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

Yumi Nakaike | Zendy; Nagatoshi Nishiwaki | Zendy; Masahiro Ariga | Zendy; Yoshito Tobe | Zendy

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

Author(s) -

Yumi Nakaike,

Nagatoshi Nishiwaki,

Masahiro Ariga,

Yoshito Tobe

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo5000187

Subject(s) - condensation , reagent , chemistry , benzene , block (permutation group theory) , combinatorial chemistry , molecule , medicinal chemistry , organic chemistry , mathematics , physics , combinatorics , thermodynamics

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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