M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, K. A. Karpenko, V. M. Kalashnikova, M. P. Egorov, “An expedient cyclization of polyfunctional (aryl)(pyrimidinyl)(pyranyl)methanes into spiro[furo[3,2-<i>c</i>]pyran-2,5’-pyrimidine] scaffold”, Mendeleev Commun., 2023, Volume 33, Issue 4,Pages <nobr>448

This article is cited in 3 papers

Communications

An expedient cyclization of polyfunctional (aryl)(pyrimidinyl)(pyranyl)methanes into spiro[furo[3,2-c]pyran-2,5’-pyrimidine] scaffold

M. N. Elinson^a, A. N. Vereshchagin^b, Yu. E. Ryzhkova^a, K. A. Karpenko^a, V. M. Kalashnikova^ab, M. P. Egorov^a

^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation

Abstract: Spirocyclization of morpholinium 3-[(aryl)(1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)methyl]-6-methyl-2-oxo-2H-pyran-4-olate by the action of sodium acetate-N-bromosuccinimide system in ethanol at room temperature results in spiro[furo[3,2-c]pyran-2,5’-pyrimidine] derivatives in 92–98% yields, the protocol allowing to avoid column chromatography purification. This new highly efficient and facile procedure is a convenient way to substituted unsymmetrical spiro scaffold containing pyrimidine-2,4,6-trione and 2,3-dihydro-4H-furo[3,2-c]pyran-4-one fragments promising for biomedical applications.

Keywords: cyclization, base-oxidant system, sodium acetate, N-bromosuccinimide, morpholinium salts, furo[3,2-c]pyrans, spiro[furo- [3,2-c]pyran-2,5’-pyrimidine], pyranones, pyrimidine-2,4,6-triones.

Language: English

DOI: 10.1016/j.mencom.2023.06.002

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