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■ Synthesis and Spectroscopic Properties of 9-Substituted Benz[g]indoles

Yoshinobu Nagawa,* Koichi Honda, and Hiroshi Nakanishi

*National Institute of Bioscience and Human-Technology, 1-1, Higashi, Tsukuba, Ibaraki, 305-8566, Japan

Abstract

Photolysis of 1,1’-(1,8-naphthylene)di-1H-1,2,3-triazoles in methanol has given new benz[g]indoles with a triazole ring at 9-position. Similar photoreaction of 1-(8-dimethylamino-1-naphthyl)-1H-1,2,3-triazoles also gives new benz[g]indoles with a dimethylamino group at 9-position. The spectral properties of these compounds were studied in comparison with those of corresponding benz[g]indoles obtained from the similar photolysis of 1-(1-naphthyl)-1H-1,2,3-triazoles. Since the substituent at 9-position and the pyrrole moiety exist in close proximity, unique properties such as the strong intramolecular hydrogen bonding and the restricted rotation of C(sp2)-N(sp3) bond are observed in the 9-substituted benz[g]indoles.