Synthesis of Pyridines and Pyrazines Using an Intramolecular Hydroamination‐Based Reaction Sequence | Zendy

Rizk Toni | Zendy; Bilodeau Eric J.F. | Zendy; Beauchemin André M. | Zendy

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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.

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