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1,3-Dipolar cycloaddition of chalcones and arylidene-1,3-dicarbonyls with diazosulfone for the regioselective synthesis of functionalized pyrazoles and pyrazolines

Authors
  • NAIR, D
  • PAVASHE, P
  • NAMBOOTHIRI, INN
Publication Date
Dec 03, 2018
Source
DSpace at IIT Bombay
Keywords
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Abstract

A convenient method for the synthesis of 3-acylpyrazoIes 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. (C) 2018 Elsevier Ltd. All rights reserved.

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