Synthesis of Pyrazolone Derivatives by Grinding, Microwave, and Conventional Techniques and Their Antimicrobial Activity
Naguib, HM; Dauoud, NT; Shaban, SN; Abdelghaffar, NF; Sayed, GH; Kurls Ekram Anwer;
Abstract
Abstract: 4-(Arylmethylidene)-5-methyl-2,4-dihydro-3H-pyrazol-3-ones were prepared via one-pot reaction of ethyl acetoacetate, hydrazine hydrate, and aromatic aldehydes using mechanical grinding, microwave irradiation, and conventional techniques. These compounds were reacted with ethyl cyanoacetate, urea, hydrazine hydrate, phenylhydrazine, thiosemicarbazide, and POCl3/PCl5 to afford pyranopyrazole, pyrazolopyrimidine, 4-(α-hydrazinylbenzyl)pyrazolone, pyrazolopyrazole, and 4-(arylmethylidene)-3-chloro-5-methyl-4H-pyrazole derivatives, respectively. Reactions of the latter with aromatic amines and hydrazine hydrate gave the corresponding 3-anilino- and 3-hydrazinylpyrazoles, respectively. Reactions of 4-(arylmethylidene)-3-hydrazinyl-5-methyl-4H-pyrazoles with acetophenone, ethyl acetoacetate, acetylacetone, diethyl malonate, ethyl cyanoacetate, and chloroacetyl chloride were also studied. The yield economy, atom economy, optimum efficiency, and reaction mass efficiency were used to compare the three synthetic techniques. The new compounds were evaluated for their in vitro antibacterial and antifungal activities, and some of them showed very strong antimicrobial activity.
Other data
Title | Synthesis of Pyrazolone Derivatives by Grinding, Microwave, and Conventional Techniques and Their Antimicrobial Activity | Authors | Naguib, HM; Dauoud, NT; Shaban, SN; Abdelghaffar, NF; Sayed, GH; Kurls Ekram Anwer | Keywords | pyrazolone; ; ; ; ; ; ; BIOLOGICAL-ACTIVITY; ANTIBACTERIAL; NANOHYBRIDS;microwave;grinding;conventional heating;antibacterial activity;antifungal activity;CORROSION INHIBITION | Issue Date | 2022 | Publisher | MAIK NAUKA/INTERPERIODICA/SPRINGER | Journal | RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | Volume | 58 | Start page | 891 | End page | 904 | ISSN | 1070-4280 | DOI | 10.1134/S1070428022060203 | Scopus ID | 2-s2.0-85135617728 | Web of science ID | WOS:000837686700020 |
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