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1-Isopropyl-3-tert-butyl-1,2-diaza-1,3-butadiene in [4 + 2]-cycloaddition reactions

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1-Isopropyl-3-tert-butyl-1,2-diaza-1,3-butadiene (I), which is formed as a result of the reaction of α-chloropinacoline with isopropyl hydrazine, exists in the form of a mixture of cisoid and transold conformations and is extremely active in the diene synthesis with maleic anhydride, maleimide, dimethyl fumarate, and methyl vinyl ketone. The conformations of the derivatives obtained, which contain a Δ2-tetrahydropyridazine ring, were established on the basis of the PMR spectra. 1-Isopropyl-3-tert-butyl-trans-5,6-dicarbomethoxy-Δ2-tetrahydropyrid-azine was obtained from dimethyl fumarate and I; this was confirmed by a comparison of data on it with the characteristics of the cis isomer, synthesized by the action of diazomethane on the anhydride of 1-isopropyl-3-tert-butyl-Δ2-tetrahydropyridazine-5,6-dicarboxylic acid.

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Authors and Affiliations

  1. S. M. Kirov Military Medical Academy, Leningrad

    K. N. Zelenin, V. A. Nikitin & N. M. Anodina

Authors
  1. K. N. Zelenin
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  2. V. A. Nikitin
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  3. N. M. Anodina
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 124–128, January, 1973.

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Zelenin, K.N., Nikitin, V.A. & Anodina, N.M. 1-Isopropyl-3-tert-butyl-1,2-diaza-1,3-butadiene in [4 + 2]-cycloaddition reactions. Chem Heterocycl Compd 9, 112–116 (1973). https://doi.org/10.1007/BF00476166

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  • DOI: https://doi.org/10.1007/BF00476166

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