Synthesis of Isoxazoline Derivatives Based on Nitrile Oxide Cycloaddition of Nitroso-Nitro-Enamine

Lászlõ András Kondacs, Mihály Viktor Pilipecz, Zoltán Mucsi, Barbara Balázs, Tamás Gáti, Miklõs Nyerges, András Dancsõ, Péter Nemes

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Abstract

A new and stable nitroso-nitro-enamine reagent, providing a nitrile oxide 1,3-dipole, has been treated with dipolarophiles in the course of 1,3-dipolar cycloaddition reactions to give a large number of novel isoxazolyl-pyrroline derivatives. Surprisingly, instead of the expected 2-isoxazolyl-dihydropyrrole cycloadducts, dihydropyrrol-3-one oximes were isolated as the main products in most cases. The imino-oxime moiety was successfully transformed into 3-aminopyrrole derivatives. The mechanism and selectivity of the reactions were also studied by experimental and theoretical methods [WB97XD/6-311++G(2d,2p)//B3LYP/6-311++G(2d,2p)], including the solvent effect. A new and stable nitroso-nitro-enamine reagent, providing a nitrile oxide 1,3-dipole, has been treated with dipolarophiles in the course of 1,3-dipolar cycloaddition reactions to give a large number of novel isoxazolyl-pyrrolines. The mechanism of the reactions has been studied by experimental and theoretical methods.

Original languageEnglish
Pages (from-to)6872-6890
Number of pages19
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number31
DOIs
Publication statusPublished - Nov 1 2015

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Keywords

  • Cycloaddition
  • Density functional calculations
  • Nitrile oxides
  • Nitrogen heterocycles
  • Oximes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Kondacs, L. A., Pilipecz, M. V., Mucsi, Z., Balázs, B., Gáti, T., Nyerges, M., Dancsõ, A., & Nemes, P. (2015). Synthesis of Isoxazoline Derivatives Based on Nitrile Oxide Cycloaddition of Nitroso-Nitro-Enamine. European Journal of Organic Chemistry, 2015(31), 6872-6890. https://doi.org/10.1002/ejoc.201500905