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Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement

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Chemistry of Heterocyclic Compounds Aims and scope

Rh2(OAc)4-catalyzed Wolff rearrangement of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate gave methoxycarbonyl(4-methoxyphenyl) ketene that was added to 2Н-azirines, resulting in opening of the three-membered ring at the N–C(2) bond and leading to the formation of 3,4-dihydro-2Н-pyrrol-2-one derivatives. Depending on the structure of the obtained products, they isomerized to the more stable 1Н-pyrrol-2(3H)-one derivatives or added a water molecule at the C=N bond.

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This work was performed with financial support from the Russian Science Foundation (project No. 17-13-01078). The analysis of obtained compounds was performed at the Saint Petersburg State University resource centers “Magnetic Resonance Research Centre” and “Chemical Analysis and Materials Research Centre”.

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Authors and Affiliations

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

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

  2. Durham University, South Road, Durham, DH1 3LE, United Kingdom

    Dmitry S. Yufit

Authors
  1. Nikolai V. Rostovskii
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  2. Mikhail S. Novikov
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  3. Alexander F. Khlebnikov
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  4. Dmitry S. Yufit
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Correspondence to Mikhail S. Novikov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(9), 985–988

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Rostovskii, N.V., Novikov, M.S., Khlebnikov, A.F. et al. Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement. Chem Heterocycl Comp 53, 985–988 (2017). https://doi.org/10.1007/s10593-017-2160-3

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  • DOI: https://doi.org/10.1007/s10593-017-2160-3

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