Work

Synthesis of Isoxazol-5-One Derivatives Catalyzed by Amine-Functionalized Cellulose

Year: 2024

Type: article

Abstract: In this contribution, propylamine-functionalized cellulose (Cell-Pr-NH2) was employed as the catalyst in the three-component reaction between hydroxylamine hydrochloride and various types of aryl/heteroaryl aldehydes, ethyl acetoacetate/ethyl 4-chloroacetoacetate, or ethyl 3-oxohexanoate. The result of these experiments was the formation of 3,4-disubstituted isoxazol-5(4H)-one heterocycles. The desired five-membered heterocyclic compounds were obtained in good to high yields at room temperature. The investigation of different solvents led us to the conclusion that water is the best solvent to perform the current one-pot, three-component reactions. Attempts to find the optimal catalyst loading clearly showed that 14 mg of cell-Pr-NH2 seems to be sufficient to carry out the reactions. This method has highlighted some principles of green chemistry including less waste generation, atom economy, use of water as an environmentally friendly solvent, and energy saving. Purification without chromatographic methods, mild reaction conditions, simple work-up, low-cost reaction medium, saving time, and obtainable precursors are other notable features of this one-pot fashion.

Source: Organics

DOI: 10.3390/org5040020

Authors: Sanaz Gharehassanlou, Hamzeh Kiyani

Institutions: Damghan University, Shahrekord University

Language: English

Topic: Multicomponent Synthesis of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Responsible consumption and production

Open Access status: gold

Estimated APC paid: $1,137