Organic Letters
Organic Letters
5 years ago

Syntheses of Tetrahydrobenzoazepinoindoles and Dihydrobenzodiazepinoindoles via Ring-Opening Cyclization of Activated Aziridines with 2-(2-Bromophenyl)-1H-indoles

Syntheses of Tetrahydrobenzoazepinoindoles and Dihydrobenzodiazepinoindoles via Ring-Opening Cyclization of Activated Aziridines with 2-(2-Bromophenyl)-1H-indoles
Sajan Pradhan, Chandan Kumar Shahi, Manas K. Ghorai, Aditya Bhattacharyya, Navya Chauhan
Two efficient, modular, step- and pot-economic strategies to access various 5,6,7,12-tetrahydrobenzo[2,3]azepino[4,5-b]indoles and 6,7-dihydro-5H-benzo[5,6][1,4]diazepino[1,7-a]indoles are disclosed that advance via SN2-type regioselective ring opening of enantiopure aziridines with 2-(2-bromophenyl)-1H-indoles at their C3 and indolyl N centers, respectively, followed by Cu-mediated C–N cyclization which furnishes the products in excellent yields with outstanding enantiomeric excesses (up to >99%).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01397

DOI: 10.1021/acs.orglett.7b01397

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