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Russian Chemical Bulletin

, Volume 61, Issue 6, pp 1138–1147 | Cite as

Generation of 1-aryl-3-methoxycarbonylnitrilimines and their reaction with halogen-containing unsaturated compounds

  • Yu. V. Tomilov
  • D. N. Platonov
  • G. P. Okonnishnikova
  • R. A. Novikov
  • N. V. Volchkov
Full Articles

Abstract

Thermal decomposition of 1-(4-methoxyphenyl)- and 1-(4-fluorophenyl)hepta(methoxycarbonyl)-3a,7a-dihydroindazoles at 135 °C in the presence of allyl or propargyl halides leads to the elimination of hexamethyl benzenehexacarboxylate and the formation of the corresponding pyrazolines or pyrazoles as the products of 1,3-dipolar cycloaddition of 1-aryl-3-methoxycarbonylnitrilimines to the multiple bonds of the substrates used. In the case of vinyl halides, the products of the target reactions are either obtained in low yields or nonexistent, with a side conversions taking place instead. Thus, for example, in the case of 1,1-dichloro-4-methylpenta-1,3-diene, besides hexamethyl benzenehexacarboxylate, 3,5,5-trichloro-2-methylpent-4-en-2-ol and arylchlorohydrazones MeO2CC(Cl)=N-NHAr were unexpectedly isolated as the main products, as well.

Key words

3a,7a-dihydroindazoles nitrilimines pyrazolines pyrazoles hydrazones 1,3-dipolar addition thermolysis 

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Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • Yu. V. Tomilov
    • 1
  • D. N. Platonov
    • 1
  • G. P. Okonnishnikova
    • 1
  • R. A. Novikov
    • 1
  • N. V. Volchkov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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