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Synthesis of heterocyclic systems involving [3,3]-sigmatropic rearrangements

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Abstract

The review summarizes the data on the synthesis of heterocyclic compounds by means of [3,3]-sigmatropic transformations, which include the Fischer, Claisen, and Cope rearrangements, as well as their numerous variations. These reactions have proved to be a convenient and efficient method for the synthesis of complex and poorly available heterocyclic systems with several chiral centers due to the highly ordered transition state of the process. Methods for the construction of five- and six-membered and medium size oxygen-, nitrogen-, and sulfur- containing heterocycles are described, as well as their use in the synthesis of condensed systems and natural compounds.

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  1. Peoples’ Frendship University of Russia (RUDN University), 6 ul. Miklukho-Maklaya, 117198, Moscow, Russian Federation

    M. S. Kobzev, A. A. Titov & A. V. Varlamov

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  1. M. S. Kobzev
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1213–1259, July, 2021.

This work was financially supported by the Russian Foundation for Basic Research (Project No. 19-13-50451). The authors declare no competing interests.

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Kobzev, M.S., Titov, A.A. & Varlamov, A.V. Synthesis of heterocyclic systems involving [3,3]-sigmatropic rearrangements. Russ Chem Bull 70, 1213–1259 (2021). https://doi.org/10.1007/s11172-021-3208-1

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