Ghorai, Manas K. ; Shahi, Chandan Kumar ; Bhattacharyya, Aditya ; Sayyad, Masthanvali ; Mal, Abhijit ; Wani, Imtiyaz Ahmad ; Chauhan, Navya (2015) Syntheses of Tetrahydrobenzodiazepines via SN2-Type Ring-Opening of Activated Aziridines with 2-Bromobenzylamine Followed by Copper-Powder-Mediated C−N Bond Formation Asian Journal of Organic Chemistry, 4 (10). pp. 1103-1111. ISSN 2193-5807
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Official URL: http://doi.org/10.1002/ajoc.201500224
Related URL: http://dx.doi.org/10.1002/ajoc.201500224
Abstract
A synthetic route to 2,3,4,5‐tetrahydrobenzodiazepines has been devised through an SN2‐type ring‐opening of N‐activated aziridines with 2‐bromobenzylamine followed by an intramolecular cyclization through Cu‐powder‐mediated C−N bond formation. This operationally simple and extremely stereospecific ring‐opening‐cyclization approach is very efficient for the synthesis of a diverse array of the desired benzodiazepine derivatives in excellent yields of up to 94 % and enantiomeric excess of up to >99 %.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley & Sons, Inc. |
| Keywords: | 2-bromobenzylamine; Copper; Cyclization; Nitrogen Heterocycles; Tetrahydrobenzodiazepines. |
| ID Code: | 117103 |
| Deposited On: | 15 Apr 2021 07:53 |
| Last Modified: | 15 Apr 2021 07:53 |
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