Synthesis of 4‑Substituted 3,5-Dinitro-1,4-dihydropyridines by the Self-Condensation of β‑Formyl-β-nitroenamine

Synthesis of 4‑Substituted 3,5-Dinitro-1,4-dihydropyridines by the Self-Condensation of β‑Formyl-β-nitroenamine

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...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 79; no. 5; pp. 2163 - 2169
Main Authors: Nakaike, Yumi, Nishiwaki, Nagatoshi, Ariga, Masahiro, Tobe, Yoshito
Format: Journal Article
Language:English
Published: United States American Chemical Society 07-03-2014
Online Access:Get full text
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Summary: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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo5000187