Catalytic and Multicomponent Reactions for Green Synthesis of Some Pyrazolone Compounds and Evaluation as Antimicrobial Agents

Hazim M Ali; Yasser A El-Ossaily; Saoud A Metwally; Ibrahim O Althobaiti; Hamud A Altaleb; Yousra A Naffea; Mahmoud S Tolba

doi:10.1021/acsomega.2c03070

Catalytic and Multicomponent Reactions for Green Synthesis of Some Pyrazolone Compounds and Evaluation as Antimicrobial Agents

ACS Omega. 2022 Aug 8;7(33):29142-29152. doi: 10.1021/acsomega.2c03070. eCollection 2022 Aug 23.

Authors

Hazim M Ali¹, Yasser A El-Ossaily¹, Saoud A Metwally², Ibrahim O Althobaiti¹, Hamud A Altaleb³, Yousra A Naffea⁴, Mahmoud S Tolba⁵

Affiliations

¹ Department of Chemistry,College of Science, Jouf University, Sakaka 72341, Aljouf, Saudi Arabia.
² Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt.
³ Department of Chemistry, Faculty of Science, Islamic University of Madinah, Al-Madinah, Al-Munawwarah 42351, Saudi Arabia.
⁴ Plant protection research institute, Agricultural research center, Dokki, Giza 12619, Egypt.
⁵ Chemistry Department, Faculty of Science, New Valley University, El-Kharja 72511, Egypt.

Abstract

A green synthetic approach and facile method was developed to produce pyrazole compounds (6a-d) by the reaction of ethyl acetoacetate (1), hydrazines (2a-d), and catalytic imidazole (3) in aqueous media. 4-Dicyanomethylene-2-pyrazoline-5-one derivatives (14a-d) were synthesized through the reaction of 2-pyrazoline-5-one derivatives (6a-d) with tetracyanoethylene (TCE) (7) by using catalytic imidazole (3) in an aqueous medium. Moreover, the 4-dicyanomethylene derivative (16) was obtained via treatment of 1-phenyl-3,5-pyrazolidinedione (15) with TCE (7). The spiropyrazoleoxirane derivatives (18 and 20) were prepared by treating the precursor 4-dicyanomethylene-2-pyrazoline-5-one derivative (14b) with hydrogen peroxide in various polar solvents under alkaline conditions. The spiropyrazole oxirane derivative (18) was used as a precursor for the design of functionalized pyrazolone derivatives (24 and 27a, b). The chemical structure of the novel designed derivatives was ascertained based on elemental analyses, mp, thin-layer chromatography, and spectral analyses. Furthermore, some of the synthesized derivatives were examined against different pathogenic bacterial and fungal strains. Their results demonstrated that some of them revealed notable antimicrobial activities.