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Transition-metal-free synthesis of imidazobenzothiazines via domino C-S/C-N bond formation

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Abstract

The carbon-heteroatom bond formation is an important research field. Transition-metal-free synthesis of medicinally important heterocycles avoids products of transition metal contamination, and thus it is an environmentally friendly and cost-saving process. A transition-metal-free domino C-S/C-N formation for the synthesis of imidazobenzothiazines from 2-mercaptobenzimidazoles and 2-halobenzyl bromides is developed. The desired products were obtained in good to excellent yields. The mechanism of domino nucleophilic substitution (SN2) and nucleophilic aromatic substitution (SNAr) is proposed.

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Acknowledgments

We thank the National Natural Science Foundation of China (No. 21372034) and the cultivating program for excellent innovation team of Chengdu University of Technology.

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Authors and Affiliations

  1. Institute of Green Catalysis and Synthesis, College of Materials and Chemistry and Chemical Engineering, Chengdu University of Technology, Chengdu, 610059, China

    Xingzhao Tu, Lihong Zhou, Zhijie Li, Ning Lei & Qingle Zeng

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  1. Xingzhao Tu
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  2. Lihong Zhou
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  3. Zhijie Li
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  4. Ning Lei
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  5. Qingle Zeng
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Corresponding authors

Correspondence to Lihong Zhou or Qingle Zeng.

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Tu, X., Zhou, L., Li, Z. et al. Transition-metal-free synthesis of imidazobenzothiazines via domino C-S/C-N bond formation. Monatsh Chem 145, 1925–1931 (2014). https://doi.org/10.1007/s00706-014-1264-z

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  • DOI: https://doi.org/10.1007/s00706-014-1264-z

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