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

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

Volume: 11 Issue: 6

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

Affiliation:

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

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.

Cite this article as:

Wen Xueshan, Chen Jianxin, Zhao Yanqin, Chang Xingmao, Ma Jiachun and Zheng Wenjun, Biomimetic Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiadazole via the Group Transfer of Tetrahydrofolate Models, Current Organic Synthesis 2014; 11 (6) . https://dx.doi.org/10.2174/1570179411666140708173654