Article ID Journal Published Year Pages File Type
5279543 Tetrahedron Letters 2005 5 Pages PDF
Abstract

Without additional reagents, the Baylis-Hillman acetates 2 underwent nucleophilic substitution reaction with imidazole readily in aqueous THF solution to afford the corresponding N-substituted imidazole derivatives 3 in good to excellent yields. Moreover, the reaction between the in situ generated DABCO salt of Baylis-Hillman acetates 4 and imidazole occurs in aqueous THF providing the SN2 type products 5. The simpler operational procedure, better stereoselectivity and higher efficiency over conventional method make the present protocol practical for the preparation of imidazole derivatives.

Graphical abstractWithout additional reagents, the Baylis-Hillman acetates 2 underwent nucleophilic substitution reaction with imidazole readily in aqueous THF solution to afford the corresponding N-substituted imidazole derivatives 3 in good to excellent yields. Moreover, the reaction between the in situ generated DABCO salt of Baylis-Hillman acetates 4 and imidazole occurs in aqueous THF providing the SN2 type products 5. The simpler operational procedure, better stereoselectivity, and higher efficiency over conventional methods make the present protocol practical for the preparation of imidazole derivatives.Download full-size image

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
Authors
, , ,