Regioselectivity of the hydrolysis of 2-(1-alkoxyvinyl)-substituted imidazolidines, 1,3-thiazolidines,and 1,3-oxazolidines |
| |
Authors: | N A Keiko E A Funtikova N V Vchislo L I Larina Yu L Frolov |
| |
Institution: | 1.Favorskii Irkutsk Institute of Chemistry, Siberian Division,Russian Academy of Sciences,Irkutsk,Russia;2.Irkutsk National State Research Technical University,Irkutsk,Russia |
| |
Abstract: | 2-(1-Alkoxyvinyl)-1,3-thiazolidines reacted with H2O or D2O 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-phenyl-1,3-oxazolidines in the presence of 10 mol % of
p-toluenesulfonic acid (20°C, 5 days) takes two pathways, one of which involves the endocyclic C-O bond with ring opening and
the other involves the vinyloxy group to produce 2-acetyl-3-phenyl-1,3-oxazolidine. Unlike phenyl-substituted 1,3-thiazolidines
and imidazolidines, hydrolysis of their 3-methyl- and 3,5-dimethyl-substituted analogs in acid medium occurs mainly via ring
opening. The observed hydrolysis pathways were interpreted in terms of B3PW91/6-311G(d,p) quantum-chemical calculations. |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|