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Cycloaddition of azodicarboxylic acid esters to vinylpyridines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of methyl or ethyl esters of azodicarboxylic acid with 3-, 4-, 5-, or 6-alkyl-2-vinylpyridines proceeds via the scheme of the diene synthesis with the participation of the pseuodcarbodiene system of vinylpyridines and leads to the formation of 1,2,3,4-tetrahydro-5-azacinnoline derivatives. In addition to these “monoadducts,” 4-[N,N′-bis(methoxycarbonyl)hydrazino] derivatives are formed in large amounts., The structures of all of the reaction products were proved by the IR, UV, PMR, and mass spectra. The possibility of the application of the computational methods of MO perturbation theory for the prediction of the probability of the formation of various regioisomers is demonstrated.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    P. B. Terent'ev, V. G. Kartsev, I. K. Yakushenko, L. N. Prostakova, A. N. Kost & I. P. Gloriozov

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  1. P. B. Terent'ev
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  2. V. G. Kartsev
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  3. I. K. Yakushenko
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  4. L. N. Prostakova
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  5. A. N. Kost
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  6. I. P. Gloriozov
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 639–647, May, 1979.

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Terent'ev, P.B., Kartsev, V.G., Yakushenko, I.K. et al. Cycloaddition of azodicarboxylic acid esters to vinylpyridines. Chem Heterocycl Compd 15, 518–526 (1979). https://doi.org/10.1007/BF00773218

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  • DOI: https://doi.org/10.1007/BF00773218

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