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

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 S 2-type regioselective ring opening of enantiopure aziridines with 2-(2-bromophenyl...

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Veröffentlicht in:Organic letters 2017-07, Vol.19 (13), p.3438-3441
Hauptverfasser: Pradhan, Sajan, Shahi, Chandan Kumar, Bhattacharyya, Aditya, Chauhan, Navya, Ghorai, Manas K
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container_end_page 3441
container_issue 13
container_start_page 3438
container_title Organic letters
container_volume 19
creator Pradhan, Sajan
Shahi, Chandan Kumar
Bhattacharyya, Aditya
Chauhan, Navya
Ghorai, Manas K
description 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 S 2-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%).
doi_str_mv 10.1021/acs.orglett.7b01397
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title Syntheses of Tetrahydrobenzoazepinoindoles and Dihydrobenzodiazepinoindoles via Ring-Opening Cyclization of Activated Aziridines with 2-(2-Bromophenyl)-1H-indoles
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