Synthesis and spectroscopic properties of 9-substituted benz[g]indoles

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 photolysis 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 p...

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Bibliographic Details
Published inHeterocycles Vol. 51; no. 5; pp. 1093 - 1099
Main Authors Nagawa, Y, Honda, K, Nakanishi, H
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.05.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BASICITIES
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Summary: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 photolysis 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 in peri- position of the naphthalene ring, unique properties such as the strong intramolecular hydrogen bonding and the restricted rotation of C(sp2)-N(sp3) single bond were observed in the 9-substituted benz[g]indoles.
ISSN:0385-5414
DOI:10.3987/COM-98-8467