Cyclic guanidines. III. Synthesis of hypoglycemic 2-benzhydrylimino-1,3-diazacycloalkanes.

Abstract

2-Benzhydryliminoimidazolidine derivatives were prepared by the reactions of benzhydrylamines with 2-methylthio- or 2-chloro-2-imidazoline. The reaction of 1-benzhydryl-2-methylisothiourea or benzhydrylisocyanidedichloride with alkylenediamines gave the many 2-benzhydrylimino-1, 3-diazacycloalkanes (14-21). Compound 14, 15, and 17 were alkylated or acylated to give the ring nitrogen substituted derivatives. The alkyl or acyl derivatives of 2-benzhydryliminoimidazolidine obtained here have two tautomeric form, 2-amino and 2-imino form, which were discussed by use of the NMR spectral data. Some of 2-benzhydrylimino-1, 3-diazacycloalkanes showed hypoglycemic activity.