Helvetica Chimica Acta p. 1732 - 1736 (1987)
Update date:2022-07-29
Topics:
Trifonov, Latchezar S.
Orahovats, Alexander S.
The intramolecular Diels-Alder reaction conducted with acetylenic acylureas, obtained from carbodiimides, and the acetylenic acid 5 and its derivatives 13 gave the 1,2-annellated barrelene 14 (from 13a) and the benzobarrelenes 8 (from 5) and 15 (from 13b); in the case of 3-butyinoic acid (1), <1,3>-H shifts were observed.The formation of the azabarrelenes 16 (from 13c) as an intermediate is postulated which looses HCN to afford the indolinone 17.The acylureas 6 and 9 underwent isocyanate cleavage instead of <4 + 2> cyclization.
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