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SYNTHETIC TRANSFORMATIONS OF SESQUITERPENE LACTONES. 8. SYNTHESIS OF 13-(2-OXOFURO-[2,3-d]PYRIMIDIN-3(2H)-YL)EUDESMANOLIDES

С. С. Патрушев, М. М. Шакиров, Т. В. Рыбалова, Э. Э. Шульц
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Abstract


An aza-Michael reaction of isoalantolactone with 5-bromo- or 5-iodo-substituted uracils gave (11R)‑13-[5-bromo(iodo)-2,4-dioxotetrahydropyrimidin-1-yl]eudesma-4(15)-en-8β,12-olides, which were highly active in Pd-catalyzed cross-coupling reaction with terminal alkynes. Copper-catalyzed Mannich reaction of (11R)-13-(5-ethynyl-2,4-dioxotetrahydropyrimidin-1-yl)eudesma-4(15)-en-8β,12-olide with secondary amines and formaldehyde was used for the synthesis of (11R)-13-[5-(diethyl-amino)propynyl]-, (11R)-13-[5-(pyrrolidinyl-1-yl)propynyl]-, (11R)-13-[5-(4-oxopiperidin-1-yl)-propynyl]-, (11R)-13-[5-(4-methylpiperazin-1-yl)propynyl]-, and (11R)-13-(5-{[2-(pyridin-3-yl)piperidin-1-yl]propynyl}-2,4-dioxotetrahydropyrimidin-1-yl)eudesmanolides. The treatment of 13-[5(propargyl-amino)tetrahydropyrimidin-1-yl]eudesmanolides with silver nitrate led to the corresponding (11R)-13-(2-oxofuro[2,3-d]pyrimidin-3(2H)-yl)eudesmanolides. The structures of two compounds were proved by X‑ray structural analysis.

How to Cite
Patrushev, S. S.; Shakirov, M. M.; Rybalova, T. V.; Shults, E. E. Chem. Heterocycl. Compd. 2014, 50, 1063. [Khim. Geterotsikl. Soedin. 2014, 1155.]

For this article in the English edition see DOI 10.1007/s10593-014-1566-4


Keywords


isoalantolactone; uracils; aza-Michael reaction; copper-catalyzed Mannich reaction; cross coupling; silver-catalyzed cyclization reaction

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