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Amino-α,β-unsaturated ethylenic and acetylenic carbonyl compounds as synthons for the assembly of heterocycles (review)

✍ Scribed by I. A. Maretina; G. V. Asratyan; N. G. Ostroumov

Book ID: 104781792
Publisher: Springer US
Year: 1992
Tongue: English
Weight: 635 KB
Volume: 28
Category: Article
ISSN: 0009-3122
DOI: 10.1007/bf00474481

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✦ Synopsis

The reactivity of en-and ynaminocarbonyl compounds towards two-center reactants to give five-and sevenmembered heterocycles with two heteroatoms, and condensed rings, is reviewed. The behavior of these systems towards 1,3-dipolar cycloaddition is noted.

Interest has recently developed in the chemistry of conjugated en-and ynamines as starting materials for the synthesis of heterocycles.

The first reports on the preparation of enaminocarbonyl compounds ((I-III)R2NCH--CHCOX X = H (I, IV), R 1 (II, V), OR 1 (III, VI)) appeared in the 1860's, and their chemical behavior has been examined intensively since the 1920's, being the subject of several reviews [1-4] including some recent ones [5, 61.

Acetylenic aminocarbonyl compounds R2NC -= CCOX (IV-VI) were not synthesized for a century after their ethylenic analogs [7]. This group of compounds has received much less attention, and only a few representatives have been obtained.

The present review seeks to systematize, generalize, and compare the chemistry ofen-and ynaminocarbonyl compounds as synthons for the guided preparation of heterocycles.

The question of the structure of an c~ isomerism in enaminocarbonyl compounds has been closely studied [1, p. 52; 8-221.

Three forms are theoretically possible, namely the enaminoketone (A), ynaminoenol (B), and iminoketone (C):

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