A novel synthesis of methyl 1, 5-disubstituted imidazole-4-carboxylates using 3-bromo-2-isocyanoacrylates (BICA)

…, M Yamada, T Fukui, K Matsumoto

Index: Nunami; Yamada; Fukui; Matsumoto Journal of Organic Chemistry, 1994 ,  vol. 59,  # 25  p. 7635 - 7642

Full Text: HTML

Citation Number: 69

Abstract

Methyl l, &disubstituted imidazole-4-carboxylates 1 were synthesized using methyl 3- substituted 3-bromo-2-isocyanoacrylates 3 (BICA), and the reaction mechanism was elucidated. Reactions of 3, which were prepared by bromination of 3-substituted 2- (formy1amino) acrylates 6 followed by dehydration of the formylamino group, with a variety of primary amines gave imidazoles 1 in good overall yields. A mechanistic study ...