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

作者: Yu. V. Tomilov , D. N. Platonov , G. P. Okonnishnikova , R. A. Novikov , N. V. Volchkov

DOI: 10.1007/S11172-012-0155-X

关键词: Multiple bondsHalideOrganic chemistryThermal decompositionChemistryMedicinal chemistryHalogenPropargylArylCycloaddition

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

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