Synthesis and reactivity of 3-(2,2-dimethylhydrazono)-5-R-cyclopentane-1,1,2,2-tetracarbonitriles

A new method of the synthesis of 3-(2,2-dimethylhydrazono)-5-R-1,1,2,2-tetracarbonitriles via oxidation of 3-(2,2-dimethylhydrazino)-5-R-1,1,2,2- tetracarbonitriles with diluted nitric acid was developed. High reactivity of 3-(2,2-dimethylhydrazono)-5-R-1,1,2,2-tetracarbonitriles caused by the presence of ethyl-1,1,2,2-tetracarbonitrile and N,N-dimethylhydrazone moieties allowed obtaining 2-methyl-5-R-3,4-dihydro-2H-cyclopenta[e]1,2,4triazine-6,6,7,7-tetracarbonitriles, 3-amino-4-(2,2-dimethylhydrazono)-6-methyl-1,3a,4,5,6,6a- hexahydrocyclopenta[c]pyrrole-3a,6a-dicarbonitriles, and 3-(2,2-dimethylhydrazino)-5-methylcyclopent-2-ene-1,1,2-tricarbonitrile. © 2015 Pleiades Publishing, Ltd.