Novel Mitomycin C Amidines: Synthesis and Their Reactions with Amines

Article abstract of DOI:10.1021/jo00234a017

Reactions of formamide acetals (e.g.DMFDMA, 10, 12) with mitomycin C (1) has afforded novel amidine derivatives (e.g. 7-9, 11, 13).Investigation of reactions of amines with bisamidine 8 in both polar and nonpolar solvents (e.g.MeOH vs CHCl3) has led to the discovery that 8, in its reactions with primary amines in methanol, behaves as a mitomycin A (2) equivalent to afford 7-N-substituted mitosanes (e.g. 16-19).In contrast, bisamidine 8 undergoes a selective deamidination reaction with primary amines in chloroform to afford monoamidine 14.