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Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction

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Chemistry of Heterocyclic Compounds Aims and scope

Castagnoli–Cushman reaction of imines derived from 2-chloropyridine-3-carboxaldehyde with a cyclic anhydride (4-(methylsulfonyl)-morpholine-2,6-dione) conducted at 110°C in DMF over 1 h, as expected, led to a mixture of trans- and cis-configured carboxylic acids. However, the latter underwent a spontaneous intramolecular reaction of the carboxylic functionality onto the labile nearby 2-chloropyridine moiety to give the respective tricyclic lactones in 17–23% yield, along with 41–68% yield of the uncyclized trans-configured products (isolated as methyl esters).

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This research was supported by the Russian Science Foundation (project grant 14-50-00069).

NMR, mass spectrometry and X-ray diffraction studies were performed at the Research Center for Magnetic Resonance, the Center for Chemical Analysis and Materials Research and the Center for X-ray Diffraction Methods of Research park of Saint Petersburg State University.

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Authors and Affiliations

  1. Institute of Chemistry, Saint Petersburg State University, 26 Universitetskii Ave., Peterhof, 198504, Russia

    Liliia Usmanova, Olga Bakulina, Dmitry Dar’in & Mikhail Krasavin

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  1. Liliia Usmanova
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  2. Olga Bakulina
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  3. Dmitry Dar’in
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  4. Mikhail Krasavin
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Correspondence to Mikhail Krasavin.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(4), 474–479

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Usmanova, L., Bakulina, O., Dar’in, D. et al. Spontaneous formation of tricyclic lactones following the Castagnoli–Cushman reaction. Chem Heterocycl Comp 53, 474–479 (2017). https://doi.org/10.1007/s10593-017-2076-y

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  • DOI: https://doi.org/10.1007/s10593-017-2076-y

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