Chemistry Journal
Articles Information
Chemistry Journal, Vol.1, No.1, Feb. 2015, Pub. Date: Feb. 2, 2015
Mg-Al Hydrotralcite Catalyzed Efficient One-Pot Synthesis of 4-H-Benzo[b]Pyrans, 2-Aryl Benzimidazole and 2-Aryl-4,5-Dihydro-1H-Imidazole Derivatives
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Authors
[01] Rohit Gupta, Department of Chemical Sciences, Indian Institute of Science Education and Research-Kolkata (IISER-K), Mohanpur, Nadia,West Bengal, India.
[02] Savita Ladage, Department of Chemistry, Homi Bhabha Centre for Science Education, Tata Institute of Fundamental Research, Mumbai, Maharashtra, India.
[03] Lakshmy Ravishankar, Department of Chemistry, KET’s V.G. Vaze College of Arts, Science & Commerce, Mulund (East), Mumbai, Maharashtra, India.
Abstract
An environment friendly synthesis of 2-amino-3-cyano-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetra¬hydrobenzo[b]pyran, 2- aryl benzimidazole and 2-aryl-4,5-dihydro-1H-imidazole derivatives using Mg-Al hydrotalcite as an efficient catalyst has been developed. The excellent efficiency of the catalyst can be attributed to its Lewis acidic sites which resulted in higher reaction yields for different substituted benzaldehydes and shorter reaction time compared to conventional synthetic procedures. An added advantage is reusability of the catalyst, which demonstrates consistent activity over significant number of cyclesafter filtration and washing with ethanol.
Keywords
Multicomponent Reactions, Green Reactions, Mg-Al Hydrotalcite, Pyrans, Benzimidazole, Imidazole, Lewis Acid
References
[01] (a) Ugi, I. Pure Appl. Chem. 2001, 731, 87. (b) Dömling, A.; Ugi, I. Angew. Chem. Int. 2000, 39, 3168.
[02] (a) Varma, R. S.J. Heterocycl. Chem. 1999, 36, 1565. (b) Eicher, T.; Hauptmann The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications 2nd Ed. 2003, Wiley - VCH, Weinheim.
[03] Preston, P. N. Chem. Rev. 1974, 74, 279.
[04] Horton, D. A.; Bourne, G. T.; Sinythe, M. L. Chem. Rev.2003, 103,893.
[05] Alamgir, M.; Black, St. C. D.; Kumar, N. T. Heterocycl. Chem. 2007, 9, 87.
[06] (a) Jones, R. C. F.; Nichols, J. R. Tetrahedron Lett. 1990, 31, 1771. (b) Jones, C.; Smallridge, M. J.; Chapleo, C. B. J. Chem. Soc. Perkin Trans. 1991,385. (c) Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y.Tetrahedron Lett.1996, 37, 4969. (d) Lin, Y. R.; Zhou, X. T.; David, L. X.; Sun, J. J. Org. Chem.1997,62, 1799. (e) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997,62,3586. (f) Jung, M. E.; Huang, A. Org. Lett.2000, 2, 2659.
[07] (a) Jonesv, R. C. F.; Turner, I.;Howard, K. J.;Tetrahedron Lett. 1993,34,6329. (b) Langlois, Y.;Dalko, P. I.J. Org. Chem.1998, 63, 8107. (c) Jones, R. C. F.;Howard,S.; Naith, K. J.Tetrahedron Lett. 1996,37, 1707.
[08] (a) Corey, E. J.;Grogan, M. J.Org. Lett.1999, 1,157. (b) Isober, T.; Fukuda,K.; Araki, Y.;Ishikawa, T.Chem. Commun. 2001,243.
[09] (a) Botteghi, C.;Schionato, A.;Chelucci, G.; Brunner, H.;Kurzinger, A.;Obermann,U. J.Organomet. Chem.1989, 370, 17. (b) Morimoto, T.; Tachibana, K.;Achiwa, K.Synlett,2003, 783.(c) Davinport, A. J.; Davies, D. L.;Faweett, J.;Russell, D. R.J.Chem. Soc., Perkin Trans 2001,11,500. (d) Menges, F.;Neuburger, M.;Pfaltz,A.Org. Lett. 2002, 44,713. (e) Boland,N. A.; Casey, M.; Hynes, S. J.;Matthews,J. W.;Muller-Bunz, H.;Wilkes, P. Org. Biomol. Chem.2004, 2, 1995.
[10] (a) Preston, P. N.; Stevens, M F. G.;Tennant, G.Benzimidazoles and Congeneric Tricyclic Compounds, Part 2, John Wiley & Sons: New York 1980. (b) Cedillo-Rivera, R.;Munoz, O.J. Med. Microbiol1992, 37, 221 (c) Chavez, B.;Cedillo-Rivera, R.;Martiner-Palomo, A.J. Protozool1992,39, 510. (d) Navarrete-Vazquez, G.;Cedillo, R.; Hernandez-Campos, A.;Yepez, L; Hernandez-Luis, F.; Valdez, J.; Morales, R.;Cortes, R.; Hernandez, M.;Castillo, R.Bioorg. Med. Chem. Lett.2001,11, 187.
[11] Mobinikhaledi, A.; Fard, M.A.B.ActaChim. Slov.2010,57,931.
[12] Ellis, G. P.In The Chemistry of Heterocyclic Compounds. Chromenes, Chromanes and Chromones;Weissberger, A., Taylor, E. C., Eds.; John Wiley: New York, 1977, chapter 11, pp 11.
[13] Armetso, D.;Horspool, W. M.; Martin, N.; Ramos, A.J. Org. Chem.1989, 54, 3069.
[14] Kshirsagar, S. W.;Patil, N. R.;Samant, S. D.Green Chem. Lett. and Rev.2010, 3, 335.
[15] Suzuki, E.; Ono,Y.Bull. Chem. Soc. Jpn.1988,61, 1008.
[16] Suzuki, E.; Okamoto, M.; Ono, Y.J. Mol. Catal. 1990,61, 283.
[17] Cativiela, C.;Figueras, F.; Garcia, J. I.; Mayoral, J. A.;Zurbano, M. M.Synth. Commun.1995,25, 1745.
[18] Cativiela, C.; Figueras, F.;Fraile,J.M.; Garcia, J. I., Mayoral, J. A.Tetrahedron Lett.1995, 36, 4125.
[19] Shen, J.; Kobe, J. M.; Chen, Y.; Dumesic, J. A.Langmuir 1994,10, 3902.
[20] Cavani, F.;Trifiro, F.;Vaccari, A.Catal. Today 1991, 11, 173.
[21] Sharghi, H.;Beyzavi, M. H.;Doroodmand, M. M.Eur. J. Org.Chem. 2008,24,4126.
[22] Du, L. H.; Wang, Y. G.Synthesis2007,675.
[23] Chakrabarty, M.; Mukherjee, R.;Karmakar, S.;Harigaya, Y. Monatsh Chem.2007, 138, 1279.
[24] Heravi, M.M.;Tajbakhsh, M.;Ahmadi,A. N.;Mohajerani, B.Monatsh Chem. 2006,137, 175.
[25] Sahu, D. P.; Ponnala, S.Synth. Commun. 2006, 36, 2189.
[26] Allouma,A. B.;Bougrin, K.;Soufiaoui,M.Tetrahedron Lett.2003, 44,5935.
[27] Han, X.; Ma, H.; Wang, Y. Russ.J. Org. Chem.2008, 44, 863.
[28] Haneda, S.;Okui, A.;Ueba, C.; Hayashi, M.Tetrahedron2007, 63, 2414.
[29] Wang, X. S.; Shi, D. Q.;Tu, S. J.; Yao, C. S. Synth. Commun.2003, 33, 119.
[30] Jin, T.S.; Wang, A. Q.; Wang, X.; Zhang, J. S.; Li, T.S.Synlett2004, 871.
[31] Gurumurthi, S; Sundari, V.; Vallippan, R.E-J Chem.2009, 6(S1), S466.
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