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One-pot synthesis of \(\upgamma \)-spiroiminolactones and \(\upgamma \)-dispiroiminolactones using \(\textit{N}{,}{} \textit{N}^{\prime }\)-disubstituted parabanic acid and thioparabanic acid derivatives

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Abstract

A direct entry and simple process for the synthesis of \(\upgamma \)-spiroiminolactones present in a large number of natural products has been developed. In the first step, the synthesis of parabanic acid derivatives was commenced from the reaction of \(\textit{N}{,}{} \textit{N}^{\prime }\)-disubstituted urea and thiourea with oxalyl chloride, then a three-component reaction was carried out with isocyanides, acetylenic esters, and \(\textit{N}{,}{} \textit{N}^{\prime }\)-disubstituted parabanic acid derivatives. The method allows the construction of a variety of \(\upgamma \)-spiroiminolactone structures in good to high yields starting from readily available precursors. It was found that in the case of \(\textit{N}{,}{} \textit{N}^{\prime }\)-diphenyl thioparabanic acid, additional products of \(\upgamma \)-dispiroiminolactones have been formed due to the higher electrophilicity of \(\upalpha \)-dicarbonyl groups. The structures were fully established using spectroscopic analysis NMR, IR, and Mass spectrometry. The crystal structure of \(\upgamma \)-dispiroiminolactone was confirmed from single-crystal X-ray diffraction study.

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Acknowledgments

We gratefully acknowledge the financial support from the Research Council of Mazandaran University.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447, Iran

    Sakineh Asghari & Amir Ali Sarmadi

  2. Nano and Biotechnology Research Group, University of Mazandaran, Babolsar, Iran

    Sakineh Asghari

  3. Department of biology, Garmsar Branch, Islamic Azad University, Garmsar, Iran

    Mohammad Qandalee

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Correspondence to Sakineh Asghari.

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Asghari, S., Qandalee, M. & Sarmadi, A.A. One-pot synthesis of \(\upgamma \)-spiroiminolactones and \(\upgamma \)-dispiroiminolactones using \(\textit{N}{,}{} \textit{N}^{\prime }\)-disubstituted parabanic acid and thioparabanic acid derivatives. Mol Divers 21, 69–79 (2017). https://doi.org/10.1007/s11030-016-9698-3

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