4.6 Article

Facile One-Pot Synthesis of [1,2,3] Triazolo[ 1, 5-a] Pyridines from 2Acylpyridines by Copper(II)-Catalyzed Oxidative N-N Bond Formation

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 14, Pages 4156-4162

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302997

Keywords

copper; cyclizations; hydrazones; nitrogen heterocycles; NN coupling

Funding

  1. Japan Society for the Promotion of Science (JSPS) [23750195]
  2. Grants-in-Aid for Scientific Research [25702050, 23750195] Funding Source: KAKEN

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An efficient and simple method for the synthesis of various [1,2,3]triazolo[1,5-a]pyridines has been established. The method involves a copper(II)-catalyzed oxidative NN bond formation that uses atmospheric oxygen as the terminal oxidant following hydrazonation in one pot. The use of ethyl acetate as the solvent dramatically promotes the oxidative NN bond-formation reaction and enables the application of oxidative cyclization in the efficient one-pot reaction. A mechanism for the reaction was proposed on the basis of the results of a spectroscopic study.

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