Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives
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- 作者：Korany A. Ali ; Eman Ali Ragab ; Heba S. Abdelghafar…
- 关键词：Pyrazole ; 4 ; carbonitrile ; Binucleophiles ; Chalcone ; Multicomponent condensation reactions (MCRs) ; Pyrimidine
- 刊名：Research on Chemical Intermediates
- 出版年：2016
- 出版时间：April 2016
- 年：2016
- 卷：42
- 期：4
- 页码：3553-3566
- 全文大小：924 KB
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20.K.M. Dawood, E.A. Ragab, A.M. Farag, J. Chem. Res. 11, 1151–1160 (2003) - 作者单位：Korany A. Ali (1)
Eman Ali Ragab (2)
Heba S. Abdelghafar (1)
Ahmad M. Farag (2)
1. Applied Organic Chemistry Department, Center of Excellence for Advanced Science, National Research Centre, Dokki, Giza, 12622, Egypt
2. Departments of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Catalysis
Physical Chemistry
Inorganic Chemistry - 出版者：Springer Netherlands
- ISSN：1568-5675
文摘
Aldol condensation of 3-acetyl-1-(4-fluorophenyl)-5-phenyl-1H-pyrazole-4-carbonitrile with benzaldehyde afforded 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile, which in turn reacted with a series of 1,2- and 1,3-binucleophiles to afford new substituted pyrazoles, pyrimidines, and condensed azolopyrimidine derivatives attached to pyrazole scaffold at position 3. Moreover, multicomponent condensation reactions (MCRs) were used as an alternative method, and 1H–13C heteronuclear single quantum coherence (HSQC) in addition to heteronuclear multiple-bond correlation (HMBC) spectra were used for full confirmation of a selected example of these compounds. The reactivity of 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile towards active methylene derivatives, including malononitrile and ethyl cyanoacetate, was explored and afforded 2-amino-6-(4-cyano-1-(4-fluorophenyl)-5-phenyl-1H-pyrazol-3-yl)-4-phenylpyridine-3-carbonitrile and ethyl 6-(4-cyano-1-(4-fluorophenyl)-5-phenyl-1H-pyrazol-3-yl)-1,2-dihydro-2-oxo-4-phenylpyridine-3-carboxylate, respectively.