Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

被引:0
作者
Law, Jarvis [1 ]
Manjunath, Aashrita [1 ]
Schioldager, Ryan [1 ]
Eagon, Scott [1 ]
机构
[1] Calif Polytech State Univ San Luis Obispo, Dept Chem & Biochem, San Luis Obispo, CA 93407 USA
来源
JOVE-JOURNAL OF VISUALIZED EXPERIMENTS | 2019年 / 148期
关键词
Chemistry; Issue; 148; pyrazole-5-amines; microwave synthesis; heterocycles; green chemistry; cyclization; phenylhydrazine; alpha-cyanoketone; 3-aminocrotononitrile; DERIVATIVES; DISCOVERY;
D O I
10.3791/59896
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
A synthetic process for the preparation of a variety of 1-aryl-1H-pyrazole-5-amines was developed. The microwave-mediated nature of this method makes it efficient in both time and resources and utilizes water as the solvent. 3-Aminocrotononitrile or an appropriate a-cyanoketone is combined with an aryl hydrazine and dissolved in 1 M HCl. The mixture is then heated in a microwave reactor at 150 degrees C, typically for 10-15 min. The product can be readily obtained by basifying the solution with 10% NaOH and isolating the desired compound with a simple vacuum filtration. The use of water as a solvent in this reaction lends to its ease and utility in production, and this method is easily reproducible with a variety of functional groups. Typical isolated yields range from 70-90%, and reactions can be performed on the milligram to gram scale with little to no change in observed yields. Some of the applications of these molecules and their derivatives include pesticides, anti-malarials, and chemotherapeutics, among many others.
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