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Properties of a multiple bond conjugated with the pyridine ring

X. Change in the orientation of the addition of diazomethane to the polarized multiple bond of substituted vinylpyridines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The products of the addition of diazomethane to the double bond of α-, β-, and γ-vinyl-pyridines, 2-propenyl-, 2-styryl-, and 2-(p-nitrostyryl)pyridines, and β-(2-pyridyl)acrylic acid were obtained. When a hydrogen atom or alkyl or phenyl group is present in the β-position of the vinyl group, 3-pyridyl-Δ2-pyrazolines are formed (they are isolated as the acetyl derivatives). Electron-acceptor substituents (COOCH3 and C6H4NO2) in this position disrupt the polarization, and this leads to the formation of a mixture of two isomeric pyrazolines. The primary formation of Δ1-pyrazolines was proved by means of IR and UV spectroscopy.

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See [1] for communication IX.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 64–69, January, 1973.

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Terent'ev, P.B., Vinogradova, S.M., Kost, A.N. et al. Properties of a multiple bond conjugated with the pyridine ring. Chem Heterocycl Compd 9, 55–59 (1973). https://doi.org/10.1007/BF00476150

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  • DOI: https://doi.org/10.1007/BF00476150

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