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Three‐Component Domino HWE Olefination/1,3‐Dipolar Cycloaddition/Oxidation Strategy for the Rapid Synthesis of Trisubstituted Pyrazoles
Author(s) -
Ahamad Shakir,
Kant Ruchir,
Mohanan Kishor
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601113
Subject(s) - domino , reagent , cycloaddition , chemistry , cascade reaction , combinatorial chemistry , organic chemistry , tandem , component (thermodynamics) , 1,3 dipolar cycloaddition , catalysis , materials science , physics , thermodynamics , composite material
A mild, general and operationally simple method for the synthesis of 3,4,5‐trisubstituted pyrazoles via a domino Horner‐Wadsworth‐Emmons olefination/1,3‐dipolar cycloaddition/oxidation cascade has been developed. This three‐component strategy employs commercially available aldehydes, β‐ketophosphonates and the Bestmann‐Ohira reagent, and delivers a variety of phosphonylpyrazoles in good to excellent yields. In addition, the advantage of using the domino procedure over stepwise process has been demonstrated.