Synthesis of 1,5,3,7-Diazadiphosphocine-1,5-dicarboxylic Acids and Their Esterifications

Abstract

In order to synthesize new bioactive compounds and contrasting agents, reactions of glycine and glutamic acid with paraformaldehyde and hypophosphorous acid were executed. Products are 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-diacetic acid (4a), 2-[5- (1,2-dicarboxyethyl)-3,7-dihydroxy-3,7-dioxo-315.715-[1,5,3,7]-diazadiphosphocan-1-yl]-succinic acid (4b) and 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-di-(2-glutaric acid) (4c). Esterification of 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphos-phocine- 1,5-diacetic acid (4a) by treatment of methanol, ethanol and propanol were executed. 3,7- Dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-diacetic acid methyl ester (5a), 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphosphocine-1,5-diacetic acid ethyl ester (5b) and 3,7-dihydroxy-3,7-dioxoperhydro-1,5,3,7-diazadiphospho-cine-1,5-diacetic acid propyl ester (5c) were, respectively synthesized in good yields. In case of 3,7-dihydroxy-3,7-dioxoperhydro- 1,5,3,7-diaza-diphosphocine-1,5-di-(2-glutaric acid) (4c) by treatment of methanol, yielded 2- [5-(1,2-dicarboxyethyl)-3,7-dihydroxy-3,7-dioxo-315.715-[1,5,3,7]diazadiphosphocan-1-yl]- succinic acid methyl ester (5d).