Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 12, Pages 4490-4498Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9006249
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Funding
- Agencia Cordoba Ciencia
- Consejo Nacional de Investigaciones Cientfficas y Tecnicas
- Secretaria de Ciencia y Tecnologia, Universidad Nacional de Cordoba
- Fondo para la Investigacion Cientifica y Tecnologica Argentina
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The synthesis of a series of substituted 9H-carbazoles by the photostimulated SRNI substitution reaction with diarylamines as starting substrate was performed. The diarylamines were obtained by two approaches, the Pd-catalyzed reactions (Buchwald-Hartwig) or Cu-catalyzed reactions of 2-haloanilines with aryl halides, or 2-bromoiodobenzene with anilines, with moderate to very good isolated yields (45-89%). Through an intramolecular C-C bond formation of diarylamines by the SRNI mechanism, carbazoles were achieved. These reactions proceeded synthetically in very good to excellent yields (81-99%) in liquid ammonia and DMSO. The reaction of N-(2-bromophenyl)-2-phenylbenzenamine gave 1-phenyl-9H-carbazole (38%) and the isomer 9H-tribenz[b,d,f]azepine (58%). By using this methodology, 9H-carbazoles, substituted 9H-carbazoles, benzocarbazoles, and even 3,3'-bi(9H-carbazole) were obtained by a double SRNI reaction with benzidine.
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