Beta
317071

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

Article

Last updated: 01 Jan 2025

Subjects

-

Tags

-

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.

DOI

10.21608/ejchem.2023.231631.8493

Keywords

pyrazolo[1, 5-a]pyrimidine, 5-Aminopyrazole, Enaminones, THIOPHENE, Carbonitrile

Authors

First Name

mustafa

Last Name

Alqadhi

MiddleName

abdosalam

Affiliation

Department of Medicinal Chemistry, Faculty of Pharmacy, Sana'a University, P.O. Box, 18084, Sana'a, Yemen

Email

m777329509@gmail.com

City

-

Orcid

-

First Name

Heba

Last Name

Allam

MiddleName

-

Affiliation

Faculty of Pharmacy, Cairo University

Email

heba.abdelkhalek@pharma.cu.edu.eg

City

-

Orcid

0000-0001-6176-7035

First Name

Samar

Last Name

Fahim

MiddleName

Hashem

Affiliation

faculty of pharmacy Cairo university

Email

samarhfmy@hotmail.com

City

-

Orcid

-

First Name

Tawfeek

Last Name

Yahya

MiddleName

A.A.

Affiliation

Department of Medicinal Chemistry, Faculty of Pharmacy, Sana'a University, P.O. Box, 18084, Sana'a, Yemen

Email

alobaidytawfeek@gmail.com

City

-

Orcid

-

First Name

Fatmaa

Last Name

Ragab

MiddleName

A.

Affiliation

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Cairo University

Email

fatmarag@cu.edu.eg

City

-

Orcid

-

Volume

67

Article Issue

3

Related Issue

45192

Issue Date

2024-03-01

Receive Date

2023-08-28

Publish Date

2024-03-01

Page Start

475

Page End

482

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_317071.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=317071

Order

317,071

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

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

Details

Type

Article

Created At

30 Dec 2024