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Chemistry of iminofurans: XI. Synthesis, structure, and cyclization of 4-substituted 2-(aroylhydrazinylidene)-4-oxobutanoic acids

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Abstract

Aromatic hydrazides reacted with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl- 4-oxohex-2-enoic acids to give 4-aryl-2-(2-aroylhydrazinylidene)-4-oxobutanoic and 5,5-dimethyl-2-(aroylhydrazinylidene)- 4-oxohexanoic acids. The products were found to exist in solution as mixtures of Z/E-hydrazinylidene and cyclic dihydropyrazole tautomers, and they underwent intramolecular cyclization to 5-aryland 5-tert-butyl-3-(aroylhydrazinylidene)furan-2(3H)-ones by the action of acetic anhydride.

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, ul. Polevaya 2, Perm, 614990, Russia

    N. M. Igidov & M. A. Kiselev

  2. Perm State National Research University, ul. Bukireva 15, Perm, 614990, Russia

    A. E. Rubtsov

Authors
  1. N. M. Igidov
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  2. M. A. Kiselev
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  3. A. E. Rubtsov
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Correspondence to A. E. Rubtsov.

Additional information

Original Russian Text © N.M. Igidov, M.A. Kiselev, A.E. Rubtsov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 4, pp. 540–546.

For communication X, see [1].

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Igidov, N.M., Kiselev, M.A. & Rubtsov, A.E. Chemistry of iminofurans: XI. Synthesis, structure, and cyclization of 4-substituted 2-(aroylhydrazinylidene)-4-oxobutanoic acids. Russ J Org Chem 52, 526–532 (2016). https://doi.org/10.1134/S1070428016040084

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