Facile One‐Pot Synthesis of [1, 2, 3]Triazolo[1, 5‐a]Pyridines from 2‐Acylpyridines by Copper(II)‐Catalyzed Oxidative NN Bond Formation |
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Authors: | Dr Tasuku Hirayama Dr Satoshi Ueda Takahiro Okada Norihiko Tsurue Prof Kensuke Okuda Prof Hideko Nagasawa |
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Institution: | Laboratory of Medicinal and Pharmaceutical Chemistry, Gifu Pharmaceutical University, 1‐25‐4, Daigaku‐nishi, Gifu 501‐1196 (Japan), Fax: (+81)?58‐230‐8112 |
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Abstract: | An efficient and simple method for the synthesis of various 1, 2, 3]triazolo1, 5‐a]pyridines has been established. The method involves a copper(II)‐catalyzed oxidative N?N 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 N?N 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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Keywords: | copper cyclizations hydrazones nitrogen heterocycles N N coupling |
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