2,2-dichlorovinulketones-based 5-chloro-3-styryl-1H-pyrazoles synthesis

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Resumo

Condensation of 4,4-dichlorobut-3-en-2-one with aromatic aldehydes in the presence of catalytic amounts of sulfuric acid leads to the formation of 1,1-dichloro-5-(4-R-phenyl)penta-1,4-diene-3-ones. The reaction of 1,4-dien-3-ones with hydrazines proceeds chemo- and regioselectively under mild conditions with the formation of ( E )-1-methyl-3-styryl-5-chloro-1 H -pyrazoles with a yield reaching 81%. 4-Bromo-1,1-dichloro-5-(4-methoxyphenyl)penta-1,4-dien-3-one reacts with dimethylhydrazine to give 3-[1-bromo-2-(4-methoxyphenyl)vinyl]-5chloro-1-methyl-1 H -pyrazole, which in the presence of KF in DMSO at 120°C forms 1-methyl-3-[(4-methoxyphenyl)ethynyl]-5-chloro-1 H -pyrazole with 69% yield. The structure of the synthesized compounds has been confirmed using IR, NMR spectroscopies, mass spectrometry, and elemental analysis.

Sobre autores

V. Kobelevskaya

A.E. Favorsky Irkutsk Institute of Chemistry, SB RAS

Email: valkob@irioch.irk.ru

S. Zinchenko

A.E. Favorsky Irkutsk Institute of Chemistry, SB RAS

A. Popov

A.E. Favorsky Irkutsk Institute of Chemistry, SB RAS

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