Синтез нових n,n´-дизаміщених 5-спіроциклопентен-3-іл 2,4,6 триоксогексагідропіримідинів

N. I. Kobyzhcha; V. M. Holovatiuk; Yu. V. Bezugly; V. I. Kashkovsky

doi:10.24959/ophcj.13.770

Authors

N. I. Kobyzhcha Institute of Bioorganic Chemistry and Petrochemistry of NAS of Ukraine, Ukraine
V. M. Holovatiuk Institute of Bioorganic Chemistry and Petrochemistry of NAS of Ukraine, Ukraine
Yu. V. Bezugly Institute of Bioorganic Chemistry and Petrochemistry of NAS of Ukraine, Ukraine
V. I. Kashkovsky Institute of Bioorganic Chemistry and Petrochemistry of NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.13.770

Keywords:

ring-closing methathesis (RCM), 5-spiro-2, 4, 6-trioxyhexahydropyrimidines, derivatives of tiolan-1, 1- dioxide, ruthenium сarbene catalysts

Abstract

The synthesis of new N, N`-disubtituted 5-spiro-2,4,6-trihydropyrimidinetriones by ring-closing metathesis reactions has been presented in this work. Starting compounds for obtaining of spirocycles (5,5-diallyl-1,1-dioxythiolanyl-2,4,6-trihydropyrimidinetriones) have been synthesized by two pathways, one of them is condensation of carbamides with malonic acid in the presence of dehydrating agents, whereas the other path consists in the condensation of dicyanodiamide with diallylcyanoacetic ester in the presence of sodium alkoxide, and the resulting products are subjected to alkylation with the following acid hydrolysis. It has been found that imidazolidine containing the isopropoxybenzylidene ruthenium complex is the most suitable for carrying out of ring-closing metathesis reactions since it has the high thermal stability; it allows to obtain the target products with a high yield due to carrying out these reactions at the higher temperatures. The preliminary computer prognosis of the biological activity of new 1,1-dioxythiolan derivatives with the help of PASS (Prediction of Activity Spectra for Substances) programme has shown that some of these compounds can be ATPase proteasome inhibitors. Moreover, new spirocyclopenten containing derivatives may be promissing as precursors for obtaining of biologically active substances.

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