Issue 8, 2015

Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines

Abstract

Enantiomerically-enriched trichloromethyl-containing alcohols, obtained by asymmetric reduction, can be transformed regioselectively into 1-substituted piperazinones by modified Jocic reactions with little or no loss of stereochemical integrity. This methodology can be easily used to synthesise important pharmaceutical compounds such as the fluorobenzyl intermediate of a known PGGTase-I inhibitor.

Graphical abstract: Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines

Supplementary files

Article information

Article type
Paper
Submitted
30 Oct 2014
Accepted
16 Dec 2014
First published
16 Dec 2014

Org. Biomol. Chem., 2015,13, 2360-2365

Author version available

Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines

M. S. Perryman, M. W. M. Earl, S. Greatorex, G. J. Clarkson and D. J. Fox, Org. Biomol. Chem., 2015, 13, 2360 DOI: 10.1039/C4OB02311K

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