title: 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.
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews , North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom.
authors.forename: Pei-Pei
authors.initials: PP
authors.lastname: Yeh
authors.forename: David S B
authors.initials: DS
authors.lastname: Daniels
authors.forename: David B
authors.initials: DB
authors.lastname: Cordes
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D002384:Catalysis; D052246:Cyclooxygenase 2 Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry*
chemical_list: D052246:Cyclooxygenase 2 Inhibitors; D006845:Hydrocarbons, Fluorinated; D011753:Pyrones; D013890:Thiourea