Synthesis of Some Pyrazolo[1,5-A]Pyrimidine Derivatives Bearing Carbonitrile, Amidoxime, Carboxamide And Oxadiazole Substituents Using Commercially Available Reagents
Alqadhi, M., Allam, H., Fahim, S., Yahya, T., Ragab, F. (2024). Synthesis of Some Pyrazolo[1,5-A]Pyrimidine Derivatives Bearing Carbonitrile, Amidoxime, Carboxamide And Oxadiazole Substituents Using Commercially Available Reagents. EKB Journal Management System, 67(3), 475-482. doi: 10.21608/ejchem.2023.231631.8493
mustafa abdosalam Alqadhi; Heba Allam; Samar Hashem Fahim; Tawfeek A.A. Yahya; Fatmaa A. Ragab. "Synthesis of Some Pyrazolo[1,5-A]Pyrimidine Derivatives Bearing Carbonitrile, Amidoxime, Carboxamide And Oxadiazole Substituents Using Commercially Available Reagents". EKB Journal Management System, 67, 3, 2024, 475-482. doi: 10.21608/ejchem.2023.231631.8493
Alqadhi, M., Allam, H., Fahim, S., Yahya, T., Ragab, F. (2024). 'Synthesis of Some Pyrazolo[1,5-A]Pyrimidine Derivatives Bearing Carbonitrile, Amidoxime, Carboxamide And Oxadiazole Substituents Using Commercially Available Reagents', EKB Journal Management System, 67(3), pp. 475-482. doi: 10.21608/ejchem.2023.231631.8493
Alqadhi, M., Allam, H., Fahim, S., Yahya, T., Ragab, F. Synthesis of Some Pyrazolo[1,5-A]Pyrimidine Derivatives Bearing Carbonitrile, Amidoxime, Carboxamide And Oxadiazole Substituents Using Commercially Available Reagents. EKB Journal Management System, 2024; 67(3): 475-482. doi: 10.21608/ejchem.2023.231631.8493

Synthesis of Some Pyrazolo[1,5-A]Pyrimidine Derivatives Bearing Carbonitrile, Amidoxime, Carboxamide And Oxadiazole Substituents Using Commercially Available Reagents

Egyptian Journal of Chemistry
Volume 67, Issue 3, March 2024, Page 475-482  XML PDF (384.53 K)
Document Type: Original Article
DOI: 10.21608/ejchem.2023.231631.8493
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Authors
mustafa abdosalam Alqadhi1; Heba Allamorcid 2; Samar Hashem Fahim email 3; Tawfeek A.A. Yahya1; Fatmaa A. Ragab4
1Department of Medicinal Chemistry, Faculty of Pharmacy, Sana'a University, P.O. Box, 18084, Sana'a, Yemen
2Faculty of Pharmacy, Cairo University
3faculty of pharmacy Cairo university
4Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University
Abstract
Herein we report the synthesis of some new pyrazolo[1,5-a]pyrimidine derivatives. 7-(Aryl)-2-methyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile derivatives 9a-e which were synthesized by the condensation reaction of the amino pyrazole 3 with acetylacetone 4 or with the arylpropenones (enaminones) 8a-e in acetic acid. The reaction of the carbonitrile derivative 9e with hydroxylamine in presence of sodium acetate afforded the corresponding amidoxime derivative 10. Additionally, cyclization of the amidoxime 10 to the corresponding methyl- and phenyl- 1,2,4-oxadiazoles, 11a and 11b, was accomplished by heating it with acetic-anhydride or benzoyl chloride in pyridine. On the other hand, the cyano group present in 2-methyl-7-(thiophen-2-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile 9e was partially hydrolyzed with sulphuric acid to afford the carboxamide 12. Based on their spectral information, the structures of the newly synthesized chemical derivatives were determined.
Keywords
pyrazolo[1; 5-a]pyrimidine; 5-aminopyrazole; enaminones; thiophene; carbonitrile
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