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Synthesis of the E and Z isomers of 3-(5-aryl-1,3,4-oxadiazol-2-yl)acrylic acids

Abstract

Two procedures have been proposed for the synthesis of pure (E)- and (Z)-3-(5-aryl-1,3,4-oxadiazol-2-yl)acrylic acids, by one-step cyclization of (Z)-4-(2-aroylhydrazinyl)-4-oxobut-2-enoic acids or via initial cyclization of (Z)-4-(2-aroylhydrazinyl)-4-oxobut-2-enoic acids to 5-(aroylhydrazinylidene)furan-2(5H)-ones which are then converted into the target compounds.

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Correspondence to S. S. Rozhkov.

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Original Russian Text © S.S. Rozhkov, K.L. Ovchinnikov, G.G. Krasovskaya, A.S. Danilova, A.V. Kolobov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 7, pp. 1000–1005.

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Rozhkov, S.S., Ovchinnikov, K.L., Krasovskaya, G.G. et al. Synthesis of the E and Z isomers of 3-(5-aryl-1,3,4-oxadiazol-2-yl)acrylic acids. Russ J Org Chem 51, 982–987 (2015). https://doi.org/10.1134/S1070428015070155

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Keywords

  • Acrylic Acid
  • Maleic Anhydride
  • Ethyl Chloroformate
  • Hydrazinyl
  • Phosphoryl Chloride