Microwave‐assisted synthesis and biological evaluation of pyrazole‐4‐carbonitriles as antimicrobial agents,Journal of Heterocyclic Chemistry

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Microwave‐assisted synthesis and biological evaluation of pyrazole‐4‐carbonitriles as antimicrobial agents
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-05-06 , DOI: 10.1002/jhet.4003
Sumit Sood ₁ , Poonam Kumari ₁ , Ajar Nath Yadav ₂ , Anil Kumar ₁ , Karan Singh ₁

Affiliation

An efficient microwave‐assisted method of synthesis of pyrazole‐4‐carbonitriles has been developed. Condensation of pyrazole‐4‐carbaldehydes with hydroxylamine hydrochloride followed by reaction of the resulting oximes with the Vilsmeier‐Haack reagent pre‐formed from phthaloyl dichloride and dimethylformamide under microwave irradiation afforded the corresponding pyrazole‐4‐carbonitriles in 73% to 91% yield. The operational simplicity, avoidance of toxic reagents such as POCl₃, shorter reaction time, higher yield compared to the classical version, easy work up, and the use of the by‐product in the regeneration of phthaloyl dichloride are the advantages of this methodology. All the target compounds were tested for antimicrobial activity against Gram‐positive bacteria Bacillus cereus and Staphylococcus aureus ; Gram‐negative bacteria Escherichia coli and Yersinia enterocolitica , and the fungal species Candida albicans .

中文翻译：

微波辅助合成吡唑-4-腈作为抗微生物剂

已经开发了一种高效的微波辅助合成吡唑-4-腈的方法。在微波辐射下将吡唑-4-甲醛与盐酸羟胺缩合，然后使肟与由邻苯二甲酰氯和二甲基甲酰胺预先形成的Vilsmeier-Haack试剂反应，得到相应的吡唑-4-腈，收率为73％至91％。该方法的优点是操作简便，避免使用POCl ₃等有毒试剂，比传统方法更短的反应时间，更高的收率，易于加工以及在邻苯二甲酰二氯再生中使用副产物。测试所有目标化合物对革兰氏阳性细菌蜡样芽孢杆菌的抗菌活性和金黄色葡萄球菌; 革兰氏阴性细菌大肠杆菌和小肠结肠炎耶尔森氏菌，以及白色念珠菌属真菌。

更新日期：2020-07-15

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