1D AND 2D NMR STUDIES OF 2–(2–(BENZYLOXY)–3–METHOXYPHENYL)–1H–BENZIMIDAZOLE

https://doi.org/10.22146/ijc.21697

Mohammed Hadi Al–Douh(1*), Shafida Abd Hamid(2), Hasnah Osman(3)

(1) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang, Malaysia
(2) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang, Malaysia
(3) School of Chemical Sciences, Universiti Sains Malaysia (USM), Minden 11800, Pinang, Malaysia
(*) Corresponding Author

Abstract


The reaction of Benzyl o-vanillin 1 and o-phenylene diamine 2 in dichloromethane produced new benzimidazole, 3. The complete assignments of 3 were made using 1D and 2D NMR including COSY, HMQC and HMBC NMR in CDCl3 and acetone-d6. The coupling constants J are reported in Hertz, and the differences in the peak splittings using both solvents are discussed.


Keywords


1H NMR; 13C NMR; 2D NMR; Benzimidazole

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References

[1] Wright, J.B., 1951, Chem. Rev., 48, 397–541

[2] Hofmann, K., 1953, The Chemistry of Heterocyclic Compounds Imidazole and Its Derivatives Part I, Interscience, London, 247–324.

[3] Craigo, W.A., LeSueur, B.W. and Skibo, E.B., 1999, J. Med. Chem., 42, 3324–3333

[4] White, A.W., Curtin, N.J., Eastman, B.W., Golding, B.T., Hostomsky, Z., Kyle, S., Li, J., Maegley, K.A., Skalitzky, D.J., Webber, S.E., Yu, X.H. and Griffin, R.J., 2004, Bioorg. Med. Chem. Lett., 14, 2433–2437.

[5] Gudmundsson, K.S., Tidwell, J., Lippa, N., Koszalka, G.W., van Draanen, N., Ptak, R.G., Drach, J.C. and Townsend, L.B., 2000, J. Med. Chem., 43, 2464–2472

[6] Cheng, J., Xie, J. and Luo, X., 2005, Bioorg. Med. Chem. Lett., 15, 267–269.

[7] Townsend, L.B. and Revankav, G.R., 1970, Chem. Rev., 70, 389–438

[8] Trivedi, R., De, S.K. and Gibbs, R.A., 2006, J. Mol. Cata. A: Chem., 245, 8–11.

[9] Kim, J.S., Gatto, B., Yu, C., Liu, A., Liu, L.F. and LaVoie, E.J., 1996, J. Med. Chem., 39, 992–998

[10] Rangarajan, M., Kim, J.S., Sim, S.P., Liu, A., Liub, L.F. and LaVoiea, E.J., 2000, Bioorg. Med. Chem., 8, 2591–2600

[11] Mekapati, S.B. and Hansch, C., 2001, Bioorg. Med. Chem., 9, 2885–2893.

[12] Hong, S.Y., Chung, K.H., You, H.J., Choi, I.H., Chae, M.J., Han, J.Y., Jung, O.J., Kang, S.J. and Ryu, C.K., 2004, Bioorg. Med. Chem. Lett., 14, 2563–3566.

[13] Kopanska (n. Zastapilo), K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. and Bretner, M., 2004, Bioorg. Med. Chem., 12, 2617–2624.

[14] Ozden, S., Atabey, D., Yildiz, S. and Goker, H., 2005, Bioorg. Med. Chem., 13, 1587–1597

[15] Nezhad, A.K., Rad, M.N.S., Mohabatkar, H., Asraria, Z. and Hemmateenejada, B., 2005, Bioorg. Med. Chem., 13, 1931–1938

[16] Kazimierczuk, Z., Andrzejewska, M., Kaustova, J. and Klimesova, V., 2005, Eur. J. Med. Chem., 40, 203–208.

[17] Mavrova, A.T., Anichina, K.K., Vuchev, D.I., Tsenov, J.A., Kondeva, M.S. and Micheva, M.K., 2005, Bioorg. Med. Chem., 13, 5550–5559.

[18] Sondhi, S.M., Sharma, V.K., Verma, R.P., Singhal, N., Shukla, R., Raghubir, R. and Dubey, M.P., 1999, Synthesis, 5, 878–884

[19] Sondhi, S.M., Singh, N., Kumar, A., Lozach, O. and Meijer, L., 2006, Bioorg. Med. Chem., 14, 3758–3765.

[20] Roth, T., Morningstar, M.L., Boyer, P.L., Hughes, S.H., Bukheit, R.W. and Michejda, C.J., 1997, J. Med. Chem., 40, 4199–4207

[21] Porcari, A.R., Devivar, R.V., Kucera, L.S., Drach, J.C. and Townsend, L.B., 1999, J. Med. Chem., 41, 1251–1262

[22] Rao, A., Chimirri, A., Clercq, E.D., Monforte, A.M., Monforte, P., Pannecouque, C. and Zappala, M., 2002, Il Farmaco, 57, 819–823

[23] Rao, A., Chimirri, A., Ferro,S., Monforte, A.M., Monoforte, P. and Zappala, M., 2004, ARKIVOC, v, 147–155

[24] Rida, S.M., El–Hawash, S.A.M., Fahmy, H.T.Y., Hazzaa, A.A. and El–Meligy, M.M.M., 2006, Arch. Pharm. Res., 29, 826–833.

[25] Kumar, D., Jacob, M.R., Reynolds, M.B. and Kerwin, S.M., 2002, Bioorg. Med. Chem., 10, 3997–4004

[26] Demirayak, S., Mohsen, U.A. and Karaburun, A.C., 2002, Eur. J. Med. Chem., 37, 255–260

[27] Andrzejewska, M., Mulia, L.Y., Rivera, R.C., Tapia, A., Vilpo, L., Vilpo, J. and Kazimierczuk, Z., 2002, Eur. J. Med. Chem., 37, 973–978

[28] Kupchinsky, S., Centioni, S., Howard, T., Trzupek, J., Roller, S., Carnahan, V., Townes, H., Purnell, B., Price, C., Handl, H., Summerville, K., Johnson, K., Toth, J., Hudson, S., Kiakos, K., Hartley, J.A. and Lee, M., 2004, Bioorg. Med. Chem., 12, 6221–6236

[29] Huang, S.T., Hsei, I.J. and Chen, C., 2006, Bioorg. Med. Chem., 14, 6106–6119.

[30] Soto, S.E., Molina, R.V., Crespo, F.A., Galicia, J.V., Diaz, H.M., Piedra, M.T. and Vazquez, G.N., 2006, Life Science, 79, 430–435.

[31] Vazquez, G.N., Diaz, H.M., Crespo, F.A., Rivera, I.L., Molina, R.V., Muniz, O.M. and Soto, S.E., 2006, Bioorg. Med. Chem. Lett., 16, 4169–4173.

[32] Al–Douh, M.H., Hamid, S.A., Osman, H., Ng, S.L. and Fun, H.K., 2006, Acta Cryst. E, 62, o3954–o3956.

[33] Al–Douh, M.H., Hamid, S.A. and Osman, H., in preparation.

[34] Crystal data of 3: C21H18N2O2, Mr = 330.37, monoclinic, P21/c, a = 9.54170 (1), b = 18.4590 (3), c = 11.0653 (2) Å, b = 123.814 (1)o, V = 1619.27 (4) Å3, Z = 4, m = 0.088 mm–1, dx = 1.355 g cm–3, F(000) = 696, GOF = 1.062. A total of 54869 reflections were collected and 8446 are unique (Rint = 0.0539), R = 0.0501, wR = 0.1282 for 227 parameters and 8446 reflections (I > 2s (I)). Residual electron density extremes were 0.613 and –0.326 e Å–3. The intensity data was collected at 297 K on SMART APEX2 CCD area–detector diffractometer with graphite–monochromated MoKa radiation (0.71073 Å), q range 2.21 to 37.50o [38]. All absorption corrections were performed by using SADABS the multiscan program [38]. The structure was solved and refined by SHELXTL against F2[39]. The H atoms were refined as riding and the Uiso values were freely refined, they were placed in calculated positions, with C–H = 0.93–0.97 Å and N–H = 0.89 Å. The software was used SHELXTL [39] and PLATON [40]. These data can be obtained free of charge from International Union of Crystallography IUCr cv2101 or The Cambridge Crystallographic Data Centre CCDC 620951. Reference: (doi:10.1107/S160053680603251X).

[35] Bruker program 1D WIN–NMR (release 6. 0) and 2D WIN–NMR (release 6.1).

[36] Berger, S. and Braun, S., 2004, 200 and More NMR Experiments, A Practical Course, Wiley–VCH, Weinheim.

[37] Claramunt, R.M., Lopez, C. and Elguero, J., 2006, ARKIVOC, v, 5–11.

[38] APEX2 (Version 1.27), SAINT (Version 7.12A), and SADABS (Version 2004/1), 2005, Bruker AXS Inc., Madison, Wisconsin, USA.

[39] Sheldrick, G.M., SHELXTL. (Version 5.1), 1998, Program for the Solution of Crystal Structures, Bruker AXS Inc., Madison, Wisconsin, USA.

[40] Spek, A.L., 2003, J. Appl. Cryst., 36, 7–13.



DOI: https://doi.org/10.22146/ijc.21697

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