Cycloaddition of unactivated 2-aza-1,3-dienes with heterocumulenes: a convenient route to the synthesis of 1,3-difunctionalized compounds
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1739-1744
- https://doi.org/10.1039/p19880001739
Abstract
The cycloaddition of unactivated 2-aza-1,3-dienes (2) with isocyanates and isothiocyanates (3) gives with complete regio- and chemo-selectivity 1,2-dihydropyrimidin-4(3H)-ones and -thiones (4). This is the first example of a cycloaddition of unactivated 2-aza-1,3-dienes with heterocumulenes. Enamino amides and thioamides (5) were obtained by reduction with LiAIH4of (4). Also, 3-oxoamides and 3-oxothioamides (6) were prepared by acid hydrolysis of compound (4) or (5).Keywords
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