Issue 0, 1979

Heterodiene syntheses. Part 20. 4-Arylidene-5-pyrazolones and ynamines : a [2 + 2]cycloaddition followed by electrocyclic ring opening, in competition with a [4 + 2]cycloaddition; the influence of the substituents on the intermediate

Abstract

4-Arylidene-5-pyrazolones (1) react with NN-diethylaminomethylacetylene to give a mixture of pyrano[2,3-c]pyrazoles (3), in accordance with a [4 + 2]cycloaddition, and 4-(3-aryl-1-diethylamino-2-methylpropenylidene)pyrazol-5-ones (5) which are formed by electrocyclic ring opening of the [2 + 2]cycloadducts (4). The configuration of the open-chain compounds (5) permits the deduction of that of the originally formed cyclobutene adducts. The reason for the choice between a [4 + 2] and a [2 + 2] cycloaddition can be rationalized in terms of the effect of both the substituents and the configuration of the substrate.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 856-862

Heterodiene syntheses. Part 20. 4-Arylidene-5-pyrazolones and ynamines : a [2 + 2]cycloaddition followed by electrocyclic ring opening, in competition with a [4 + 2]cycloaddition; the influence of the substituents on the intermediate

G. Desimoni, P. Righetti, G. Tacconi and R. Oberti, J. Chem. Soc., Perkin Trans. 1, 1979, 856 DOI: 10.1039/P19790000856

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