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Synfacts 2010(1): 0021-0021
DOI: 10.1055/s-0029-1218467
DOI: 10.1055/s-0029-1218467
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Synthesis of 1,2,4-Triazoles
S. Ueda, H. Nagasawa*
Gifu Pharmaceutical University, Japan
Further Information
Publication History
Publication Date:
21 December 2009 (online)
Significance
Reported is the efficient copper-catalyzed synthesis of 1,2,4-triazoles 3 and 5 from amidines 1 or 2-aminopyridines 4 and nitriles 2. Both alkyl (1˚, 2˚, and 3˚) and aryl amidines are tolerated in this reaction with equal efficiency. One example of a 5-amino-1,2,4-triazole was also prepared from a guanidine precursor. A wide range of starting nitriles bearing EDG, EWG, and heterocycles may be used although, in general, electron-deficient nitriles gave higher yields than the electron-rich substrates. A mechanism involving the copper-promoted addition of the amine into the nitrile followed by oxidative cyclization is presented by analogy to related processes.