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Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones

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Chemistry of Heterocyclic Compounds Aims and scope

An efficient one-pot method for the synthesis of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones in high yields has been developed via regioselective tandem reaction of coumarin-3-thioamides and ketones containing different methylene groups. Further oxidation with hydrogen peroxide under basic conditions leads to the formation of N-unsubstituted derivatives of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocin-4-one.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV-1006, Latvia

    Alexander V. Borisov

  2. Enamine Ltd., 23 Alexandra Matrosova St., Kyiv, 01103, Ukraine

    Alexander V. Borisov

  3. National University of Pharmacy, 53 Pushkinska St., Kharkiv, 61002, Ukraine

    Svitlana S. Kovalenko

  4. V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine

    Sergiy M. Kovalenko

Authors
  1. Alexander V. Borisov
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  2. Svitlana S. Kovalenko
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  3. Sergiy M. Kovalenko
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Correspondence to Alexander V. Borisov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(7), 678–681

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Borisov, A.V., Kovalenko, S.S. & Kovalenko, S.M. Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones. Chem Heterocycl Comp 51, 678–681 (2015). https://doi.org/10.1007/s10593-015-1756-8

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  • DOI: https://doi.org/10.1007/s10593-015-1756-8

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