Premium
One‐Pot Synthesis of Tri‐ and Tetrasubstituted Pyridines by Sequential Ring‐Opening/Cyclization/Oxidation of N‐Arylmethyl 3‐Aziridinylpropiolate Esters
Author(s) -
Yoshida Masahiro,
Mizuguchi Tomotaka,
Namba Kosuke
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201409015
Subject(s) - phosphine , chemistry , ring (chemistry) , combinatorial chemistry , medicinal chemistry , catalysis , reaction conditions , organic chemistry
A novel strategy for the one‐pot synthesis of substituted pyridines from N‐arylmethyl 3‐aziridinylpropiolate esters is described. The method employs a three‐step procedure including the formation of allenyl imines, phosphine‐catalyzed cyclization, and subsequent oxidation of the dihydropyridines. Depending on the reaction conditions of the final oxidation step, tri‐ and tetrasubstituted pyridines can be selectively produced.