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An Efficient and Green Synthesis of Imidazoles Using Natural Organic Acids as Promoter under Solvent-Free Condition
Corresponding Author(s) : Limbraj R. Patil
Asian Journal of Chemistry,
Vol. 29 No. 8 (2017): Vol 29 Issue 8
Abstract
An efficient and eco-friendly synthesis of imidazoles, promoted by naturally occurring acids, via condensation of benzil, aldehyde and ammonium acetate using conventional and microwave heating under solvent-free condition is described. Reactions under microwave irradiation are faster and gave slightly higher yields against conventional heating.
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- P.T. Anastas and T.C. Williamson, Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Oxford Science Publications, New York (1998).
- A.S. Matlack, Introduction to Green Chemistry, Marcel Dekker, Inc., New York (2001).
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- J.M. DeSimone, Science, 297, 799 (2002); https://doi.org/10.1126/science.1069622.
- (a) S. Chandrasekhar and K. Gopalaiah, Tetrahedron Lett., 44, 7437 (2003); https://doi.org/10.1016/j.tetlet.2003.08.038.
- Suresh, A. Saini, D. Kumar and J.S. Sandhu, Green Chem. Lett. Rev., 2, 29 (2009); https://doi.org/10.1080/17518250902973833.
- A. de Vasconcelos, P.S. Oliveira, M. Ritter, R.A. Freitag, R.L. Romano, F.H. Quina, L. Pizzuti, C.M.P. Pereira, F.M. Stefanello and A.G. Barschak, J. Biochem. Mol. Toxicol., 26, 155 (2012); https://doi.org/10.1002/jbt.20424.
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- (a) F.F. Stephens and J.D. Bower, J. Chem. Soc., 2971 (1949); https://doi.org/10.1039/jr9490002971. (b) H. Chikashita, S. Nishida, M. Miyazaki, Y. Morita and K. Itoh, Bull. Chem. Soc. (Japan), 60, 737 (1987); https://doi.org/10.1246/bcsj.60.737. (c) S. Kumar, V. Kansal and A. Bhaduri, Indian J. Chem., 20B, 254 (1991); (d) F. Pätzold, F. Zeuner, T. Heyer and H.-J. Nielas, Synth. Commun., 22, 281 (1992); https://doi.org/10.1080/00397919208021304. (e) R.L. Lombardy, F.A. Tanious, K. Ramachandran, R.R. Tidwell and W.D. Wilson, J. Med. Chem., 39, 1452 (1996); https://doi.org/10.1021/jm9507946. (f) P.L. Beaulieu, B. Hache and E. von Moos, Synthesis, 1683 (2003); https://doi.org/10.1055/s-2003-40888.
- (a) Z.-H. Zhang, L. Yin and Y.-M. Wang, Catal. Commun., 8, 1126 (2007); https://doi.org/10.1016/j.catcom.2006.10.022. (b) Z.H. Zhang, L. Yin, Y. Li and Y.M. Wang, Tetrahedron Lett., 46, 889 (2005); https://doi.org/10.1016/j.tetlet.2004.11.161.
- (a) C. Chen and Y.J. Chen, Tetrahedron Lett., 45, 113 (2004); https://doi.org/10.1016/j.tetlet.2003.10.095. (b) J.P. Mayer, G.S. Lewis, C. McGee and D. Bankaitis-Davis, Tetrahedron Lett., 39, 6655 (1998); https://doi.org/10.1016/S0040-4039(98)01427-0.
- V. Sareen, U. Gupta, V. Khatri and S. Chug, Indian J. Heterocycl. Chem., 17, 355 (2008).
- S.A. Siddiqui, U.C. Narkhede, S.S. Palimbar, T. Danial, R.J. Lahoti and K.V. Srinivasan, Tetrahedron, 61, 3539 (2005); https://doi.org/10.1016/j.tet.2005.01.116.
- F.E. Hahn and M.C. Jahnke, Angew. Chem., 120, 3166 (2008); https://doi.org/10.1002/ange.200703883.
- M. Suzuki, S. Maeda and K. Matsumoto, Boll. Chim. Farm., 34, 3111 (1986).
- L. Almirante, A. Mugnaini, P. Rugarli, A. Gamba, E. Zefelippo, N.D. Toma and W. Murmann, J. Med. Chem., 12, 122 (1969); https://doi.org/10.1021/jm00301a031.
- F. Suzuki, T. Kuroda, T. Tamura, S. Sato, K. Ohmori and S. Ichikawa, J. Med. Chem., 35, 2863 (1992); https://doi.org/10.1021/jm00093a020.
References
P.T. Anastas and T.C. Williamson, Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes, Oxford Science Publications, New York (1998).
A.S. Matlack, Introduction to Green Chemistry, Marcel Dekker, Inc., New York (2001).
M. Poliakoff and P.T. Anastas, Nature, 413, 257 (2001); https://doi.org/10.1038/35095133.
J.M. DeSimone, Science, 297, 799 (2002); https://doi.org/10.1126/science.1069622.
(a) S. Chandrasekhar and K. Gopalaiah, Tetrahedron Lett., 44, 7437 (2003); https://doi.org/10.1016/j.tetlet.2003.08.038.
Suresh, A. Saini, D. Kumar and J.S. Sandhu, Green Chem. Lett. Rev., 2, 29 (2009); https://doi.org/10.1080/17518250902973833.
A. de Vasconcelos, P.S. Oliveira, M. Ritter, R.A. Freitag, R.L. Romano, F.H. Quina, L. Pizzuti, C.M.P. Pereira, F.M. Stefanello and A.G. Barschak, J. Biochem. Mol. Toxicol., 26, 155 (2012); https://doi.org/10.1002/jbt.20424.
(a) G.L. Gravatt, B.C. Baguley, W.R. Wilson and W.A. Denny, J. Med. Chem., 37, 4338 (1994); https://doi.org/10.1021/jm00051a010. (b) J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu and E.J. La Voie, J. Med. Chem., 39, 992 (1996); https://doi.org/10.1021/jm950412w. (c) T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); https://doi.org/10.1021/jm970096g. (d) D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003); https://doi.org/10.1021/cr020033s.
(b) B. Jayashankara and K.M. Lokanatha Rai, ARKIVOC, 75 (2008); https://doi.org/10.3998/ark.5550190.0009.b07. (c) T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit Jr. and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); https://doi.org/10.1021/jm970096g. (d) S.N. Lin and L.H. Yang, Tetrahedron Lett., 46, 4315 (2005); https://doi.org/10.1016/j.tetlet.2005.04.101. (e) J. Valdez, R. Cedillo, A. Hernandez-Campos, L. Yepez, F. Hernandez- Luis, G. Navarrete-Vazquez, A. Tapia, R. Cortes, M. Hernández and R. Castillo, Bioorg. Med. Chem. Lett., 12, 2221 (2002); https://doi.org/10.1016/S0960-894X(02)00346-3. (f) A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach and L.B. Townsend, J. Med. Chem., 41, 1252 (1998); https://doi.org/10.1021/jm970559i. (g) K.C. Ravindra, H.M. Vagdevi and V.P. Vaidya, ARKIVOC, 1 (2008); https://doi.org/10.3998/ark.5550190.0009.b01.
(a) C. Hubschwerlen, P. Pflieger, J.L. Specklin, K. Gubernator, H. Gmuender, P. Angehrn and I. Kompis, J. Med. Chem., 35, 1385 (1992); https://doi.org/10.1021/jm00086a006. (b) J.S. Kim, Q. Sun, B. Gatto, C. Yu, A. Liu, L.F. Liu and E.J. LaVoie, Bioorg. Med. Chem., 4, 621 (1996); https://doi.org/10.1016/0968-0896(96)00047-8. (c) 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.
(a) Y. He, J. Yang, B. Wu, L. Risen and E.E. Swayze, Bioorg. Med. Chem. Lett., 14, 1217 (2004); https://doi.org/10.1016/j.bmcl.2003.12.051. (b) I I. Yildiz-Oren, I. Yalcin, E. Aki-Sener and N. Ucarturk, Eur. J. Med. Chem., 39, 291 (2004); https://doi.org/10.1016/j.ejmech.2003.11.014. (c) J.M. Gardiner, C.R. Loyns, A. Burke, A. Khan and N. Mahmood, Bioorg. Med. Chem. Lett., 5, 1251 (1995); https://doi.org/10.1016/0960-894X(95)00203-6.
(a) Y. Bai, J. Lu, Z. Shi and B. Yang, Synlett, 544 (2001); https://doi.org/10.1055/s-2001-12339. (b) E. Hasegawa, A. Yoneoka, K. Suzuki, T. Kato, T. Kitazume and K. Yanagi, Tetrahedron, 55, 12957 (1999); https://doi.org/10.1016/S0040-4020(99)00804-2.
(a) R.W. Middleton and D.G. Wibberley, J. Heterocycl. Chem., 17, 1757 (1980); https://doi.org/10.1002/jhet.5570170824. (b) T. Hisano, M. Ichikawa, K. Tsumoto and M. Tasaki, Chem. Pharm. Bull. (Tokyo), 30, 2996 (1982); https://doi.org/10.1248/cpb.30.2996. (c) T.A. Fairley, R.R. Tidwell, I. Donkor, N.A. Naiman, K.A. Ohemeng, R.J. Lombardy, J.A. Bentley and M. Cory, J. Med. Chem., 36, 1746 (1993); https://doi.org/10.1021/jm00064a008. (d) A. Czarny, W.D. Wilson and D.W. Boykin, J. Heterocycl. Chem., 33, 1393 (1996); https://doi.org/10.1002/jhet.5570330463.
(a) F.F. Stephens and J.D. Bower, J. Chem. Soc., 2971 (1949); https://doi.org/10.1039/jr9490002971. (b) H. Chikashita, S. Nishida, M. Miyazaki, Y. Morita and K. Itoh, Bull. Chem. Soc. (Japan), 60, 737 (1987); https://doi.org/10.1246/bcsj.60.737. (c) S. Kumar, V. Kansal and A. Bhaduri, Indian J. Chem., 20B, 254 (1991); (d) F. Pätzold, F. Zeuner, T. Heyer and H.-J. Nielas, Synth. Commun., 22, 281 (1992); https://doi.org/10.1080/00397919208021304. (e) R.L. Lombardy, F.A. Tanious, K. Ramachandran, R.R. Tidwell and W.D. Wilson, J. Med. Chem., 39, 1452 (1996); https://doi.org/10.1021/jm9507946. (f) P.L. Beaulieu, B. Hache and E. von Moos, Synthesis, 1683 (2003); https://doi.org/10.1055/s-2003-40888.
(a) Z.-H. Zhang, L. Yin and Y.-M. Wang, Catal. Commun., 8, 1126 (2007); https://doi.org/10.1016/j.catcom.2006.10.022. (b) Z.H. Zhang, L. Yin, Y. Li and Y.M. Wang, Tetrahedron Lett., 46, 889 (2005); https://doi.org/10.1016/j.tetlet.2004.11.161.
(a) C. Chen and Y.J. Chen, Tetrahedron Lett., 45, 113 (2004); https://doi.org/10.1016/j.tetlet.2003.10.095. (b) J.P. Mayer, G.S. Lewis, C. McGee and D. Bankaitis-Davis, Tetrahedron Lett., 39, 6655 (1998); https://doi.org/10.1016/S0040-4039(98)01427-0.
V. Sareen, U. Gupta, V. Khatri and S. Chug, Indian J. Heterocycl. Chem., 17, 355 (2008).
S.A. Siddiqui, U.C. Narkhede, S.S. Palimbar, T. Danial, R.J. Lahoti and K.V. Srinivasan, Tetrahedron, 61, 3539 (2005); https://doi.org/10.1016/j.tet.2005.01.116.
F.E. Hahn and M.C. Jahnke, Angew. Chem., 120, 3166 (2008); https://doi.org/10.1002/ange.200703883.
M. Suzuki, S. Maeda and K. Matsumoto, Boll. Chim. Farm., 34, 3111 (1986).
L. Almirante, A. Mugnaini, P. Rugarli, A. Gamba, E. Zefelippo, N.D. Toma and W. Murmann, J. Med. Chem., 12, 122 (1969); https://doi.org/10.1021/jm00301a031.
F. Suzuki, T. Kuroda, T. Tamura, S. Sato, K. Ohmori and S. Ichikawa, J. Med. Chem., 35, 2863 (1992); https://doi.org/10.1021/jm00093a020.