Synthesis of 4-substituted 3,5-dinitro-1,4-dihydropyridines by the self-condensation of β-formyl-β-nitroenamine

Yumi Nakaike, Nagatoshi Nishiwaki*, Masahiro Ariga, Yoshito Tobe

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

3,5-Dinitro-1,4-dihydropyridines (DNDHPs) are readily constructed by the acid-promoted self-condensation of β-formyl-β-nitroenamines. In the DNDHPs, one molecule of the nitroenamine serves as a C3N1 building block and the other serves as a C2 block. This synthetic method does not require any special reagents and conditions. When the reaction is conducted in the presence of electron-rich benzene derivatives, arylation at the 4-position of DNDHP is achieved by trapping the 3,5-dinitropyridinium ion intermediate.

Original languageEnglish
Pages (from-to)2163-2169
Number of pages7
JournalJournal of Organic Chemistry
Volume79
Issue number5
DOIs
StatePublished - 7 Mar 2014

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