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Khaskel, Anamika, and Pranjit Barman. Heteroatom Chemistry 27.2 (2016): 114-120.
Benzyltrimethylammonium fluoride hydrate (BTMAFH) has emerged as an effective catalyst for the synthesis of Hantzsch 1,4-dihydropyridines (1,4-DHPs) and their subsequent oxidation to pyridines under solvent-free conditions. This study demonstrates its catalytic efficiency in promoting multicomponent reactions, offering a cost-effective and eco-friendly alternative to conventional methods.
In a typical synthesis, aldehydes, ethyl acetoacetate, and ammonium acetate react in the presence of 10 mol% BTMAFH at 70°C, leading to the formation of 1,4-DHPs in high yields. The reaction is monitored by thin-layer chromatography (TLC), and upon completion, the product is isolated through simple filtration and recrystallization from an ethanol-chloroform mixture (7:3). The use of BTMAFH enhances the reaction rate, eliminates the need for toxic solvents, and simplifies product isolation, making the process highly sustainable.
Beyond its role in 1,4-DHP synthesis, BTMAFH facilitates oxidation reactions, converting 1,4-DHPs into their corresponding pyridine derivatives with excellent efficiency. Given the pharmacological importance of pyridines and 1,4-DHPs in drug development, this solvent-free protocol presents a valuable advancement in green chemistry. The superior catalytic performance of BTMAFH underscores its potential as a versatile phase-transfer catalyst in organic synthesis, offering a streamlined and environmentally benign approach to heterocyclic compound preparation.
