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Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis

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Abstract

Ethyl 3-(2,4-dioxocyclohexyl)propanoate has been explored as a precursor for the synthesis of N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones following conventional protecvtion, selective amidation, and deprotective-cyclization approaches. Moreover, a facile process for the selective dehydrogenative aromatization of these diones was developed to afford the corresponding N-substituted 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and N-substituted 7-hydroxyquinolin-2(1H)-ones under mild conditions.

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Acknowledgments

This study was supported by the Council of Scientific and Industrial Research (project ORIGIN-CSC0108). VT thanks the UGC, New Delhi for awarding fellowship. The authors also gratefully thank the Director CSIR-IHBT, Palampur for providing necessary facilities during the course of study.

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Authors and Affiliations

  1. Natural Product Chemistry and Process Development, CSIR-Institute of Himalayan Bioresource Technology, Palampur, H.P., 176061, India

    Vandna Thakur, Dharminder Sharma & Pralay Das

  2. Academy of Scientific & Innovative Research, New Delhi, India

    Vandna Thakur & Pralay Das

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  1. Vandna Thakur
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  2. Dharminder Sharma
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  3. Pralay Das
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Correspondence to Pralay Das.

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Thakur, V., Sharma, D. & Das, P. Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis. Mol Divers 20, 29–40 (2016). https://doi.org/10.1007/s11030-015-9643-x

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