Biomimetic Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiadazole via the Group Transfer of Tetrahydrofolate Models

Author(s): Xueshan Wen, Jianxin Chen, Yanqin Zhao, Xingmao Chang, Jiachun Ma, Wenjun Zheng

Journal Name: Current Organic Synthesis

Volume 11 , Issue 6 , 2014

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Graphical Abstract:


By an efficient biomimetic synthetic method, several novel 2-substituted benzimidazoles, benzoxazoles, and benzothiadazole were readily prepared in good yields under mild conditions with 2-substituted imidazolinium iodides as the tetrahydrofolate model compounds at the oxidation level of formate. The reaction is probably involved in a nucleophilic addition to the C=N bond at the imidazolinium ring, followed a 1,3-H migration at an imidazolidine intermediate and a salt elimination.

Keywords: Benzimidazole, benzoxazole, benzothiadazole, biomimetic synthesis, imidazolinium iodide, transfer reaction, tetrahydrofolate model.

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Article Details

Year: 2014
Published on: 23 October, 2014
Page: [911 - 915]
Pages: 5
DOI: 10.2174/1570179411666140708173654
Price: $65

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