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Staudinger Reaction of Schiff Bases of Acetylthiophene and Acetylpyridine with Ketenes. Diastereoselective Synthesis of 4-Heterosubstituted β-Lactams and their Conversion to β-Thiolactams

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Summary.

Arylimines of 2-acetylthiophene and 2-, 3-, and 4-acetylpyridines react with ketenes yielding 4-heterosubstituted β-lactams. Reactions of imines with ketenes were proved to be diastereoselective. The stereochemistry of the products was confirmed by X-ray analysis. β-Lactams treated with Lawesson’s reagent gave β-thiolactams.

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Authors and Affiliations

  1. Department of Organic Chemistry, Jagiellonian University, Kraków, Poland

    Małgorzata Krasodomska

  2. Regional Laboratory of Physicochemical Analysis and Structural Research, Jagiellonian University, Kraków, Poland

    Paweł Serda

Authors
  1. Małgorzata Krasodomska
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  2. Paweł Serda
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Correspondence to Małgorzata Krasodomska.

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Krasodomska, M., Serda, P. Staudinger Reaction of Schiff Bases of Acetylthiophene and Acetylpyridine with Ketenes. Diastereoselective Synthesis of 4-Heterosubstituted β-Lactams and their Conversion to β-Thiolactams. Monatsh. Chem. 138, 199–204 (2007). https://doi.org/10.1007/s00706-007-0588-3

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  • DOI: https://doi.org/10.1007/s00706-007-0588-3

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