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Regioselective addition of cyclic nitrones to Feist’s acid dimethyl ester

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Abstract

Cyclic nitrones, viz., tetrahydropyridine 1-oxide, 3,4-dihydroisoquinoline 2-oxide, and 2-methoxycarbonyl-4,5-dihydro-3H-pyrrole 1-oxide, regioselectively add to dimethyl 3-methylidenecyclopropane-1,2-dicarboxylate to form 5-spirocyclopropaneisoxazolidines. The latter undergo isomerization upon heating to give the corresponding tetrahydropyridin-4-ols and enaminones.

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Authors and Affiliations

  1. Department of Chemistry, St. Petersburg State University, 26 Universitetsky prosp., 198504, St. Petersburg, Russian Federation

    A. P. Molchanov, T. Q. Tran & R. R. Kostikov

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  1. A. P. Molchanov
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  2. T. Q. Tran
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  3. R. R. Kostikov
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Correspondence to R. R. Kostikov.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2253–2256, November, 2011.

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Molchanov, A.P., Tran, T.Q. & Kostikov, R.R. Regioselective addition of cyclic nitrones to Feist’s acid dimethyl ester. Russ Chem Bull 60, 2296–2300 (2011). https://doi.org/10.1007/s11172-011-0351-0

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  • DOI: https://doi.org/10.1007/s11172-011-0351-0

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