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One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines

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Chemistry of Heterocyclic Compounds Aims and scope

A one-pot method for the synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes was developed on the basis of Rh2(esp)2-catalyzed reaction of diazoesters with 3-aryl-2-(pyridin-2-yl)-2H-azirines. To prevent deactivation of the catalyst with the pyridine-containing azirine reactant, the trimethylsilyl protection of pyridine nitrogen was used. The insertion and removal of the protecting group were carried out as a onepot synthesis. Reactions involving ethyl 2-diazo-3,3,3-trifluoropropanoate proceed stereoselectively with the formation of only the (2RS,3SR)-isomer of the dihydroazete, which is due to the thermodynamic control of the process.

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This work was supported by the Russian Science Foundation (project № 17-13-01078).

The analysis of synthesized compounds and quantumchemical calculations were carried out using the “Magnetic Resonance Research Center”, “Chemical Analysis and Materials Research Center”, “Chemistry Educational Center”, and “Computing Center” resource centers of Saint Petersburg State University.

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Authors and Affiliations

  1. Institute of Chemistry, Saint Petersburg State University, 7/9 University nab., Saint Petersburg, 199034, Russia

    Alexander N. Koronatov, Nikolai V. Rostovskii, Alexander F. Khlebnikov & Mikhail S. Novikov

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  1. Alexander N. Koronatov
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  2. Nikolai V. Rostovskii
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  3. Alexander F. Khlebnikov
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  4. Mikhail S. Novikov
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Correspondence to Mikhail S. Novikov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(12), 1185–1189

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Koronatov, A.N., Rostovskii, N.V., Khlebnikov, A.F. et al. One-pot synthesis of 3-(pyridin-2-yl)-2,3-dihydroazetes via Rh(II)-catalyzed reaction of diazoesters with trimethylsilyl-protected 2-(pyridin-2-yl)-2H-azirines. Chem Heterocycl Comp 55, 1185–1189 (2019). https://doi.org/10.1007/s10593-019-02599-y

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  • DOI: https://doi.org/10.1007/s10593-019-02599-y

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