Page 42 - Book of Abstracts

th
8 Biannual Conference on Chemistry - CHEM 08

Reactivity of Aliphatic Hydrazonoyl Bromide. Synthesis of
new Derivatives of Pyrazoles, Pyrazolines, and
Pyrazolopyrimidines

Fatma M. Saleh, Monica G. Kamel,* and Hamid A. Ead
Department of Chemistry, Faculty of Science, Cairo University. Email:
monica.chemist@yahoo.com

ABSTRACT

5-Amino-3-ethyl-1-(4-nitrophenyl)-1H-pyrazole-4-carbonitrile 2 was prepared
via stirring of N-(4-nitrophenyl)-propionohydrazonoyl bromide 1 with
malononitrile in sodium ethoxide solution. The latter product 2 was converted
to formimidate 3 upon treatment with TEOF in acetic anhydride. The reaction of
compound 3 with hydrazine hydrate gave 4-imino-3-ethyl-1-(4-nitrophenyl)-1,4-
dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-amine 4. Then, refluxing of compound
4 with hydrazine hydrate afforded the corresponding hydrazino 5. Condensation
reactions of the corresponding hydrazino take place with the appropriate
aldehydes and ketones to give pyrazolo[3,4-d]pyrimidine derivatives 6a-g and
7a-g, respectively. Furthermore, reaction of the hydrazonoyl bromide 1 with
arylidenemalononitriles 8 and arylidenecyanoacetates 9 yielded the
corresponding pyrazole 10a-e and pyrazoline derivatives 11a-c, respectively.
Antimicrobial studies are performed against compounds 5, 6g, 7c, and 7e
revealed high antibacterial effect against all tested strains. Unfortunately, all
compounds have no antifungal activity against candida albicans except
compounds 6c, 7b, and 7c.
Keywords: Malononitrile, Hydrazonoyl bromide, Hydrazine hydrate,
Pyrazoles, Pyrazolopyrimidines and Condensation reactions.

BOOK OF ABSTRACTS CHEM 08 (2020) Page 41