Reaction of N-(1-Phenylalkylidene)benzylamines with Benzoyl Cyanides

抄録

Reactions of various aldimines 4a-f with 4-nitrobenzoyl cyanide (2b) gave the Reissert-type compounds 5a-f. However, reaction of N-(1-phenylpropylidene)benzylamine (7a) with 2b gave 1-benzyl-4-hydroxy-5-imino-3-methyl-4-(4-nitrophenyl)-2-phenyl-4, 5-dihydropyrrole (8a). Similar reactions of 7b, 7c, and 12 with 2b gave the pyrrole derivatives 8b, 11, and 13, respectively. Next, the reaction of N-cyclohexylidenecyclohexylamine (14) with benzoyl cyanide (2a) was reexamined. The structure of the adduct 16 was different from that of the Reissert-type compound 15 described by Dornow and Lupfert.