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


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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  1. Jiang, X., Liu, Y., Tian, H., Qiu, W., Song, X., and Zhu, D., J. Mater. Chem., 1997, 7, 1395.

    Article  CAS  Google Scholar 

  2. Nijegorodov, N. and Mabbs, R., Spectrochim. Acta, Part A, 2002, vol. 58, p. 349.

    Article  CAS  Google Scholar 

  3. Peng, Z., Bao, Z., and Galvin, M.E., Adv. Mater., 1998, vol. 10, p. 680.

    Article  CAS  Google Scholar 

  4. Jin, S.-Ho, Kim, M.-Y., Kim, J.Y., Lee, K., and Gal, Y.-S., J. Am. Chem. Soc., 2004, vol. 126, p. 2474.

    Article  CAS  Google Scholar 

  5. Zhang, Y., Zuniga, C., Kim, S.-J., Cai, D., Barlow, S., Salman, S., Coropceanu, V., Bredas, J.-L., Kippelen, B., and Marder, S., Chem. Mater., 2011, vol. 23, p. 4002.

    Article  CAS  Google Scholar 

  6. Akcelrud, L., Prog. Polymer. Sci., 2003, vol. 28, p. 875.

    Article  CAS  Google Scholar 

  7. Saegusa, Y., Koshikawa, T., and Nakamura, S., J. Polym. Sci., Part A: Polym. Chem., 1992, vol. 30, p. 1369.

    Article  CAS  Google Scholar 

  8. Detert, H. and Schollmeier, D., Synthesis, 1999, p. 999.

    Google Scholar 

  9. Gutov, O.V., Cryst. Growth Des., 2013, vol. 13, p. 3953.

    Article  CAS  Google Scholar 

  10. Le Berre, A., Godin, J., and Garreau, R., C.R. Acad. Sci., Ser. C, 1967, vol. 265, p. 570.

    CAS  Google Scholar 

  11. Siegrist, A.E., Moergeli, E., and Hoelzle, K., US Patent no. 2 765 304, 1956.

  12. Kolotova, N.V., Koz’minykh, E.N., Kolla, V.E., Syropyatov, B.Ya., Voronina, E.V., and Koz’minykh, V.O., Pharm. Chem. J., 1999, vol. 33, no. 5, p. 248.

    Article  CAS  Google Scholar 

  13. Structure Determination of Organic Compounds: Tables of Spectral Data, Pretsch, E., Bühlmann, P., and Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed. Translated under the title Opredelenie stroeniya organicheskikh soedinenii. Tablitsy spektral’nykh dannykh, Moscow: Mir, 2006, p. 174.

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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).

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