Regioselectivity of the hydrolysis of 2-(1-alkoxyvinyl)-substituted imidazolidines, 1, 3-thiazolidines, and 1, 3-oxazolidines

NA Keiko, EA Funtikova, NV Vchislo, LI Larina…

Index: Keiko; Funtikova; Vchislo; Larina; Frolov Russian Journal of Organic Chemistry, 2011 , vol. 47, # 12 p. 1832 - 1840

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Abstract

Abstract 2-(1-Alkoxyvinyl)-1, 3-thiazolidines reacted with H 2 O or D 2 O in the presence of 105 mol% of p-toluenesulfonic acid or trifluoroacetic acid (20° C, 1 h) to give 2-acetyl-1, 3- thiazolidine in quantitative yield. 2-(1-Alkoxyvinyl)-3, 5-diphenylimidazolidines underwent hydrolysis in the presence of 20 mol% of an acid (20° C, 24 h) at the vinyloxy group with high regioselectivity yielding 2-acetylimidazolidines. Hydrolysis of 2-(1-alkoxyvinyl)-3- ...