Lemon Juice as a Natural Biodegradable Catalyst for an Ecofriendly One-Pot Pseudo-Three-Component Synthesis of N,1-Dimethyl-6-(methylsulfanyl)-3,5-dinitro-1,4-dihydropyridine-2-amines

Abstract

A one-pot pseudo-three-component reaction strategy has been designed for synthesizing all-carbon-functionalized hexasubstituted N,1-dimethyl-6-(methylsulfanyl)-3,5-dinitro-1,4-dihydropyridine-2-amines under neat conditions using inexpensive, readily available, natural, biodegradable lemon juice as a catalyst. The acidic reaction environment induced by lemon juice provided a superior catalytic performance, with a high reaction rate and high product yields, to those of a pool of Lewis and Brønsted acid catalysts. The wide substrate scope and functional-group tolerance permitted diversity creation with electronic and structural variations in a robust and operationally simple manner. The recoverability/reusability of the lemon juice catalyst and the easy purification of the end products by precipitation/filtration avoid the need for column chromatography or hazardous organic solvents and confirm that this is an environmentally benign sustainable technology. Moreover, a gram-scale operation and chemical modifications of the final products demonstrated some promising advantages.

Key words

1,4-dihydropyridines - acid catalyst - solvent-free reaction - green chemistry - lemon juice

Publication History

Received: 05 October 2024

Accepted after revision: 09 December 2024

Accepted Manuscript online:
09 December 2024

Article published online:
15 January 2025

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