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


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Article Info

DATE

2021-09-05

AUTHORS

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

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.Graphic abstract More... »

PAGES

1261-1268

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00706-021-02840-5

DOI

http://dx.doi.org/10.1007/s00706-021-02840-5

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1140899167


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