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Reactions of 4-phenyl-1,2,4-triazoline-3,5-dione with 2-pyrazolines

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Abstract

4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) acts as an efficient Michael acceptor in reactions with 1-unsubstituted 2-pyrazolines, giving substituted (3,5-dioxo-4-phenyl-1,2,4-triazol-idin-1-yl)-1-pyrazolines in quantitative yields. Through elimination of molecular nitrogen, the latter are easily transformed into the corresponding cyclopropanes. A reaction of methyl 5-methyl-2-pyrazoline-5-carboxylate with a twofold excess of PTAD leads to an intermediate bisadduct, which undergoes dediazotization to form a 1,3,5-triazabicyclo[3.3.0]octane-2,4-dione derivative. 1-Substituted 2-pyrazolines also add to PTAD with the exception that the 2-pyrazoline structure is retained in the product because of the migration of the C(3)H proton to PTAD.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    R. A. Novikov, V. A. Korolev & Yu. V. Tomilov

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  1. R. A. Novikov
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  2. V. A. Korolev
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  3. Yu. V. Tomilov
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Correspondence to Yu. V. Tomilov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1660–1668, August, 2011.

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Novikov, R.A., Korolev, V.A. & Tomilov, Y.V. Reactions of 4-phenyl-1,2,4-triazoline-3,5-dione with 2-pyrazolines. Russ Chem Bull 60, 1685–1693 (2011). https://doi.org/10.1007/s11172-011-0252-2

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  • DOI: https://doi.org/10.1007/s11172-011-0252-2

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