Monatshefte für Chemie - Chemical Monthly ( IF 1.7 ) Pub Date : 2021-09-05 , DOI: 10.1007/s00706-021-02840-5 Mariia B. Litvinchuk 1 , Anton V. Bentya 1 , Eduard B. Rusanov 1 , Mykhailo V. Vovk 1
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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
中文翻译：
活化的 2-methylidene-1,3-thiazolidin-4-ones 是合成多功能噻唑并 [3,2-c] 嘧啶的一种有前景的方法
描述了一种制备新的 5 H- [1,3]噻唑并[3,2- c ]嘧啶衍生物的方便有效的合成路线，它涉及酰基或烷氧羰基α-官能化的2-亚甲基-1,3-噻唑啉- 4-ones 与 1-氯苄基异氰酸酯。最佳反应条件，即在没有有机碱的情况下在甲苯中加热试剂，以 48-74% 的产率提供目标产物。一些叔丁基 2-(4-oxo-1,3-thiazolidin-2-ylidene) ethanoates 与所需的叔丁基 [1,3] 噻唑并 [3,2- c]嘧啶-8-羧酸盐，相应的8-羧酸的产率为18-21%。已通过元素分析和多种光谱方法（1 H 和13 C NMR、HPLC/MS 和 FT-IR）以及 X 射线衍射分析对所有合成化合物进行了可靠的结构测定。
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