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Isothiourea‐Mediated One‐Pot Synthesis of Functionalized Pyridines
Author(s) -
Stark Daniel G.,
Morrill Louis C.,
Yeh PeiPei,
Slawin Alexandra M. Z.,
O'Riordan Timothy J. C.,
Smith Andrew D.
Publication year - 2013
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.201306786
Subject(s) - chemistry , thiophenol , sulfonyl , michael reaction , intermolecular force , combinatorial chemistry , polar effect , acetic acid , catalysis , organic chemistry , molecule , alkyl
Acids to bases : The synthesis of 2,4,6‐trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β‐unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N‐ to O‐sulfonyl migration, giving 2‐sulfonate‐substituted pyridines which are readily derivatized to generate structural diversity.