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.

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;FANTIN, Giancarlo;FOGAGNOLO, Marco;GIOVANNINI, Pier Paolo;MASSI, Alessandro;PACIFICO, Salvatore
2012

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.
Bertolasi, Valerio; Bortolini, Olga; A., Donvito; Fantin, Giancarlo; Fogagnolo, Marco; Giovannini, Pier Paolo; Massi, Alessandro; Pacifico, Salvatore
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11392/1690297
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