Issue 3, 2016

N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes

Abstract

An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.

Graphical abstract: N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes

Supplementary files

Article information

Article type
Communication
Submitted
30 Sep 2015
Accepted
02 Dec 2015
First published
10 Dec 2015

Org. Biomol. Chem., 2016,14, 858-861

N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes

M. H. Shinde and U. A. Kshirsagar, Org. Biomol. Chem., 2016, 14, 858 DOI: 10.1039/C5OB02034D

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