Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides

Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2014, Volume: 50, Number: 8, Pages: 1063-1080 Pages count : DOI: 10.1007/s10593-014-1566-4

Tags

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

Authors

Patrushev S. S. ¹ , Shakirov M. M. ¹ , Rybalova T. V. ¹ , Shults E. E. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

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-8 beta,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-8 beta,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.

Patrushev S.S. , Shakirov M.M. , Rybalova T.V. , Shults E.E.
Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides
Chemistry of Heterocyclic Compounds. 2014. V.50. N8. P.1063-1080. DOI: 10.1007/s10593-014-1566-4 WOS Scopus РИНЦ

Published online:	Oct 8, 2014
Published print:	Nov 1, 2014

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