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Construction of 3,5-dinitrated 1,4-dihydropyridines modifiable at 1,4-positions by a reaction of β-formyl-β-nitroenamines with aldehydes†
Mai Hamada,Yumi Nakaike
RSC Advances Pub Date : 10/16/2015 00:00:00 , DOI:10.1039/C5RA19439C
Abstract

A novel and efficient method for the synthesis of 4-substituted 3,5-dinitro-1,4-dihydropyridines by a reaction of β-formyl-β-nitroenamines with aldehydes was developed. The reaction of nitroenamines with aldehydes leading to 1,4-dihydropyridines and the self-condensation of nitroenamines leading to pyridinium salt intermediate proceed competitively. The obtained 3,4,5-trisubstituted-1,4-dihydropyridines readily transformed into the corresponding pyridines in high yields.

Graphical abstract: Construction of 3,5-dinitrated 1,4-dihydropyridines modifiable at 1,4-positions by a reaction of β-formyl-β-nitroenamines with aldehydes
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