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 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.
Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University , Machikaneyama, Toyonaka, Osaka, 560-8531, Japan.
Yumi
Y
Nakaike
Nagatoshi
N
Nishiwaki
Masahiro
M
Ariga
Yoshito
Y
Tobe