Open AccessSynthesis 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 -
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.