Shahi, Chandan Kumar ; Bhattacharyya, Aditya ; Nanaji, Yerramsetti ; Ghorai, Manas K. (2017) A Stereoselective Route to Tetrahydrobenzoxazepines and Tetrahydrobenzodiazepines via Ring-Opening and Aza-Michael Addition of Activated Aziridines with 2-Hydroxyphenyl and 2-Aminophenyl Acrylates The Journal of Organic Chemistry, 82 (1). pp. 37-47. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.6b01919
Related URL: http://dx.doi.org/10.1021/acs.joc.6b01919
Abstract
A simple and efficient synthetic route to 2,3,4,5-tetrahydrobenzoxazepines and -benzodiazepines bearing easily functionalizable appendages has been developed by ring-opening of activated aziridines with 2-hydroxyphenyl acrylates and 2-aminophenyl acrylate, respectively, and subsequent intramolecular C–N bond formation through palladium-catalyzed aza-Michael reaction. The straightforward synthetic approach delivers the desired molecular scaffolds in high yields (up to 82%) with excellent stereoselectivity (ee up to 94%).
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 117097 |
Deposited On: | 15 Apr 2021 07:50 |
Last Modified: | 15 Apr 2021 07:50 |
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