Premium
Synthesis of Pyridines and Pyrazines Using an Intramolecular Hydroamination‐Based Reaction Sequence
Author(s) -
Rizk Toni,
Bilodeau Eric J.F.,
Beauchemin André M.
Publication year - 2009
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.200903922
Subject(s) - hydroamination , aromatization , intramolecular force , oxime , chemistry , annulation , isomerization , alkyne , sequence (biology) , combinatorial chemistry , organic chemistry , catalysis , biochemistry
A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). p ‐Toluenesulfonic acid (2 mol %) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redox‐neutral aromatization step to occur.