Generation of 1-aryl-3-methoxycarbonylnitrilimines and their reaction with halogen-containing unsaturated compounds |
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Authors: | Yu. V. Tomilov D. N. Platonov G. P. Okonnishnikova R. A. Novikov N. V. Volchkov |
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Affiliation: | 1155. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
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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. |
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