An efficient regioselective copper catalyzed multi-component synthesis of 1,3-disubstituted pyrazoles

An efficient synthesis of unsymmetrically substituted 1,3-pyrazole derivatives has been developed via three-component coupling reaction involving 3-(dimethylamino)-1-phenylprop-2-en-1-one, hydrazine, and aryl halides in one pot process exhibiting high regioselectivity. The pyrazole synthesis proceed...

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Bibliographic Details
Published in:Tetrahedron letters 2014-04, Vol.55 (18), p.2986-2990
Main Authors: Raghunadh, Akula, Meruva, Suresh Babu, Mekala, Ramamohan, Raghavendra Rao, K., Krishna, Thalishetti, Gangadhara Chary, R., Vaikunta Rao, L., Syam Kumar, U.K.
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical reactions
Cross coupling
Cu catalyst and Ullmann cross-coupling reaction
Derivatives
Hydrazines
Michael addition
Multicomponent reaction
Pyrazole
Pyrazoles
Synthesis (chemistry)
Tetrahedrons
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Summary:An efficient synthesis of unsymmetrically substituted 1,3-pyrazole derivatives has been developed via three-component coupling reaction involving 3-(dimethylamino)-1-phenylprop-2-en-1-one, hydrazine, and aryl halides in one pot process exhibiting high regioselectivity. The pyrazole synthesis proceeds via a sequential series of reactions such as Michael addition, heterocyclization, dehydration, and Ullmann cross-coupling.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.03.125