Reactions of 1,4-NCCN-, 1,4-NNCN- and 1,5-NCCCN-binucleophiles with dicarboxylic acids cyclic anhydrides as a method of heterocyclic compounds synthesis (a review)

Abstract

Critical analysis of published information related to the features of reaction of 1,4-NCCN-, 1,4-NNCN and 1,5-NCCCN-binucleophiles with cyclic anhydrides of dicarboxylic acids has been presented in the review. It has been shown that the reaction of named anhydrides with 1,4-NCCN-binucleophiles leads to the formation of the imidazole fragment that contains carboxyl-containing moiety. It has been shown that benzimidazole derivatives are among the most studied products of reaction between 1,4-NCCN- and cyclic anhydrides of dicarboxylic acids due to the high availability of initial compounds. The approaches to chemical modification of latter compounds have been discussed as well. It has been found out that 1,4-NNCN-binucleophiles used in reactions with cyclic anhydrides of dicarboxylic acids are mostly presented by amidines and amidrazones. The effects of structures of initial compounds and conditions of reactions on the products of reaction have been described. Literature data shows that the reaction of 1,5-NCCCN-binucleophiles such as amides and hydrazides of anthranilic acid, diamino-substituted polycyclic arenes and 2-azaheterylanilines with cyclic anhydrides of dicarboxylic acids commonly results in the formation of pyrimidine derivatives. It has been established that the application of cyclic anhydrides of non-symmetric dicarboxylic acid as reagents may cause the ambiguity of the reaction pathways. However, the formation of single products of interaction between binucleophiles and non-symmetric anhydrides can be achieved by variation of reaction conditions. The biological activity of the discussed reaction products has been considered in detail. It has been shown that the above-mentioned compounds reveal antibacterial, antifungal, anticancer, immunomodulate, and antidiabetic activities.