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Diphosphorus Tetraiodide (P2I4): An Efficient Catalyst for Synthesis of 2-Aryl-1,3-benzazoles via Cyclocondensation of o-Amino/Mercaptan/Hydroxy Anilines with Aryl Acids
Corresponding Author(s) : Vikas N. Telvekar
Asian Journal of Chemistry,
Vol. 30 No. 2 (2018): Vol 30 Issue 2
Abstract
An efficient and versatile approach for the synthesis of 2-substituted 1,3-benzazoles has been developed via diphosphorus tetraiodide (P2I4) catalyzed condensation reaction of ortho-substituted anilines (–NH2, –SH and –OH) with various aromatic acids to give benzimidazoles, benzothiazoles and benzoxazoles in excellent yields. Additionally, the synthetic approach reported herein has advantages such as mild reaction conditions, broad substrate scopes as well as simple one-pot operation, common for all the three 1,3-benzazoles, which makes this strategy highly attractive.
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- M. Mader, A. de Dios, C. Shih, R. Bonjouklian, T. Li, W. White, B.L. de Uralde, C. Sánchez-Martinez, M. del Prado, C. Jaramillo, E. de Diego, L.M. Martín Cabrejas, C. Dominguez, C. Montero, T. Shepherd, R. Dally, J.E. Toth,A. Chatterjee, S. Pleite, J. Blanco-Urgoiti, L. Perez, M. Barberis, M.J. Lorite, E. Jambrina, C.R. Nevill Jr., P.A. Lee, R.C. Schultz, J.A. Wolos, L.C. Li, R.M. Campbell and B.D. Anderson, Bioorg. Med. Chem. Lett., 18, 179 (2008); https://doi.org/10.1016/j.bmcl.2007.10.106.
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References
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F. Arjmand, B. Mohani and S. Ahmad, Eur. J. Med. Chem., 40, 1103 (2005); https://doi.org/10.1016/j.ejmech.2005.05.005.
A.T. Mavrova, K.K. Anichina, D.I. Vuchev, J.A. Tsenov, P.S. Denkova, M.S. Kondeva and M.K. Micheva, Eur. J. Med. Chem., 41, 1412 (2006); https://doi.org/10.1016/j.ejmech.2006.07.005.
Y. Kohara, K. Kubo, E. Imamiya, T. Wada, Y. Inada and T. Naka, J. Med. Chem., 39, 5228 (1996); https://doi.org/10.1021/jm960547h.
F. Gualtieri, G. Brody, A.H. Fieldsteel and W.A. Skinner, J. Med. Chem., 15, 420 (1972); https://doi.org/10.1021/jm00274a026.
W.A. Denny, G.W. Rewcastle and B.C. Baguley, J. Med. Chem., 33, 814 (1990); https://doi.org/10.1021/jm00164a054.
G. Yadav and S. Ganguly, Eur. J. Med. Chem., 97, 419 (2015); https://doi.org/10.1016/j.ejmech.2014.11.053.
R.S. Keri, M.R. Patil, S.A. Patil and S. Budagumpi, Eur. J. Med. Chem., 89, 207 (2015); https://doi.org/10.1016/j.ejmech.2014.10.059.
J.B. Wright, Chem. Rev., 48, 397 (1951); https://doi.org/10.1021/cr60151a002.
Y. Riadi, R. Mamouni, R. Azzalou, M.E. Haddad, S. Routier, G. Guillaumet and S. Lazar, Tetrahedron Lett., 52, 3492 (2011); https://doi.org/10.1016/j.tetlet.2011.04.121.
H.M. Bachhav, S.B. Bhagat and V.N. Telvekar, Tetrahedron Lett., 52, 5697 (2011); https://doi.org/10.1016/j.tetlet.2011.08.105.
D.F. Shi, T.D. Bradshaw, S. Wrigley, C.J. McCall, P. Lelieveld, I. Fichtner and M.F.G. Stevens, J. Med. Chem., 39, 3375 (1996); https://doi.org/10.1021/jm9600959.
J.A. Seijas, M.P. Vazquez-Tato, M.R. Carballido-Reboredo, J. CrecenteCampo and L. Romar-Lopez, Synlett, 2007, 313 (2007); https://doi.org/10.1055/s-2007-967994.
X. Wen, J.E. Bakali, R. Deprez-Poulain and B. Deprez, Tetrahedron Lett., 53, 2440 (2012); https://doi.org/10.1016/j.tetlet.2012.03.007.
D.W. Hein, R.J. Alheim and J.J. Leavitt, J. Am. Chem. Soc., 79, 427 (1957); https://doi.org/10.1021/ja01559a053.
C.T. Brain and J.T. Steer, J. Org. Chem., 68, 6814 (2003); https://doi.org/10.1021/jo034824l.
Y.S. Su and C.M. Sun, Synlett, 1243 (2005); https://doi.org/10.1055/s-2005-865240.
A.J. Blacker, M.M. Farah, M.I. Hall, S.P. Marsden, O. Saidi and J.M.J. Williams, Org. Lett., 11, 2039 (2009); https://doi.org/10.1021/ol900557u.
Y.H. So and J.P. Heeschen, J. Org. Chem., 62, 3552 (1997); https://doi.org/10.1021/jo960441u.
Z.T. Fomum, P.D. Landor, S.R. Landor and G.B. Mpango, Tetrahedron Lett., 16, 1101 (1975); https://doi.org/10.1016/S0040-4039(00)72068-5.
Y. Kim, M.R. Kumar, N. Park, Y. Heo and S. Lee, J. Org. Chem., 76, 9577 (2011); https://doi.org/10.1021/jo2019416.
J. Peng, C. Zong, M. Ye, T. Chen, D. Gao, Y. Wang and C. Chen, Org. Biomol. Chem., 9, 1225 (2011); https://doi.org/10.1039/C0OB00454E.
A. Teimouri, A.N. Chermahini, H. Salavati and L. Ghorbanian, J. Mol. Catal. Chem., 373, 38 (2013); https://doi.org/10.1016/j.molcata.2013.02.030.