Natural Acid Catalyzed Synthesis of Schiff under Solvent-Free Condition: As a Green Approach

DOI: 10.4236/ijoc.2012.22025   PDF   HTML     5,246 Downloads   10,544 Views   Citations


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S. Patil, S. Jadhav, M. Deshmukh and U. Patil, "Natural Acid Catalyzed Synthesis of Schiff under Solvent-Free Condition: As a Green Approach," International Journal of Organic Chemistry, Vol. 2 No. 2, 2012, pp. 166-171. doi: 10.4236/ijoc.2012.22025.

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[1] J. O. Metzger, “Solvent-Free Organic Syntheses,” Ange-wandte Chemie International Edition, Vol. 37, No. 21, 1998, pp. 2975-2978. doi:10.1002/(SICI)1521-3773(19981116)37:21<2975::AID-ANIE2975>3.0.CO;2-A
[2] C. J. Li and T. H. Chan, “Organic Syntheses Using Indium-Mediated and Catalyzed Reactions in Aqueous Media,” Tetrahedron, Vol. 55, No. 37, 1999, pp. 11149-11176. doi:10.1016/S0040-4020(99)00641-9
[3] G. W. V. Cave, C. L. Raston and J. L. Scott, “Recent Advances in Solventless Organic Reactions: Towards Benign Synthesis with Remarkable Versatility,” Chemical Communications, No. 21, 2001, pp. 2159-2169. doi:10.1039/b106677n
[4] C. Imrie, P. Kleyi, V. O. Nyamori, T. I. A. Gerber, D. C. Levendis and J. Look, “Further Solvent-Free Reactions of Ferrocenylaldehydes: Synthesis of 1,1’-Ferrocenyldiimines and Ferrocenylacrylonitriles,” Journal of Organometallic Chemistry, Vol. 692, 2007, pp. 3443-3453. doi:10.1016/j.jorganchem.2007.04.011
[5] F. D. Popp, “Synthesis of Potential Anticancer Agents. II. Some Schiff Bases,” The Journal of Organic Chemistry, Vol. 26, No. 1, 1961, pp. 1566-1568. doi:10.1021/jo01064a063
[6] D. J. Hadjipavlou-litina and A. A. Geronikaki, “Thiazolyl and Benzothiazolyl Schiff Bases as Novel Lipoxygenase’s Inhibitors and Anti-Inflammatory Agents, Synthesis and Biological Evaluation,” Drug Design and Discovery, Vol. 15, No. 3, 1996, pp. 199-206.
[7] K. N. Venugopala and V. A. Jayashree, “Microwave-Induced Synthesis of Schiff Bases of Aminothiazolyl Bro-mocoumarins as Antibacterials,” Indian Journal of Pharmaceutical Sciences, Vol. 70, 2008, pp. 88-90. doi:10.4103/0250-474X.40338
[8] N. Solak and S. Rollas, “Synthesis and Antituberculosis Activity of 2-(Aryl /alkylamino)-5-(4-aminophenyl)-1,3, 4-thiadiazoles and Their Schiff Bases,” Online Journal of Organic Chemistry, Vol. 12, 2006, pp. 173-181.
[9] S. J. Wadher, M. P. Puranik, N. A. Karande and P. G. Yeole, “Synthesis and Biological Evaluation of Schiff Base of Dapsone and Their derivative as Antimicrobial Agents,” International Journal of PharmTech Research, Vol. 1, No. 1, 2009, pp. 22-33.
[10] A. L. Cates and S. M. Rasheed, “Phosphorus GABA Analogues as Potential Prodrugs,” Pharmaceutical Research, Vol. 1, No. 6, 1984, pp. 271-273. doi:10.1023/A:1016350119870
[11] V. V. Kuznetsov, A. R. Palma, A. E. Aliev, A. V. Varlamov and N. S. Prostakov, “Regioselective Cyclization of 1-Allyl-1-α(β)-naphthylaminocyclohexanes to 4-Methyl- 1,2,3,4-tetrahydrospiro(cyclohexane-1,2-benzo(h(f))quinolin- es),” Zhurnal Organicheskoi Khimii, Vol. l27, 1991, pp. 1579-1581.
[12] A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris and T. Lectka, “The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of b-Lactams,” Journal of American Chemical Society, Vol. 124, 2002, pp. 6626-6635. doi:10.1021/ja0258226
[13] O. Tsuge and R. Kanemasa, “Recent Advances in Azo-methine Ylide Chemistry,” Advances in Heterocyclic Chemistry, Vol. 45, 1989, pp. 231-349. doi:10.1016/S0065-2725(08)60332-3
[14] M. F. Aly, M. I. Younes and S. A. M. Metwally, “Non- Decarboxylative 1,3-Dipolar Cycloadditions of Imines of α-Amino Acids as a Route to Proline Derivatives,” Tet-rahedron, Vol. 50, No. 10, 1994, pp. 3159-3168. doi:10.1016/S0040-4020(01)81114-5
[15] H. Schiff, “Mittheilungen aus dem Universitatslaboratorium in Pisa: Eine neue Reihe Organischer Basen,” Justus Liebigs Annalen der Chemie, Vol. 131, No. 1, 1864, pp. 118-119. doi:10.1002/jlac.18641310113
[16] R. B. Moffett and N. Rabjohn, Eds., “Organic Synthesis,” John Wiley & Sons, Inc., New York, 1963, pp. 605-608.
[17] M. E. Kuehne, “The Applications of Enamines to a New Synthesis of b-Ketonitriles,” Journal of American Chemical Society, Vol. 81, No. 20, 1959, pp. 5400-5404. doi:10.1021/ja01529a037
[18] K. Taguchi and F. H. Westheimer, “Catalysis by Molecular Sieves in the Preparation of Ketimines and Enamines,” The Journal of Organic Chemistry, Vol. 36, No. 11, 1971, pp. 1570-1572. doi:10.1021/jo00810a033
[19] B. E. Love and J. Ren, “Synthesis of Sterically Hindered Imine,” The Journal of Organic Chemistry, Vol. 58, No. 20, 1993, pp. 5556-5559. doi:10.1021/jo00072a051
[20] G. C. Look, M. M. Murphy, D. A. Campbell and M. A. Gallop, “Trimethylorthoformate: A Mild and Effective De-hydrating Reagent for Solution and Solid Phase Imine Formation,” Tetrahedron Letters, Vol. 36, No. 17, 1995, pp. 2937-2940. doi:10.1016/0040-4039(95)00442-F
[21] R. S. Vaas, J. Duda’s and R. S. Varma, “Solvent-Free Synthesis of N-Sulfonylimines Using Microwave Irradiation,” Tetrahedron Letters, Vol. 40, No. 27, 1999, pp. 4951-4954.
[22] J. H. Billman and K. M. J. Tai, “Reduction of Schiff Bases II: Benzhydrylamines and Struc-turally Related Compounds,” The Journal of Organic Chemistry, Vol. 23, No. 4, 1958, pp. 535-539. doi:10.1021/jo01098a009
[23] W. A. White and H. Weingarten, “A Versatile New Enamine Synthesis,” The Journal of Organic Chemistry, Vol. 32, No. 10, 1967, pp. 213-214. doi:10.1021/jo01277a052
[24] F. Texier-Boullet, “A Simple, Convenient, and Mild Synthesis of Imines on Alumina Surface without Solvent,” Synthesis, Vol. 6-7, 1985, pp. 679-681.
[25] H. Naeimi, F. Salimi and K. Rabiei, “Mild and Conven- ient One-Pot Synthesis of Schiff Bases in the Presence of P2O5=Al2O3 as New Catalyst under Solvent-Free Conditions,” Journal of Molecular Catalysis A: Chemical, Vol. 260, No. 1-2, 2006, pp. 100-104. doi:10.1016/j.molcata.2006.06.055
[26] J. Zhu, L. Chen, H. Wu and J. Yang, “Highly Efficient Procedure for the Synthesis of Schiff Bases Using Hydrotalcite-Like Materials as Catalyst,” Clinical Journal of Chemistry, Vol. 27, No. 10, 2009, pp. 1868-1870.
[27] N. Hossein, F. Salimi and K. Rabiei, “Mild and Convenient One Pot Synthesis of Schiff Base in Presence of P2O5/Al2O3 as New Catalyst under Solvent-Free Condition,” Journal of Molecular Catalysis, Vol. 260, No. 1-2, 2006, pp. 100-104. doi:10.1016/j.molcata.2006.06.055
[28] R. S. Varma, R. Dahiya and S. Kumar, “Clay-Catalyzed Synthesis of Imines and Enamines under Solvent-Free Conditions Using Microwave Irradiation,” Tetrahedron Let- ters, Vol. 38, No. 12, 1997, pp. 2039-2042. doi:10.1016/S0040-4039(97)00261-X
[29] M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan and J. Thanusu, “New Environmentally Friendly, Solvent-Free Synthesis of Imines Using Calcium Oxide under Micro-wave Irradiation,” Journal of Chemical Research, Vol. 33, No. 6, 2007, pp. 541-548.
[30] L. Ravishankara, S. A. Patwea, N. Gosarania and A. Roya, “Ce-rium(III)-Catalyzed Synthesis of Schiff Bases: A Green Approach,” Synthetic Communications, Vol. 40, No. 21, 2010, pp. 3177-3180. doi:10.1080/00397910903370725
[31] A. R. Bendale, R. Bhatt, A. Nagar, A. G. Jadhav and G. Vidyasagar, “Schiff Base Synthesis by Unconventional Route: An Innovative Green Approach,” Der Pharma Chemica, Vol. 3, No. 2, 2011, pp. 34-38.
[32] M. B. Deshmukh, S. S. Patil, S. D. Jadhav and P. B. Pawar, “Green Approach for Knoevenagel Condensation of Aromatic Aldehydes with Active Methylene Group,” Synthetic Commutations, in press.
[33] S. Patil, S. D. Jadhav and M. B. Deshmukh, “Natural Acid Catalyzed Multi-Component Reactions as a Green Approach,” Archives of Applied Science Research, Vol. 3, No. 1, 2011, pp. 203-208.
[34] H. Naeimi and K. Rabiei, “Montmorillonite as a Hetero- geneous Catalyst in the Efficient, Mild and One Pot Synthesis of Schiff Bases under Solvent-Free Conditions,” Journal of Chinese Chemical Society, Vol. 58, No. 6, 2011, pp. 1-5.
[35] J. S. Bennette, “Green Synthesis of Aryl Aldimines Using Ethyl Lactate,” US Patent, US 2011/0196174 A1, 2011.
[36] D. Todd, “Schiff Base Puzzle Project,” Journal of Chemical Education, Vol. 69, No. 7, 1992, p. 584. doi:10.1021/ed069p584

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