1,3-Dipolar cycloaddition reactions of 2-arylmethylidenthiazolo[3,2-a]pyrimidines with azomethinylides, studying the supramolecular organization of products in the crystalline phase.

Reactions of 1,3-dipolar cycloaddition are the focus of modern research due to the wide range of reagents and the simplicity of the reactions and, consequently, the great synthetic potential for both the development of fundamental chemical science and for the preparative and industrial production of practically significant compounds.

The [3+2]-cycloaddition of azomethinylides formed in situ to dipolarophiles is a promising method for the synthesis of dispyro derivatives of oxindole and acenaphthenedione. In the course of our studies, it was shown that the cycloaddition of azomethinylide occurs only through the exocyclic double C=C bond, which leads to the formation of a new pyrrolidine cycle as part of the molecule and, as a result, a dispyroheterocycle.

This work is devoted to the synthesis and study of the structure of 2-arylmethylidene derivatives and dispyrothiazolo[3,2-a]pyrimidine both in the solution and in the crystalline phase.

The unique property of supramolecular self-assembly of the condensation products of 2-arylmethylidenedithiazolo[3,2-a]pyrimidines with isatin and sarcosine is the formation of microporous material, which further allows the use of crystalline samples of these derivatives as potential absorbents.

Hence, the synthesis was successfully carried out and the structure of the obtained dispyrothiazolo[3,2-a]pyrimidine derivatives in the solution and in the solid phase was studied, and the possibility of creating microporous materials was discovered. The obtained derivatives were characterized by a complex of physico-chemical methods (IR, NMR-¹H and ¹³C spectroscopy, ESI-MS spectrometry, X-ray diffraction analysis).