2 edition of chemistry of non-activated aziridines: Synthesis and reactivity. found in the catalog.
chemistry of non-activated aziridines: Synthesis and reactivity.
Iain David Glean Watson
Written in English
The reactivity of the synthesized non-activated aziridines was examined. Non-activated aziridines were found to be reactive to a number of different nucleophiles. In particular, the ring opening reactions of non-activated aziridines with amine nucleophiles was efficiently catalyzed by tris-(pentafluorophenyl)borane leading to derivatives of trans-1,2-diamines in high yields. A mechanistic investigation of the reaction suggests that in situ formed [(C 6F5)3B(OH2)]·H2O catalyses the opening through a Brensted acid manifold. Conversion of allyl aziridines into alpha-aziridino aldehydes creates reactive intermediates that react with nucleophiles without destruction of the aziridine ring. The conversion from allyl aziridines takes advantage of the high enantioselectivities and unique regioselectivities achieved by the palladium catalyzed process. Finally, the application of non-activated aziridines towards the synthesis of a number of radiolabelled beta-adrenergic agonists and antagonists was undertaken, providing a concrete example of the usefulness of aziridines as reactive intermediates in organic synthesis.*Investigations into the synthesis and reactivity of non-activated aziridines were undertaken.1 New synthetic methodologies for the synthesis of non-activated aziridines were developed by the N-functionalization of NH-aziridines. In particular, the palladium-catalyzed allylic amination of N-unsubstituted aziridines has been carried out. The use of NH aziridines as nucleophiles favors formation of branched products in the case of aliphatic allyl acetates. The regioselectivity of this reaction is opposite to that observed when other amines are used as nucleophiles. These studies provide evidence for the palladium-catalyzed isomerization of the branched (kinetic) product formed with common secondary amines into the thermodynamic (linear) product. On the contrary, the branched allyl products obtained from N-unsubstituted aziridines do not undergo the isomerization process. The methodology addresses the important issue of forming quaternary carbon centers next to nitrogen. The new insights into the mechanism of palladium-catalyzed allylic amination obtained will facilitate the synthesis of complex heterocycles and the design of new ligands to control branched/linear ratio as well as absolute stereochemistry of allyl amines.1 (a) Watson, I. D. G.; Yu, L.; Yudin, A. K. Advances in nitrogen transfer reactions involving aziridines. Acc. Chem. Res. 2006, 39, 194-206. (b) Watson, I. D. G.; Yudin, A. K. New insights into the mechanism of palladium-catalyzed allylic amination. J. Am. Chem. Soc. 2005, 127, 17516 - 17529. (c) Watson, I. D. G.; Styler, S. A.; Yudin, A. K. Unusual selectivity of unprotected aziridines in palladium-catalyzed allylic amination enables facile preparation of branched aziridines. J. Am. Chem. Soc. 2004, 126, 5086-5087. (d) Watson, I. D. G.; Yudin, A. K. Ring-opening reactions of nonactivated aziridines catalyzed by tris(pentafluorophenyl)borane. J. Org. Chem. 2003, 68, 5160-5167. (e) Watson, I. D. G.; Yudin, A. K. Selective functionalization of small organic molecules using electrophilic nitrogen sources. Curr. Opin. Drug Discovery Dev. 2002, 5, 906-917. *Please refer to dissertation for diagrams.
|The Physical Object|
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The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The chemistry of heteroatom substituted aziridines opens up fascinating questions of reactivity and stability We have been interested in the preparation of iodoaziridines as a novel functional group that offers the potential to provide precursors to a wide range of derivatives with complementary reactivity to existing aziridine.
Kurzbeschreibung. This clearly structured book presents the much-needed information about aziridines and epoxides in a compact and concise way. The renowned editor has succeeded in gathering together excellent authors to cover in equal depth synthesis, applications and the biological aspects. IV. Reactivity of activated aziridines and azetidines • Non-activated aziridine reactivity using donor-acceptor activated aziridines: • Reaction with electron-rich alkene: L. Li, X. Wu, J. Zhang, Chem. Commun. , 47,
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Aziridines are the smallest saturated nitrogen-containing heterocycles. Azirines have the same three-membered ring, but with one double bond. These are of two types: 1 H-azirines and ed to their open-chain amino analogues, these compounds exhibit increased reactivity towards nucleophiles thanks to the high ring strain of the three-membered ring.
This review systematically describes the synthesis and reactions of epoxides and aziridines using organocatalysis, and includes their reactions like desymmetrization, regioselective nucleophilic ring-opening and cycloaddition with CO on the various generic modes of activation of organocatalysis, a systematic classification of organocatalysts used for regioselective nucleophilic ring Cited by: 9 AZIRIDINES: RETHINKING THEIR APPLICATION AND MANIPULATION IN SYNTHESIS Christopher R.
Butler Septem INTRODUCTION Aziridines (1) have been synthetic targets as well as useful building blocks in synthesis since Gabriel’s discovery of the smallest nitrogen containing heterocycle.1,2 Attracted by the increased strain and unique reactivity of the three-membered ring.
ChemInform Abstract: Synthesis and Reactivity of Non-Activated 2-(Chloromethyl)aziridines. Article in ChemInform 52(35) December with 17 Reads How we measure 'reads'. Summary This chapter summarizes the following epoxides and aziridines: Corey‐Chaykovsky reaction; Darzens glycidic ester condensation; Hoch‐Campbell aziridine synthesis; Jacobsen‐Katsuki epoxidatio.
Baran Lab Aziridines in S ynthesis M. Jessing 1 N R Activated aziridines R = CO2R, SO2R and COR Non-activated aziridines R = H, Alkyl and Aryl HO NH2 Chemistry of non-activated aziridines: Synthesis and reactivity. book SO NH 2 O O N H Aziridines can be synthesized in numerous ways including SN2 displacement, addition, addition of carbenes, electrophiles, nitrenes and reduction H.
Wenker. JACS. Non-activated aziridines as building blocks for the synthesis of aza-heterocycles (microreview). Ring-opening reaction of aziridines with amines under the influence of dimethyl sulfoxide. Tetrahedron Letters57 Synthesis of aziridines by visible-light induced decarboxylative cyclization of N-aryl glycines and diazo compounds.
Aziridines represent a valuable class of strained compounds in azaheterocyclic chemistry with diverse synthetic and biological applications.
1 The interest in aziridines as synthons in organic chemistry is due to the general influence of ring strain on chemical reactivity, making them important building blocks for the preparation of a large variety of ring-opened and ring-expanded.
Abstract. Functionalized aziridines, especially aziridinecarboxylic esters, are highly valuable small-ring heterocycles for the synthesis of a large variety of anomalous amino acids, new types of ligands for catalytic purposes, new synthons, and four- and five-membered ring heterocycles through ring expansion reactions.
trans- and cisAlkylarylchloroazetidinones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were transformed into the corresponding non-activated trans- and cisaryl(hydroxymethyl)aziridines via reductive ring contraction using LiAlH 4 in Et 2 rmore, transaryl(hydroxymethyl)aziridines were.
Aziridines and epoxides are among the most widely used intermediates in organic synthesis, acting as precursors to complex molecules due to the strains incorporated in their skeletons.
Besides their importance as reactive intermediates, many biologically active compounds also contain these three-membered rings.
Filling a gap in the literature, this clearly structured book presents the much. Martin A. Lowe, Mehrnoosh Ostovar, Serena Ferrini, C. Chun Chen, Paul G. Lawrence, Francesco Fontana, Andrew A. Calabrese, Varinder K. Aggarwal, Palladium‐Mediated Annulation of Vinyl Aziridines with Michael Acceptors: Stereocontrolled Synthesis of Substituted Pyrrolidines and Its Application in a Formal Synthesis of (−)‐α‐Kainic Acid.
Aziridines, as three-membered rings, posses inherent ring strain that makes them important building blocks in organic chemistry 1. They display a vast array of reactivity often involving aziridine ring opening 2,3, particularly as intermediates in the synthesis of functionalized amines 4,5, or the formation of other nitrogen containing.
Saturated azacyclopropane compounds. They include compounds with substitutions on CARBON or NITROGEN atoms. | Explore the latest full-text research PDFs. Jevgeņija Lugiņina, Māris Turks, Non-activated aziridines as building blocks for the synthesis of aza-heterocycles (microreview), Chemistry of Heterocyclic Compounds, /sz, 52, 10, (), ().
Reactivity and regioselectivity in the ring opening of 2-substituted non-activated aziridines: A density functional theory based analysis. Computational and Theoretical Chemistry, DOI: / Vittorio Pace, Laura Castoldi, Wolfgang Holzer.
The synthesis and reactivity of aziridines have been reviewed from time to time. 2,3 Some review articles focusing on specific type of aziridines such as aziridinecarboxylates, 4 2-haloaziridines, 5 2-methyleneaziridines, 6 and 2-vinylaziridines 7,8 have been.
Title:An Updated Library on the Synthesis of Aziridines VOLUME: 6 ISSUE: 3 Author(s):Anindita Mukherjee, Nirnita C. Ghosal, Grigory V. Zyryanov, Adinath Majee* and Sougata Santra* Affiliation:Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Str., K-2, Yekaterinburg,Department of Chemistry, University of.
HETEROCYCLIC CHEMISTRY BOOK FREE PDF DOWNLOAD Reactions and Synthesis Reactions with Electrophilic Reagents Addition to Nitrogen Ring synthesis Aziridines and Azirines Azetidines and β-Lactams Pyrrolidines Reactions Corey-Chaykovsky Reaction De Kimpe Aziridine Synthesis Prilezhaev Reaction Sharpless Direct Aza-Darzens Synthesis of N-Alkyl cis-Aziridines A.
System for the Synthesis of cis-Aziridine Carboxylates J. Aziridines and epoxides are among the most widely used intermediates in organic synthesis, acting as precursors to complex molecules due to the strains incorporated in their skeletons.
Besides their importance as reactive intermediates, many biologically active compounds also contain these three-membered rings. This chapter focuses on the importance of aziridinium ions as intermediates in organic chemistry.
The principal aim is to gain insight into the factors to take into account for the selective synthesis of a variety of functionalized amines via aziridinium salts, such as the nature of the aziridinium ion (ring strain and N- and C-substituents of the aziridine ring), the nucleophile, and the.Reactivity of Monocyclic Aziridines Aziridines have attracted considerable attention as starting materials in numerous applications, and many papers and review articles dealing with the synthesis of aziridines as well as their use in synthetic applications.