Agronomy. Basel Switzerland: MDPI, 2023. http://dx.doi.org/10.3390/iecag2023-16378.

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Braga, Antonio Luiz, Syed M. Salman, Sayyar Muhamamd, Oscar E. D. Rodrigues, Luciano Dornelles, and Ricardo S. Schwab. "Copper Oxide Nanoparticles-Catalyzed Aziridine Ring Opening with Diaryl Diselenides Under Ionic Liquid as Reaction Medium." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0026-1.

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Marin-Luna, Marta, Javier Diaz-Moreno, Angel Vidal, and Mateo Alajarin. "Unexpected Transformatios of Aziridino-Heterocumulenes Built on Ortho-Benzene Scaffolds." In The 18th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2014. http://dx.doi.org/10.3390/ecsoc-18-a043.

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Reports on the topic "Aziridines"

1

Guo, Yin, Angela K. Wilson, Cary F. Chabalowski, and Donald L. Thompson. A Semiclassical Study of Tunneling Effects in Aziridine. Fort Belvoir, VA: Defense Technical Information Center, November 1999. http://dx.doi.org/10.21236/ada370928.

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