152675

Synthesis and biological activity of a new class of enaminonitrile pyrazole

Article

Last updated: 01 Jan 2025

Subjects

-

Tags

Organic chemistry

Abstract

The present work illustrates the treatment of 5-amino-1,3-diphenyl-1H-pyrazole-4-carbonitrile (1) with maleic, phthalic anhydrides, acetyl chloride, and benzene sulfonyl chloride to afford the pyrazole derivatives 2-5. The treatment of pyrazole derivative 1 with some active methylene reagents namely: malononitrile, cyanoacetamide, ethyl acetoacetate afforded the pyrazolopyridine 6-9. Reaction of compound 1 with acetic anhydride gave the pyrazolopyrimidinone 10, which was allowed to react with P2S5 and POCl3 to give the thione 11 and the chloro 12 derivatives. The reaction of compounds 11 and 12 with thiosemicarbazide under different conditions gave 13 and 14. Compound 12 when reacted with hydrazine hydrate and p-toluidine gave compounds 15 and 16. The reaction of compound 10 with ethyl chloroacetate gave compound 17 which was allowed to react with thiosemicarbazide to give 22 and also to consecutive reactions with hydrazine hydrate, carbon disulfide, piperidine, hydrazine hydrate to give compounds 18-21. Finally, compound 1 was reacted with chloroacetic acid, hydrated hydrazine, urea, thiourea, benzaldehyde and triethylamine to give compounds 23-29. The newly prepared compounds were characterized by using IR, 13C-NMR, 1H-NMR, and mass spectral data. Some new pyrazole derivatives showed highly antibacterial activities.

DOI

10.21608/ejchem.2021.62916.3350

Keywords

pyrazole, pyrazolopyrimidine, Pyrazolopyridine, Antibacterial

Authors

First Name

sabah

Last Name

Mohamed

MiddleName

-

Affiliation

research at the Regional Center of Mycology and Biotechnology, Al-Azhar University, Cairo, Egypt.

Email

sabah.sobhey@yahoo.com

City

-

Orcid

-

First Name

nadia

Last Name

dawoud

MiddleName

-

Affiliation

Professor of Organic Chemistry at Faculty of Science, Al-Azhar University (for girls), Nasr City, Cairo, Egypt.

Email

dawoudnad@yahoo.com

City

Cairo

Orcid

-

First Name

Sara N.

Last Name

Shabaan

MiddleName

-

Affiliation

Associate professor at Faculty of Science, Al-Azhar University (for girls), Nasr City, Cairo, Egypt.

Email

saranabil299@gmail.com

City

-

Orcid

-

First Name

nahed

Last Name

fathall

MiddleName

-

Affiliation

Professor of Organic Chemistry at Faculty of Science, Al-Azhar University (for girls), Nasr City, Cairo, Egypt.

Email

profnahed@yahoo.com

City

Cairo

Orcid

-

First Name

galal

Last Name

hosni

MiddleName

-

Affiliation

Professor of Organic Chemistry at Faculty of Science, Ain Shams University, Cairo, Egypt.

Email

galal.hosny.sayed@gamil.com

City

Cairo

Orcid

-

First Name

kurls

Last Name

anwer

MiddleName

ekram

Affiliation

chemistry, faculty of science, ain shams, cairo, egypt

Email

kurls_koko@yahoo.com

City

-

Orcid

-

Volume

64

Article Issue

6

Related Issue

24623

Issue Date

2021-06-01

Receive Date

2021-02-13

Publish Date

2021-06-01

Page Start

3,187

Page End

3,203

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_152675.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=152675

Order

49

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

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

MainTitle

Synthesis and biological activity of a new class of enaminonitrile pyrazole

Details

Type

Article

Created At

22 Jan 2023