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Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Esters of 2-arylcyclopropanecarboxylic acids react with nitrous acid generated in situ with regioselective insertion of the nitrosyl cation into the cyclopropane ring. Depending on the substrate/nitrosylating agent ratio, the reaction proceeds with the formation of either aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles or the corresponding isoxazoles. The nature and position of the substituents in the aromatic ring of the starting 2-arylcyclopropanecarboxylic acid esters affect the reaction rate but have no effect on the regioselectivity of the attack by the nitrosyl cation on the three-membered ring. A dependence of the reactivity of isomeric substrates on their stereochemistry and position of the nitro group in the aromatic ring is noted for 2- and 4-nitrophenyl derivatives of esters of cis- and trans-2-arylcyclopropanecarboxylic acids.

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Authors and Affiliations

  1. K. L. Hetagurov North-Ossetian State University, Vladikavkaz, 362040, North Ossetia, Russia

    A. Z. Kadzhaeva & R. A. Gazzaeva

  2. M. V. Lomonosov Moscow State University, Moscow, 119992, Russia

    E. V. Trofimova, A. N. Fedotov, K. A. Potekhin, S. S. Mochalov & N. S. Zefirov

Authors
  1. A. Z. Kadzhaeva
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  2. E. V. Trofimova
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  3. A. N. Fedotov
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  4. K. A. Potekhin
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  5. R. A. Gazzaeva
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  6. S. S. Mochalov
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  7. N. S. Zefirov
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Corresponding author

Correspondence to A. N. Fedotov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 753–765, May, 2009.

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Kadzhaeva, A.Z., Trofimova, E.V., Fedotov, A.N. et al. Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles. Chem Heterocycl Comp 45, 595–605 (2009). https://doi.org/10.1007/s10593-009-0315-6

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  • DOI: https://doi.org/10.1007/s10593-009-0315-6

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