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Paper | Regular issue | Vol 32, No. 5, 1991, pp.1003-1012
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5720
Fused Imidazophenothiazines: Studies on the Bernthsen Thionation of 1-Methyl-6-(p-tolylamino)benzimidazole and 2-Methyl-1-phenylbenezimidazole

Pilar López-Alvarado, Carmen Avendaño,* and J. Carlos Menéndez

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain

Abstract

Thionation of 1-methyl-6-(p-tolylamino)benzimidazole (obtained from 1-methyl-6-aminobenzomidazole and p-tolyllead triacetate) afforded a 7:3 mixture of two isomeric imidazophenothiazines, by inclusion of sulphur into the C7 and C2 ’ or C5 and C2’ positions, respectively. The capability of 1-arylbenzimidazoles to cyclize to a fused imidazophenothiazine was also shown. These results are discussed in comparison to those previously obtained on 2-methyl-1-phenyl-5-phenylaminobenzimidazole, a more complex system where both diarylamine units are present.