Issue 48, 2019, Issue in Progress

Tandem grinding reactions involving aldol condensation and Michael addition in sequence for synthesis of 3,4,5-trisubstituted isoxazoles

Abstract

A one-pot, base-catalyzed, tandem grinding process involving carrying out aldol condensation and Michael addition in sequence to produce 3,4,5-trisubstituted isoxazoles from 3,5-dimethyl-4-nitroisoxazole, aromatic aldehydes and activated methylene compounds has been developed. In the presence of 10 mol% of pyrrolidine, aldol condensations of 3,5-dimethyl-4-nitroisoxazole with various aromatic aldehydes were performed with 3–10 minutes of grinding to provide 5-styryl-3-methyl-4-nitroisoxazoles in good to quantitative yields without further purification. Then, Michael additions between 5-styryl-3-methyl-4-nitroisoxazoles and activated methylene compounds (including ethyl 2-nitroacetate and alkyl 2-cyanoacetates) were carried out in the presence of 10 mol% of Et3N in the same mortar with 3–5 minutes of continuous grinding to produce 3,4,5-trisubstituted isoxazoles in good to excellent yields.

Graphical abstract: Tandem grinding reactions involving aldol condensation and Michael addition in sequence for synthesis of 3,4,5-trisubstituted isoxazoles

Supplementary files

Article information

Article type
Paper
Submitted
27 Jun 2019
Accepted
23 Aug 2019
First published
04 Sep 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 27883-27887

Tandem grinding reactions involving aldol condensation and Michael addition in sequence for synthesis of 3,4,5-trisubstituted isoxazoles

X. Hu, H. Dong, Y. Li, P. Huang, Z. Tian and P. Wang, RSC Adv., 2019, 9, 27883 DOI: 10.1039/C9RA04864B

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