L. Somogyi
Jun 13, 1994
Citations
0
Influential Citations
5
Citations
Journal
European Journal of Organic Chemistry
Abstract
The synthesis of 3-acetylcoumarin (thio)acylhydrazones 1a–e and their transformation to 5-substituted 3-acetyl-2-(3-coumarinyl)-2-methyl-1,3,4-oxa(thia)diazolines 2a–f (cyclic isomers of the alternatively accessible diacylhydrazones, e.g. 1f–h) under acetylating conditions are described. Treatment of the acetylation products 2c–f with the acetylating agent Ac2O/ZnCl2 resulted in the unexpected formation of acylhydrazones 1c, d, i with cleavage of the oxadiazoline ring and simultaneous loss of the acetyl group.