5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile as Precursor for synthesis of some novel pyrazolo[1,5-a]pyrimidine derivatives
El-Qaliei, M., Mousa, S., M. D. Nasr, H., A. Ìshak, E. (2022). 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile as Precursor for synthesis of some novel pyrazolo[1,5-a]pyrimidine derivatives. EKB Journal Management System, 65(11), 331-340. doi: 10.21608/ejchem.2022.124950.5560
Mohamed I. H. El-Qaliei; Sayed A. S. Mousa; Hamdi M. D. Nasr; Esam A. Ìshak. "5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile as Precursor for synthesis of some novel pyrazolo[1,5-a]pyrimidine derivatives". EKB Journal Management System, 65, 11, 2022, 331-340. doi: 10.21608/ejchem.2022.124950.5560
El-Qaliei, M., Mousa, S., M. D. Nasr, H., A. Ìshak, E. (2022). '5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile as Precursor for synthesis of some novel pyrazolo[1,5-a]pyrimidine derivatives', EKB Journal Management System, 65(11), pp. 331-340. doi: 10.21608/ejchem.2022.124950.5560
El-Qaliei, M., Mousa, S., M. D. Nasr, H., A. Ìshak, E. 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile as Precursor for synthesis of some novel pyrazolo[1,5-a]pyrimidine derivatives. EKB Journal Management System, 2022; 65(11): 331-340. doi: 10.21608/ejchem.2022.124950.5560

5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile as Precursor for synthesis of some novel pyrazolo[1,5-a]pyrimidine derivatives

Egyptian Journal of Chemistry
Article 30, Volume 65, Issue 11, November 2022, Page 331-340  XML PDF (589.27 K)
Document Type: Original Article
DOI: 10.21608/ejchem.2022.124950.5560
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Authors
Mohamed I. H. El-Qaliei email orcid 1; Sayed A. S. Mousaorcid 1; Hamdi M. D. Nasr2; Esam A. Ìshak3
1Department of Chemistry, Faculty of Science, Al-Azhar University at Assiut, Assiut
2Department of Chemistry, Faculty of Science, Al-Azhar University at assiut, Assiut, Egypt
3Department of Chemistry, Faculty of Science, Al-Azhar University at assiut, 71524, Assiut, Egypt
Abstract
New pyrazolo[1,5-a]pyrimidine-3-carbonitrile 5 was obtained by reaction of 5-amino-3-cyanomethyl-1H-pyrazole-4-carbonitrile 3 with enamine of acetylacetone 2. Coupling of compound 5 with aryldiazonium chloride 6a-c afforded pyrimido[1',2':1,5]pyrazolo[3,4-d]pyridazine derivatives 8. Also, condensation of compound 5 with aromatic aldehydes 9a-c gives the corresponding arylidene derivatives 10. stirring of compound 5 with phenyl isothiocyanate in presence of potassium hydroxide, followed by addition of phencyl bromide derivatives 13a-c or chloroacetonitrile 18 afforded (thiophen-3-yl)-7-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 16a-c and 20 which cyclized by refluxing in ethanolic sodium ethoxide solution to afforded thieno[3'',4'':5',6']pyrido [4',3':3,4]pyrazolo[1,5-a]pyrimidine derivatives 17a-c and 21.
Keywords
Pyrazolo; Pyrimidine; Arylidene; Phenyl bromide
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