23933-00-8Relevant academic research and scientific papers
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
Bertolasi, Valerio,Bortolini, Olga,Donvito, Adelaide,Fantin, Giancarlo,Fogagnolo, Marco,Giovannini, Pier Paolo,Massi, Alessandro,Pacifico, Salvatore
supporting information; experimental part, p. 6579 - 6586 (2012/09/08)
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.
