4.8 Article

Isothiourea-Mediated One-Pot Synthesis of Trifluoromethyl Substituted 2-Pyrones

Journal

ORGANIC LETTERS
Volume 16, Issue 3, Pages 964-967

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol403697h

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Funding

  1. Royal Society for a University Research Fellowship (ADS)
  2. EPSRC (DSBD) [EP/J018139/1]
  3. Engineering and Physical Sciences Research Council [EP/J018139/1] Funding Source: researchfish
  4. EPSRC [EP/J018139/1] Funding Source: UKRI

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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 alpha,beta-unsaturated trifluoro-Methyl 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.

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