Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones
Abstract
A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.
Citation
Yeh , P-P , Daniels , D S B , Cordes , D B , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones ' Organic Letters , vol 16 , no. 3 , pp. 964-967 . DOI: 10.1021/ol403697h
Publication
Organic Letters
Status
Peer reviewed
ISSN
1523-7060Type
Journal article
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © 2014 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol403697h
Description
The authors thank the Royal Society for a University Research Fellowship (ADS) and the EPSRC (EP/J018139/1, DSBD) for funding.Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.