title: 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.
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.
authors: Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, I-44121 Ferrara, Italy.
authors: Valerio
authors: V
authors: Bertolasi
authors: Olga
authors: O
authors: Bortolini
authors: Adelaide
authors: A
authors: Donvito
authors: Giancarlo
authors: G
authors: Fantin
authors: Marco
authors: M
authors: Fogagnolo
authors: Pier Paolo
authors: PP
authors: Giovannini
authors: Alessandro
authors: A
authors: Massi
authors: Salvatore
authors: S
authors: Pacifico