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An unusual synthesis of 3-(2-(arylamino)thiazol-4-yl)-2H-chromen-2-ones from ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylate via benzopyran ring opening

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Abstract

An unusual and unexpected synthesis of 3-(2-(arylamino)thiazol-4-yl)-2H-chromen-2-ones has been observed by the reaction of ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylate with various arylthioureas in ethanol under mild reaction conditions with excellent yields. The ambiguity in the structure of the obtained products has been solved by recording its single-crystal X-ray analysis. This protocol has been found to be a novel approach for the preparation of title compounds via benzopyran ring opening. A systematic plausible mechanism has been proposed for the formation of the product. Also, an efficient one-pot three-component method has been demonstrated for the formation of title compounds starting from salicylaldehyde.

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Acknowledgements

The authors are thankful to the authorities of Jawaharlal Nehru Technological University Hyderabad for providing laboratory facilities. One of the authors (KK) is thankful to the University for financial support in the form of Lectureship.

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Authors and Affiliations

  1. Department of Chemistry, College of Engineering, Jawaharlal Nehru Technological University, Hyderabad, Kukatpally, Hyderabad, Telangana, 500 085, India

    Kotthireddy Kavitha, Devulapally Srikrishna & Pasula Aparna

  2. Center for X-Ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, 500 007, India

    Balasubramanian Sridhar

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  1. Kotthireddy Kavitha
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Correspondence to Kotthireddy Kavitha.

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Kavitha, K., Srikrishna, D., Sridhar, B. et al. An unusual synthesis of 3-(2-(arylamino)thiazol-4-yl)-2H-chromen-2-ones from ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylate via benzopyran ring opening. Mol Divers 23, 443–452 (2019). https://doi.org/10.1007/s11030-018-9880-x

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