- Electrochemical synthesis of 1,2,4-triazole-fused heterocycles
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A reagent-free intramolecular dehydrogenative C-N cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram scale easily. This novel method was applied to the synthesis of one of the top-selling drugs Xanax and late stage functionalization for generating chemical diversity in biologically relevant lead molecules.
- Ye, Zenghui,Ding, Mingruo,Wu, Yanqi,Li, Yong,Hua, Wenkai,Zhang, Fengzhi
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supporting information
p. 1732 - 1737
(2018/04/30)
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- Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles [1]
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Gas-phase pyrolysis of N-arylidine-N′-pyrimidin-2-yl-hydrazine derivatives 1a, 1b, 1c, 1d, 1e gave the corresponding arylnitriles 2a, 2b, 2c, 2d, 2e, 2-aminopyrimidine 3, 3-phenyl-1,2,4-triazolo[4,3-a]pyrimidines 4, 2-phenyl-1,2,4-triazolo[1,5-a]pyrimidines 5, 2,4,5-triphenyl-1H-imidazole 6, and 2,3-diphenylquinoline 7. The analyses of the reaction products are reported and used to elucidate the mechanism of the pyrolytic process.
- Al-Awadi, Sundus A.,Ibrahim, Maher R.,El-Dusouqui, Osman M. E.,Al-Awadi, Nouria A.
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p. 1812 - 1816
(2015/11/09)
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