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Synthesis of Benzo[1,4]thiazines via Ring Expansion of 2-Aminobenzothiazoles with Terminal Alkynes Under Metal–Organic Framework Catalysis

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Abstract

Copper–organic framework Cu–MOF-74 was synthesized, and consequently utilized as a heterogeneous catalyst for the synthesis of benzo[1,4]thiazines via ring expansion of 2-aminobenzothiazoles with terminal alkynes. Different from previous works, the reaction proceeded readily in the presence of lower catalyst concentration, at lower temperature, and under ligand-free conditions. The combination of 5 mol% framework catalyst, 20 mol% Cs2CO3, and 3 equivalents of di-tert-butyl peroxide led to high yields of benzo[1,4]thiazines. This copper-based framework demonstrated higher catalytic efficiency than a series of MOF-based heterogeneous catalysts and traditional homogeneous catalysts. In this system, the donation of soluble active copper species to the formation of benzo[1,4]thiazines was trivial. The copper–organic framework was reutilized without a remarkable decline in catalytic efficiency. To our best knowledge, this ring expansion reaction was not previously performed with a recyclable catalyst.

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Acknowledgements

We would like to thank the Viet Nam National Foundation for Science and Technology Development (NAFOSTED) for financial support under Project code 104.05-2017.32.

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Authors and Affiliations

  1. Faculty of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam

    Ha V. Dang, Y. T. N. Le, Duyen T. M. Tran, Anh N. Q. Phan & Nam T. S. Phan

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  1. Ha V. Dang
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  2. Y. T. N. Le
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  3. Duyen T. M. Tran
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Correspondence to Nam T. S. Phan.

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Dang, H.V., Le, Y.T.N., Tran, D.T.M. et al. Synthesis of Benzo[1,4]thiazines via Ring Expansion of 2-Aminobenzothiazoles with Terminal Alkynes Under Metal–Organic Framework Catalysis. Catal Lett 148, 1383–1395 (2018). https://doi.org/10.1007/s10562-018-2358-8

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  • DOI: https://doi.org/10.1007/s10562-018-2358-8

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