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Cycloaddition of Carbodiimides with a Heteroaromatic Substituent to Allenic Acids

✍ Scribed by Latchezar S. Trifonov; Nadja I. Christova; Valentin S. Dimitrov; Alexander S. Orahovats

Publisher: John Wiley and Sons
Year: 1992
Tongue: German
Weight: 227 KB
Volume: 75
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19920750426

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✦ Synopsis

Cycloaddition of the allenic acid 3 with the N-cyclohexyl-N'-heteroaromatic carbodiimides 2a and 2b gave the isomeric pyrido[l,2-~]pyrimidinones 4 and 5 and thiazolo[3,2-~]pyrimidinones 6 and 7, respectively, instead of the expected Diels-Alder adducts analogous to 1. The compounds of the latter type, i.e. 8 and 9, were formed from 3 and carbodiimides 2c and 2d, respectively, containing an N'-(pyrazin-2-yl) or N'-(pyrimidin-Zyl) substituent.

') A preliminary account of some results was given at the '2nd International IUPAC Symposium on Organic Chemistry: Technological Perspectives', Baden-Baden, FRG, 199 1.

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