Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

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 . https://doi.org/10.1021/ol403697h

Publication

Organic Letters

Status

Peer reviewed

DOI

https://doi.org/10.1021/ol403697h

ISSN

1523-7060

Type

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

University of St Andrews Research

URI

http://hdl.handle.net/10023/6013