4.4 Article

Regioselective microwave-assisted synthesis of substituted pyrazoles from ethynyl ketones

Journal

SYNLETT
Volume -, Issue 5, Pages 704-708

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-2007-970783

Keywords

ethynyl ketones; pyrazoles; heterocycles; microwave synthesis; concurrent heating and cooling

Funding

  1. Engineering and Physical Sciences Research Council [GR/S41463/01] Funding Source: researchfish

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Reaction of alpha,beta-ethynyl ketones and hydrazine derivatives gives 1,3- and 1, 5 -disubstituted pyrazoles in good yield. Microwave irradiation in concentrated hydrochloric acid-methanol (1.5% v/v), with concurrent cooling at sub-ambient temperatures or at 120 degrees C, for 30 or 2 minutes, respectively, facilitates rapid heterocyclization and preferentially gives the 1,3 -disubstituted regioisomer.

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