SYNTHESIS OF 4-ETHOXYCARBONYL(CYANO)-β-CARBOLINES <i>via</i> THERMOLYSIS OF 4-ARYL-3(5)-AZIDOPYRIDINE DERIVATIVES AND THE STUDY OF THEIR OPTICAL AND HYPOGLYCEMIC PROPERTIES
DOI:
https://doi.org/10.1007/5966Keywords:
azidopyridine, Hantzsch nitropyridines, pyrido[3, 4-c]cinnoline, 9H-pyrido[3, 4-b]indole, azo coupling, Cadogan reaction, cyclization.Abstract
4-Ethoxycarbonyl(cyano)-1,3-dimethyl-β-carbolines were synthesized via thermolysis of 4-aryl-3(5)-azidopyridines and their optical and hypoglycemic properties were studied. For the first time, the accessible Hantzsch nitropyridines were used as the starting materials. Diazotization of 3-aminopyridines having a trimethoxyaryl substituent at the C-4 position of the pyridine ring by intramolecular azo coupling afforded 7,8,9-trimethoxy-2,4-dimethylpyrido[3,4-c]cinnolines. When evaluating the hypoglycemic properties of the four obtained β-carbolines, it was found that ethyl 7-fluoro-1,3-dimethyl-9H-pyrido[3,4-b]indole-4-carboxylate, the structure of whichcontains the fluorine atom, has the highest glucose-lowering action.
