Nair, Deepa ; Pavashe, Prashant ; Namboothiri, Irishi N.N. (2018) 1,3-Dipolar cycloaddition of chalcones and arylidene-1,3-dicarbonyls with diazosulfone for the regioselective synthesis of functionalized pyrazoles and pyrazolines Tetrahedron, 74 (22). pp. 2716-2724. ISSN 0040-4020
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Official URL: http://doi.org/10.1016/j.tet.2018.04.030
Related URL: http://dx.doi.org/10.1016/j.tet.2018.04.030
Abstract
A convenient method for the synthesis of 3-acylpyrazoles and pyrazole-3-carboxylates using diazosulfone as a reactive 1,3-dipole and a diazomethane equivalent is reported here. Chalcones, arylidenemalonates and other arylidene-1,3-dicarbonyls performed well as the dipolarophiles in the reaction with the diazosulfone which took place under simple base mediated conditions (Cs2CO3 or NaOEt in EtOH). In few cases, the initial cycloadducts, the intermediate pyrazoline derivatives, could also be isolated and characterized. The pyrazoline derivatives undergo an alkoxide mediated 1,4-elimination, viz. decarboxylation-detosylation to afford the pyrazole derivatives.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Chalcones; Arylidene-1,3-Dicarbonyls; Diazosulfone3-substituted pyrazoles; Decarboxylation-Detosylation. |
| ID Code: | 121319 |
| Deposited On: | 14 Jul 2021 09:31 |
| Last Modified: | 14 Jul 2021 09:31 |
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