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Synthesis of Spirocyclic Pyrrolizidineoxyindoles with a Furotropylidene Fragment by 1,3-Dipolar Cycloaddition

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Southern Federal University, 7 Zorge St., Rostov-on-Don, 344090, Russia

    A. V. Tkachuk, S. V. Kurbatov, O. N. Burov, M. E. Kletskii, P. G. Morozov & V. I. Minkin

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  1. A. V. Tkachuk
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  2. S. V. Kurbatov
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  3. O. N. Burov
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  4. M. E. Kletskii
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  5. P. G. Morozov
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  6. V. I. Minkin
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Correspondence to A. V. Tkachuk.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 32-40, January, 2014.

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Tkachuk, A.V., Kurbatov, S.V., Burov, O.N. et al. Synthesis of Spirocyclic Pyrrolizidineoxyindoles with a Furotropylidene Fragment by 1,3-Dipolar Cycloaddition. Chem Heterocycl Comp 50, 26–34 (2014). https://doi.org/10.1007/s10593-014-1444-0

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  • DOI: https://doi.org/10.1007/s10593-014-1444-0

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