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Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid

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Chemistry of Heterocyclic Compounds Aims and scope

The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system.

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Notes

  1. Calculated relative to the consumed starting compound.

  2. Calculated relative to the consumed starting compound.

  3. Calculated relative to the consumed starting compound.

  4. Calculated relative to the consumed starting compound.

  5. Calculated relative to the consumed starting compound.

  6. Calculated relative to the consumed starting compound.

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Authors and Affiliations

  1. K. L. Khetagurov North-Ossetian State University, 46 Vatutina St., Vladikavkaz, 362040, Russia

    R. A. Gazzaeva & A. Z. Kadzhaeva

  2. M. V. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119992, Russia

    E. V. Trofimova, A. N. Fedotov & S. S. Mochalov

Authors
  1. R. A. Gazzaeva
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  2. E. V. Trofimova
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  3. A. Z. Kadzhaeva
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  4. A. N. Fedotov
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  5. S. S. Mochalov
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Corresponding authors

Correspondence to R. A. Gazzaeva or S. S. Mochalov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1309-1317, August, 2012.

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Gazzaeva, R.A., Trofimova, E.V., Kadzhaeva, A.Z. et al. Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid. Chem Heterocycl Comp 48, 1220–1227 (2012). https://doi.org/10.1007/s10593-012-1125-9

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  • DOI: https://doi.org/10.1007/s10593-012-1125-9

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