Reactions with 4,5-DI (p-Chlorophenyl)Imidazolidine-2-Thione

Abstract

Alkylation of 1 gave the S-alkyl derivatives 3a-c. The S-methyl derivative 3a reacted with amines, with the elimination of methanethiol, to give the 2-amino derivatives 4a-c; with thiosemicarbazide to yield the imidazo [2,1-c]s-triazole 6; and with anthranilic acids to yield the imidazo[2,1-b]quinazolines 8a, b. Compound 3a reacted also with active-methylene compounds to give the ketene aminals 10a-c. Alkylation of 1 with dihaloalkanes afforded the bis compounds 14a, b. In the case of 1,2-dibromoethane, the imidazo[2,1-b]thiazole 13 was obtained. The reaction of 1 with α-halo-ketones led directly to the imidazo[2,1-b]thiazoles 15a-c and 17. However, with halo-acetoacetanilides, the acyclic intermediates 20d-g were isolated.

Key Words:

• Alkylation
• ketene aminals
• imidazo heterocycles