Abstract
3-Bromo-1-phenylprop-2-yn-1-one reacted with 1-benzylidenethiocarbonohydrazones in acetic acid or acetonitrile at room temperature (reaction time 3 h) to give in good yields the corresponding benzaldehyde N′-(5-benzoylmethyl-1,3,4-thiadiazol-2-yl)hydrazone hydrobromides which were converted into the free bases by treatment with aqueous ammonia.
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Blumenkopf, T.A., Harrington, J.A., Koble, C.S., Bankston, D.D., Morrison, R.W., Bigham, E.C., Jr., Styles, V.L., and Spector, T., J. Med. Chem., 1992, vol. 35, p. 2306.
Dimmock, J.R., Kumar, P., Allen, T.M., Kao, G.Y., Halleran, S., Balzarini, J., and De Clercq, E., Pharmazie, 1997, vol. 52, p. 182.
Naik, A.D., Annigeri, S.M., Gangadharmath, U.B., Revankar, V.K., and Mahale, V.B., J. Inclusion Phenom. Macrocyclic Chem., 2002, vol. 43, p. 291.
Abu-Hussen, A.A.A. and Emara, A.A.A., J. Coord. Chem., 2004, vol. 57, p. 973.
Bacchi, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez-Arguelles, M.C., Rogolino, D., Solinas, C., and Zani, F., J. Inorg. Biochem., 2005, vol. 99, p. 397.
Bacchi, A., Bonini, A., Carcelli, M., Ferraro, F., Leporati, E., Pelizzi, C., and Pelizzi, G., J. Chem. Soc., Dalton Trans., 1996, p. 2699.
Moubaraki, B., Murray, K.S., Ranford, J.D., Wang, X., and Xu, Y., Chem. Commun., 1998, p. 353.
Cheng, H., Chun-ying, D., Chen-jie, F., Yong-jiang, L., and Qing-jin, M., J. Chem. Soc., Dalton Trans., 2000, p. 1207.
Komarova, T.N., Nakhmanovich, A.S., Glotova, T.E., and Lopyrev, V.A., Izv. Ross. Akad. Nauk, Ser. Khim., 1998, p. 2083.
Dvorko, M.Yu., Albanov, A.I., Chipanina, N.N., Sherstyannikova, L.V., Samoilov, V.G., Komarova, T.N., and Glotova, T.E., Khim. Geterotsikl. Soedin., 2006, p. 1655.
Miller, S.I., Orzech, C.E., Welch, C.A., Ziegler, G.R., and Dickstein, J.I., J. Am. Chem. Soc., 1962, vol. 84, p. 2020.
Bax, A. and Subramanian, S., J. Magn. Reson., 1986, vol. 67, p. 565.
Bax, A. and Summers, M.F., J. Am. Chem. Soc., 1986, vol. 108, p. 2093.
Glotova, T.E., Nakhmanovich, A.S., Komarova, T.N., and Sigalov, M.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1988, p. 2637.
Nakhmanovich, A.S., Glotova, T.E., Komarova, T.N., Sigalov, M.V., and Romanenko, L.S., Khim. Geterotsikl. Soedin., 1990, p. 1421.
Glotova, T.E., Aleksandrova, A.E., Nakhmanovich, A.S., and Vinogradova, T.I., Khim.-Farm. Zh., 1990, vol. 24, no. 11, p. 48.
Song, Y., Connor, D.T., Sercel, A.D., Sorenson, R.J., Doubleday, R., Unangst, P.C., Roth, B.D., Beylin, V.G., Gilbertsen, R.B., Chan, K., Schrier, D.J., Guglietta, A., Bornemeier, D.A., and Dyer, R.D., J. Med. Chem., 1999, vol. 42, p. 1161.
Zou, X.J., Jin, G.Y., and Zhang, Z.X., J. Agric. Food Chem., 2002, vol. 50, p. 1451.
Wilton-Ely, J.D.E.T., Schier, A., and Schmidbaur, H., Organometallics, 2001, vol. 20, p. 1895.
Huang, Z., Du, M., Song, H.-B., and Bu, X.-H., Cryst. Growth Des., 2004, vol. 4, p. 71.
Huang, Z., Song, H.-B., Du, M., Chen, S.-T., and Bu, X.-H., Inorg. Chem., 2004, vol. 43, p. 931.
Bentiss, F., Lagrenee, M., Mentre, O., Conflant, P., Vezin, H., Wignacourt, J.P., and Holt, E.M., Inorg. Chem., 2004, vol. 43, p. 1865.
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Original Russian Text © T.E. Glotova, M.Yu. Dvorko, V.G. Samoilov, I.A. Ushakov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 875–878.
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Glotova, T.E., Dvorko, M.Y., Samoilov, V.G. et al. New 1,3,4-thiadiazole derivatives from 1-benzylidenethiocarbonohydrazides and 3-Bromo-1-phenylprop-2-yn-1-one. Russ J Org Chem 44, 866–869 (2008). https://doi.org/10.1134/S1070428008060158
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DOI: https://doi.org/10.1134/S1070428008060158