Unexpected reactivity of diaryl α-diketones with thiazolium carbenes: discovery of a novel multicomponent reaction for the facile synthesis of 1,4-thiazin-3-ones

Org Biomol Chem. 2012 Aug 28;10(32):6579-86. doi: 10.1039/c2ob25928a. Epub 2012 Jul 6.

Abstract

Diaryl α-diketones do not undergo polarity reversal in the presence of (benzo)thiazolium carbenes but are engaged in a novel multicomponent reaction with water to efficiently give medicinally relevant 1,4-thiazin-3-one heterocycles. Three different sets of conditions have been optimized to furnish the title compounds in fair to excellent yields depending on the electronic properties of α-diketone aromatic substituents and thiazolium or benzothiazolium substrate. A plausible reaction mechanism is also proposed based on the isolation and characterization of the postulated key intermediate and isotopic labeling experiments.