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Activated 2-methylidene-1,3-thiazolidin-4-ones in a promising approach to the synthesis of polyfunctional thiazolo[3,2-c]pyrimidines

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Abstract

A preparatively convenient and efficient synthetic route to new 5H-[1,3]thiazolo[3,2-c]pyrimidine derivatives is described which involves the cyclocondensation of acyl or alkoxycarbonyl α-functionalized 2-methylidene-1,3-thiazolidin-4-ones with 1-chlorobenzyl isocyanates. The optimal reaction conditions, viz., heating reagents in toluene in the absence of an organic base, afford the target products in 48–74% yields. Some tert-butyl 2-(4-oxo-1,3-thiazolidin-2-ylidene)ethanoates produce, along with the desired tert-butyl [1,3] thiazolo[3,2-c]pyrimidine-8-carboxylates, the corresponding 8-carboxylic acids in 18–21% yields. A reliable structural determination of all the synthesized compounds has been performed by elemental analysis and a number of spectroscopic methods (1H and 13C NMR, HPLC/MS, and FT-IR) as well as by X-ray diffraction analysis.

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Acknowledgements

We are grateful to the National Academy of Science of Ukraine for supporting this study under groups of young scientists of the NAS of Ukraine Grant (Grant number: 19/02-2021(3)).

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Mariia B. Litvinchuk, Anton V. Bentya, Eduard B. Rusanov & Mykhailo V. Vovk

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  1. Mariia B. Litvinchuk
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  2. Anton V. Bentya
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  3. Eduard B. Rusanov
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  4. Mykhailo V. Vovk
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Correspondence to Mariia B. Litvinchuk.

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Litvinchuk, M.B., Bentya, A.V., Rusanov, E.B. et al. Activated 2-methylidene-1,3-thiazolidin-4-ones in a promising approach to the synthesis of polyfunctional thiazolo[3,2-c]pyrimidines. Monatsh Chem 152, 1261–1268 (2021). https://doi.org/10.1007/s00706-021-02840-5

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  • DOI: https://doi.org/10.1007/s00706-021-02840-5

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