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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Three-Membered Azaheterocycles Based on α , β-Unsaturated Ketones

Author(s): V. A. Chebanov, A. I. Zbruyev, S. M. Desenko, V. D. Orlov and F. G. Yaremenko

Volume 12, Issue 10, 2008

Page: [792 - 812] Pages: 21

DOI: 10.2174/138527208784911888

Price: $65


The present review is devoted to heterocyclizations of α,β-unsaturated carbonyl compounds which result in the formation of three-membered partially hydrogenated nitrogen containing heterocyclic systems – aziridinyl ketones, biand tricyclic aziridines. Scientists are interested in these classes of heterocyclic compounds first of all by their photochromic properties and high sensitivity towards UV-VIS irradiation. From the other hand, these compounds are interesting from the viewpoint of classical problems of organic chemistry, among them reactivity, chemo- and regio-selectivity, stereochemistry and many other. The main aim of the publication is a comprehensive review and organization of the known literature data devoted to the reactions of α,β-unsaturated ketone derivatives utilized in the synthesis of aziridines and their chemical and photochemical properties. The first part of the review deals with synthesis and chemical properties of aziridinyl ketones. Two main groups of the reactions leading to target compounds – one-pot synthesis directly from unsaturated carbonyl compounds and step-by-step pathway including their initial modification – are described as well as chemical transformation of azyridinyl ketones. In the second section several synthetic pathways to bi- and tricyclic aziridines like dihyrdoazireno[1,2-c]imidazoles, tetrahydroazireno[ 1,2-a]pyrazines and dihydroazireno[1,2-a]quinoxalines are described and some aspects of stereo- and regoselectivity of appropriate reactions are discussed. The last part of the review is concerned with chemical behavior of aziridinyl aniles in numerous organic reactions including photochemical transformations, cycloadditions, rearrangements, cross-couplings and other. Stereochemistry of such processes and their mechanisms are touched as well.

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