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SYNTHESIS OF SPIROCYCLIC PYRROLIZIDINEOXYINDOLES WITH A FUROTROPYLIDENE FRAGMENT BY 1,3-DIPOLAR CYCLOADDITION

А. В. Ткачук, С. В. Курбатов, О. Н. Буров, М. Е. Клецкий, П. Г. Морозов, В. И. Минкин
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Abstract


The 1,3-dipolar cycloaddition of the unstabilized azomethine ylides generated in situ from isatin and proline to the endocyclic C=C bond of the tropylidene ring is absolutely regio- and diastereoselective. The local electrophilicity of the dipolarophile and the local nucleophilicity of the azomethine ylide calculated by the B3LYP/6-31G** method are useful tools for predicting the regioselectivity of cycloaddition. The structure and the three-dimensional structure of the synthesized spiropyrrolizidineoxyindoles were established by correlation NMR spectroscopy and X-ray structural analysis.

How to Cite
Tkachuk, A. V.; Kurbatov, S. V.; Burov, O. N.; Kletskii, M. E.; Morozov, P. G.; Minkin, V. I. Chem. Heterocycl. Compd. 2014, 50, 26. [Khim. Geterotsikl. Soedin. 2014, 32.]

For this article in the English edition see DOI 10.1007/s10593-014-1444-0


Keywords


azomethine ylide; furotropone; isatin; spirooxyindole; spiropyrrolizidine; 1,3-dipolar cycloaddition; DFT (B3LYP/6-31G**); nucleophilic substitution

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