The Journal of Organic Chemistry

The cyclization of N-alkenylthionamides to thiazolines and dihydrothiazines

PAS SMITH, JM SULLIVAN

Index: Smith,P.A.S.; Sullivan,J.M. Journal of Organic Chemistry, 1961 , vol. 26, p. 1132 - 1136

Full Text: HTML

Citation Number: 12

Abstract

A group of N-alkenylbenzthionamides and acetthionamides have been prepared from the corresponding isothiocyanates and Grignard reagents. Allylic N-alkenylthionamides cyclize when treated with acidic catalysts such as aluminum chloride, but not with benzoyl peroxide. The position of cyclization follows the Markovnikov rule with an apparent slight preference for thiazoliies over dihydrothiazines when other factors are equal.