Synthesis of Polysubstituted Dihydropyridines by Four-Component Reactions of Aromatic Aldehydes, Malononitrile, Arylamines, and Acetylenedicarboxylate

Abstract

A practical and efficient procedure for the preparation of the polysubstituted dihydropyridines was developed through a unique four-component reaction of aromatic aldehydes, malononitrile, arylamines, and acetylenedicarboxylate in ethanol in the presence of triethylamine as a base promoter. This four-component reaction is atom-efficient, high-yielding, and applicable to a wide variety of four-component reactions.

Efficient Synthesis of the Functionalized Spiro[indoline‐3,4′‐pyridine] via Four‐component Reaction

“…[5][6][7][8][9] In the past few years the multicomponent reactions based on the versatile reactivity of isatins have become the most widely used efficient methods for the synthesis of various spirooxindoles. [26] Recently Balalaie and coworkers also reported this four-compoenent reaction for the synthesis of 1,4-dihydropyridines by using (NH 4 ) 2 HPO 4 as a base in aqueous media. We found that the four-component reactions of aromatic aldehydes, arylamines, acetylenedicarboxylate and acetonitrile derivatives provided an efficient method for the preparation of the polysubstituted 1,4-dihydropyridines.…”

Fe3O4@SiO2-NH2 Nanocomposite as a Robust and Effective Catalyst for the One-pot Synthesis of Polysubstituted Dihydropyridines

“…[12][13][14] It is likely that NH 2 groups on the surfaces of nanoparticles act as a Brønsted base and cause the dehydrogenation of substrates. …”

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

“…It is known that the formation of β - enamino ester by the reaction of arylamine with methyl propiolate requires a relative long time [38–42]. Thus, under our previously established reaction conditions a molar excess of p -toludine (4.0 mmol) and methyl propiolate (2.0 mmol) reacted in ethanol at room temperature overnight to give the desired β - enamino ester.…”