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

[ Vol. 11 , Issue. 6 ]

Author(s):

Xueshan Wen, Jianxin Chen, Yanqin Zhao, Xingmao Chang, Jiachun Ma and Wenjun Zheng   Pages 911 - 915 ( 5 )

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.

Affiliation:

College of Chemistry and Materials Science, Shanxi Normal University, Lin fen 041004, China.

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