The reaction of 2-R1-9-R2-imidazo[1,2-a]benzimidazoles with propiolic acid in polyphosphoric acid yields substituted 3-(9H-imidazo[1,2-a]benzimidazol-3-yl)acrylic acids. Their esterification reaction has been studied for the preparation of potentially biologically active compounds.
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V. A. Anisimova, I. E. Tolpygin, A. A. Spasov, T. S. Serdyuk, and A. G. Sukhov, Bioorg. Khim., 37, 836 (2011). [Russ. J. Bioorg. Chem., 37, 758 (2011)].
J. P. D. van Veldhoven, C. C. Blad, C. M. Artsen, C. Klopman, D. R. Wolfram, M. J. Abdelkadir, J. R. Lane, J. Brussee, and A. P. Ijzerman, Biol. Med. Chem. Lett., 21, 2736 (2011).
C. D. Haffner, J. M. Lenhard, A. B. Miller, D. L. McDougald, K. Dwornik, O. R. Ittoop, R. T. Gampe, Jr., H. E. Xu, S. Blanchard, V. G. Montana, T. G. Consler, R. K. Bledsoe, A. Ayscue, and D. Croom, J. Med. Chem., 47, 2010 (2004).
R. Cincinelli, S. Dallavalle, R. Nannei, S. Carella, D. De Zani, L. Merlini, S. Penco, E. Garattini, G. Giannini, C. Pisano, L. Vesci, P. Carminati, V. Zuco, C. Zanchi, and F. Zunino, J. Med. Chem., 48, 4931 (2005).
S. Hibi, Y. Okamoto, K. Tagami, H. Numata, N. Kobayashi, M. Shinoda, T. Kawahara, K. Harada, K. Miyamoto, and I. Yamatsu, J. Med. Chem., 39, 3148 (1996).
D. S. Millan, R. H. Prager, C. Brand, and P. H. Hart, Tetrahedron, 56, 811 (2000).
G. Kavanagh, J. Crosby, and M. Norval, Br. J. Dermatol., 133, 728 (1995).
S. D. Kumar and J. S. Sandhu, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 50B, 1479 (2011).
Y. Akita, T. Noguchi, M. Sugimoto, and A. Ohta, J. Heterocycl. Chem., 23, 1481 (1986).
J. Koubachi, S. Berteina-Raboin, A. Mouaddib, and G. Guillaumet, Synthesis, 271 (2009).
A. M. Simonov, V. A. Anisimova, and L. E. Grushina, Khim. Geterotsikl. Soedin., 838 (1970). [Chem. Heterocycl. Compd., 6, 778 (1970)].
V. A. Anisimova, N. I. Avdyunina, A. M. Simonov, G. V. Kovalev, and Yu. N. Simkina, Khim.-Farm. Zh., 12, No. 12, 40 (1978). [Pharm. Chem. J., 12, 1575 (1978)].
V. A. Anisimova, L. I. Zhurkina, and N. K. Chub, Khim. Geterotsikl. Soedin., 271 (1983). [Chem. Heterocycl. Compd., 19, 225 (1983)].
V. A. Anisimova, T. B. Korochina, and L. I. Zhurkina, Khim. Geterotsikl. Soedin., 1496 (1987). [Chem. Heterocycl. Compd., 23, 1195 (1987)].
A. M. Simonov and V. A. Anisimova, Khim. Geterotsikl. Soedin., 1102 (1968). [Chem. Heterocycl. Compd., 4, 801 (1968)].
A. M. Simonov and P. M. Kochergin, Khim. Geterotsikl. Soedin., 316 (1965). [Chem. Heterocycl. Compd., 1, 210 (1965)].
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*For Communication 30, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1379-1383, September, 2013.
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Anisimova, V.A., Tolpygin, I.E. & Borodkin, G.S. Studies of Imidazo[1,2-a]Benzimidazoles 31*. Synthesis of 3-(9H-Imidazo[1,2-a]Benz-Imidazol-3-yl)Acrylic Acids. Chem Heterocycl Comp 49, 1285–1288 (2013). https://doi.org/10.1007/s10593-013-1377-z
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DOI: https://doi.org/10.1007/s10593-013-1377-z