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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 5, pp 595–605 | Cite as

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

  • A. Z. Kadzhaeva
  • E. V. Trofimova
  • A. N. FedotovEmail author
  • K. A. Potekhin
  • R. A. Gazzaeva
  • S. S. Mochalov
  • N. S. Zefirov
Article

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.

Keywords

5-aryl-3-ethoxycarbonyl-4,5-dihydroisoxazoles 5-aryl-3-ethoxycarbonylisoxazoles ethyl esters of 2-arylcyclopropanecarboxylic acids insertion of the nitrosyl cation into the cyclopropane ring 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • A. Z. Kadzhaeva
    • 1
  • E. V. Trofimova
    • 2
  • A. N. Fedotov
    • 2
    Email author
  • K. A. Potekhin
    • 2
  • R. A. Gazzaeva
    • 1
  • S. S. Mochalov
    • 2
  • N. S. Zefirov
    • 2
  1. 1.K. L. Hetagurov North-Ossetian State UniversityVladikavkazNorth OssetiaRussia
  2. 2.M. V. Lomonosov Moscow State UniversityMoscowRussia

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