We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthesis of 5-Chloro-3-styryl-1H-pyrazoles Based on 2,2-Dichlorovinyl Ketones.
- Authors
Kobelevskaya, V. A.; Zinchenko, S. V.; Popov, A. V.
- Abstract
The condensation of 4,4-dichlorobut-3-en-2-one with aromatic aldehydes in the presence of a cata-lytic amount of sulfuric acid afforded 1,1-dichloro-5-(4-R-phenyl)penta-1,4-dien-3-ones which reacted with substituted hydrazines under mild conditions in chemo- and regioselective fashion to give 3-[(E)-2-arylethenyl]-5-chloro-1-methyl-1H-pyrazoles in up to 81% yield. The reaction of 4-bromo-1,1-dichloro-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one with N,N-dimethylhydrazine produced 3-[1-bromo-2-(4-methoxyphenyl)-ethenyl]-5-chloro-1-methyl-1H-pyrazole which was converted to 5-chloro-3-[(4-methoxyphenyl)-ethynyl]-1-methyl-1H-pyrazole in 69% yield on heating in DMSO in the presence of KF at 120°C. The structure of the synthesized compounds was confirmed by IR, NMR, and mass spectra and elemental analyses.
- Subjects
KETONES; MASS spectrometry; AROMATIC aldehydes; CHEMICAL synthesis; SULFURIC acid; HYDRAZINES; HYDRAZINE
- Publication
Russian Journal of Organic Chemistry, 2023, Vol 59, Issue 6, p1000
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428023060052