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EnglishDiaryl 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.
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| Data di pubblicazione: | 2012 | |
| Titolo: | 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 | |
| Autori: | V. Bertolasi; O. Bortolini; A. Donvito; G. Fantin; M. Fogagnolo; P. P. Giovannini; A. Massi; S. Pacifico | |
| Rivista: | ORGANIC & BIOMOLECULAR CHEMISTRY | |
| 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. | |
| Digital Object Identifier (DOI): | 10.1039/c2ob25928a | |
| Handle: | http://hdl.handle.net/11392/1690297 | |
| Appare nelle tipologie: | 03.1 Articolo su rivista |
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