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A three-component, one-pot synthesis of 1,8-naphthyridine and isoxazole derivatives and computational elucidation of the mechanism

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Abstract

An efficient and general method for the synthesis of substituted 3,4-dimethylisoxazolo[5,4-b]pyridine-5-carboxamide and benzo[b][1,8]naphthyridine-3-carboxamide derivatives by using 2,2,6-trimethyl-4H-1,3-dioxin-4-one, benzyl amine, aromatic aldehydes, 2-aminoquinoline, or 5-amino-3-methylisoxazole in the presence of a catalytic amount of p-toluenesulfonic acid or iodine is described. The formation of the products was investigated and the results obtained were also supported by theoretical calculations.

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Acknowledgements

N. Ocal gratefully acknowledges financial support of this work by the Scientific and Technological Research Council of Turkey (TUBITAK, project no. 112T880). I. Erden acknowledges financial support of this work by funds from the National Institutes of Health (grant no. SC1GM082340). The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

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Authors and Affiliations

  1. Faculty of Arts and Sciences, Department of Chemistry, Yildiz Technical University, Davutpasa Campus, 34220, Esenler-Istanbul, Turkey

    Muge Guleli & Nuket Ocal

  2. Faculty of Arts and Sciences, Chemistry Department, Marmara University, 34722, Goztepe, Istanbul, Turkey

    Safiye S. Erdem

  3. Department of Chemistry and Biochemistry, San Francisco State University, 1600 Holloway Avenue, San Francisco, CA, 94132, USA

    Ihsan Erden

  4. Department of Chemistry, Kırsehir Ahi Evran University, 40100, Kırsehir, Turkey

    Ozlem Sari

Authors
  1. Muge Guleli
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  2. Safiye S. Erdem
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  3. Nuket Ocal
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  4. Ihsan Erden
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  5. Ozlem Sari
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Corresponding authors

Correspondence to Safiye S. Erdem, Nuket Ocal or Ihsan Erden.

Additional information

This paper is dedicated to Prof. Nuket Ocal. During the revision process of this manuscript, our dear colleague and friend, Prof. Nuket Ocal, tragically passed away. We are deeply grateful to Dr. Ocal’s tireless efforts, dedication and her—and her students’—invaluable contributions to this project.

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Guleli, M., Erdem, S.S., Ocal, N. et al. A three-component, one-pot synthesis of 1,8-naphthyridine and isoxazole derivatives and computational elucidation of the mechanism. Res Chem Intermed 45, 2119–2134 (2019). https://doi.org/10.1007/s11164-018-03721-z

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  • DOI: https://doi.org/10.1007/s11164-018-03721-z

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