- About this Journal ·
- Abstracting and Indexing ·
- Aims and Scope ·
- Article Processing Charges ·
- Author Guidelines ·
- Bibliographic Information ·
- Citations to this Journal ·
- Contact Information ·
- Editorial Board ·
- Editorial Workflow ·
- Free eTOC Alerts ·
- Publication Ethics ·
- Recently Accepted Articles ·
- Reviewers Acknowledgment ·
- Submit a Manuscript ·
- Subscription Information ·
- Table of Contents
Organic Chemistry International
Volume 2012 (2012), Article ID 153159, 5 pages
CES as an Efficient Natural Catalyst for Synthesis of Schiff Bases under Solvent-Free Conditions: An Innovative Green Approach
Organic Research Laboratory, Department of Chemistry, Padmabhushan Dr. Vasantraodada Patil College, Sangli District, Tasgaon 416312, India
Received 3 September 2012; Revised 16 November 2012; Accepted 18 November 2012
Academic Editor: William Setzer
Copyright © 2012 Suresh Patil et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- 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, pp. 2159–2169, 2001.
- 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, no. 16, pp. 3443–3453, 2007.
- J. O. Metzger, “Solvent-free organic syntheses,” Angewandte Chemie—International Edition, vol. 37, no. 21, pp. 2975–2978, 1998.
- C. J. Li and T. H. Chan, “Organic syntheses using indium-mediated and catalyzed reactions in aqueous media,” Tetrahedron, vol. 55, no. 37, pp. 11149–11176, 1999.
- T. P. Loh, J. M. Huang, S. H. Goh, and J. J. Vittal, “Aldol reaction under solvent-free conditions: highly stereoselective synthesis of 1,3-amino alcohols,” Organic Letters, vol. 2, no. 9, pp. 1291–1294, 2000.
- R. S. Varma and V. V. Namboodiri, “Solvent-free preparation of ionic liquids using a household microwave oven,” Pure and Applied Chemistry, vol. 73, no. 8, pp. 1309–1313, 2001.
- K. Tanaka and F. Toda, “Solvent-free organic synthesis,” Chemical Reviews, vol. 100, no. 3, pp. 1025–1074, 2000.
- C. Unaleroglu, B. Temelli, and T. Hokelek, “Conformational and structural analysis of N-N′-bis(4-methoxybenzylidene)ethylenediamine,” Journal of Molecular Structure, vol. 570, no. 1–3, pp. 91–95, 2001.
- C. H. Li and T. C. Chang, “Studies on thermotropic liquid crystalline polymers-Part II. Synthesis and properties of poly(azomethine-ether),” European Polymer Journal, vol. 27, no. 1, pp. 35–39, 1991.
- P. J. Blower, “Small coordination complexes as radiopharmaceuticals for cancer targeting,” Transition Metal Chemistry, vol. 23, no. 1, pp. 109–112, 1997.
- G. Wilkinson, Comprehensive Coordination Chemistry, Pergamon Press, New York, NY, USA, 1987.
- P. H. Wang, J. G. Keck, E. J. Lien, and M. M. C. Lai, “Design, synthesis, testing, and quantitative structure-activity relationship analysis of substituted salicylaldehyde Schiff bases of 1-amino-3-hydroxyguanidine tosylate as new antiviral agents against coronavirus,” Journal of Medicinal Chemistry, vol. 33, no. 2, pp. 608–614, 1990.
- A. W. Tai, E. J. Lien, M. M. C. Lai, and T. A. Khwaja, “Novel N-hydroxyguanidine derivatives as anticancer and antiviral agents,” Journal of Medicinal Chemistry, vol. 27, no. 2, pp. 236–238, 1984.
- N. Alizadeh, S. Ershad, H. Naeimi, H. Sharghi, and M. Shamsipur, “Synthesis of a new naphthol-derivative salen and spectrophotometric study of the thermodynamics and kinetics of its complexation with copper(II) ion in binary dimethylsulfoxide-acetonitrile mixtures,” Polish Journal of Chemistry, vol. 73, no. 6, pp. 915–925, 1999.
- D. Sanz, A. Perona, R. M. Claramunt, and J. Elguero, “Synthesis and spectroscopic properties of Schiff bases derived from 3-hydroxy-4-pyridinecarboxaldehyde,” Tetrahedron, vol. 61, no. 1, pp. 145–154, 2005.
- J. M. Fernández-G, F. Del Rio-Portilla, B. Quiroz-García, R. A. Toscano, and R. Salcedo, “The structures of some ortho-hydroxy Schiff base ligands,” Journal of Molecular Structure, vol. 561, no. 1–3, pp. 197–207, 2001.
- J. A. Sclatani, M. T. Maranto, T. M. Sisk, and S. A. V. Arman, “Terminal alkylation of linear polyamines,” Journal of Organic Chemistry, vol. 61, no. 9, pp. 3221–3222, 1996.
- R. Ando, T. Yagyu, and M. Maeda, “Characterization of oxovanadium (IV)-Schiff-base complexes and those bound on resin, and their use in sulfide oxidation,” Inorganica Chimica Acta, vol. 357, no. 8, pp. 2237–2244, 2004.
- H. Sharghi and K. Niknam, “Conversion of alcohols into amides using alumina-methanesulfonic acid (AMA) in nitrile solvents,” Iranian Journal of Chemistry and Chemical Engineering, vol. 18, no. 1, pp. 36–39, 1999.
- K. Ambroziak, R. Pelech, E. Milchert, T. Dziembowska, and Z. Rozwadowski, “New dioxomolybdenum(VI) complexes of tetradentate Schiff base as catalysts for epoxidation of olefins,” Journal of Molecular Catalysis A, vol. 211, no. 1-2, pp. 9–16, 2004.
- H. Suga, T. Fudo, and T. Ibata, “Cu(I)-binaphthyldiimine catalyzed asymmetric cyclopropanation of olefin with diazoacetate,” Synlett, no. 8, pp. 933–935, 1998.
- Z. H. Yang, L. X. Wang, Z. H. Zhou, Q. L. Zhou, and C. C. Tang, “Synthesis of new chiral Schiff bases and their application in the asymmetric trimethylsilylcyanation of aromatic aldehydes,” Tetrahedron Asymmetry, vol. 12, no. 11, pp. 1579–1582, 2001.
- G. J. Kim and J. H. Shin, “Application of new unsymmetrical chiral Mn(III), Co(II,III) and Ti(IV) salen complexes in enantioselective catalytic reactions,” Catalysis Letters, vol. 63, no. 1-2, pp. 83–90, 1999.
- C. Sasaki, K. Nakajima, and M. Kojima, “Preparation and characterization of optically active quadridentate Schiff base-titanium (IV) complexes and the catalytic properties of these complexes on asymmetric oxidation of methyl phenyl sulfide with organic hydro peroxides,” Bulletin of the Chemical Society Japan, vol. 64, no. 4, pp. 1318–1324, 1991.
- W. Adam, R. T. Fell, V. R. Stegmann, and C. R. Saha-Möller, “Synthesis of optically active α-hydroxy carbonyl compounds by the catalytic, enantioselective oxidation if silyl enol ethers and ketene acetals with (salen)manganese(III) complexes,” Journal of the American Chemical Society, vol. 120, no. 4, pp. 708–714, 1998.
- T. M. Ovitt and G. W. Coates, “Stereoselective ring-opening polymerization of meso-lactide: synthesis of syndiotactic poly(lactic acid),” Journal of the American Chemical Society, vol. 121, no. 16, pp. 4072–4073, 1999.
- M. Shamsipur, S. Sadeghi, H. Naeimi, and H. Sharghi, “Iodide ion-selective PVC membrane electrode based on a recently synthesized salen-Mn(II) complex,” Polish Journal of Chemistry, vol. 74, no. 2, pp. 231–238, 2000.
- N. Alizadeh, S. Ershad, H. Naeimi, H. Sharghi, and M. Shamsipur, “Copper(II)-selective membrane electrode based on a recently synthesized naphthol-derivative Schiff's base,” Fresenius' Journal of Analytical Chemistry, vol. 365, no. 6, pp. 511–515, 1999.
- M. M. Ardakany, A. A. Ensafi, H. Naeimi, A. Dastanpour, and A. Shamlli, “Highly selective lead(II) coated-wire electrode based on a new Schiff base,” Sensors and Actuators B, vol. 96, no. 1-2, pp. 441–445, 2003.
- A. R. Khorrami, H. Naeimi, and A. R. Fakhari, “Determination of nickel in natural waters by FAAS after sorption on octadecyl silica membrane disks modified with a recently synthesized Schiff's base,” Talanta, vol. 64, no. 1, pp. 13–17, 2004.
- M. Shamsipur, M. Yousefi, M. Hosseini, M. R. Ganjali, H. Sharghi, and H. Naeimi, “A Schiff base complex of Zn(II) as a neutral carrier for highly selective PVC membrane sensors for the sulfate ion,” Analytical Chemistry, vol. 73, no. 13, pp. 2869–2874, 2001.
- A. R. Fakhari, A. R. Khorrami, and H. Naeimi, “Synthesis and analytical application of a novel tetradentate N2O2 Schiff base as a chromogenic reagent for determination of nickel in some natural food samples,” Talanta, vol. 66, no. 4, pp. 813–817, 2005.
- M. Shamsipur, A. R. Ghiasvand, H. Sharghi, and H. Naeimi, “Solid phase extraction of ultra trace copper(II) using octadecyl silica membrane disks modified by a naphthol-derivative Schiff's base,” Analytica Chimica Acta, vol. 408, no. 1-2, pp. 271–277, 2000.
- Y. Gao and C. Xu, “Synthesis of dimethyl carbonate over waste eggshell catalyst,” Catalysis Today, vol. 190, no. 1, pp. 107–111, 2012.
- H. Schiff, “Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen,” Justus Liebigs Annalen der Chemie, vol. 131, no. 1, pp. 118–119, 1864.
- R. B. Moffett and N. Rabjohn, Organic Synthesis, vol. 4, John Wiley & Sons, New York, NY, USA, 1963.
- F. H. Westheimer and K. Taguchi, “Catalysis by molecular sieves in the preparation of ketimines and enamines,” Journal of Organic Chemistry, vol. 36, no. 11, pp. 1570–1572, 1971.
- B. E. Love and J. Ren, “Synthesis of sterically hindered imines,” Journal of Organic Chemistry, vol. 58, no. 20, pp. 5556–5557, 1993.
- A. Vass, J. Dudás, and R. S. Varma, “Solvent-free synthesis of N-sulfonylimines using microwave irradiation,” Tetrahedron Letters, vol. 40, no. 27, pp. 4951–4954, 1999.
- 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 Communications, vol. 42, no. 8, pp. 1177–1183, 2012.
- 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, pp. 203–208, 2011.
- H. Naeimi and K. Rabiei, “Montmorillonite as a heterogeneous catalyst in the efficient, mild and one pot synthesis of Schiff bases under solvent-free conditions,” Journal of the Chinese Chemical Society, vol. 59, no. 2, pp. 208–212, 2012.
- L. Ravishankar, S. A. Patwe, N. Gosarani, and A. Roy, “Cerium(III)-catalyzed synthesis of schiff bases: a green approach,” Synthetic Communications, vol. 40, no. 21, pp. 3177–3180, 2010.
- H. Naeimi, F. Salimi, and K. Rabiei, “Mild and convenient one pot synthesis of Schiff bases in the presence of P2O5/Al2O3 as new catalyst under solvent-free conditions,” Journal of Molecular Catalysis A, vol. 260, no. 1-2, pp. 100–104, 2006.
- A. K. Chakraborti, S. Bhagat, and S. Rudrawar, “Magnesium perchlorate as an efficient catalyst for the synthesis of imines and phenylhydrazones,” Tetrahedron Letters, vol. 45, no. 41, pp. 7641–7644, 2004.
- G. C. Look, “Trimethylorthoformate: a mild and effective dehydrating reagentfor solution and solid phase imine formation,” Tetrahedron Letters, vol. 36, no. 17, pp. 2937–2940, 1995.
- F. T. Boullet, “A simple, convenient and mild of imines on alumina surface without solvent,” SynthesisSynthesis, no. 6-7, pp. 679–681, 1985.
- A. Y. Vibhute, S. S. Mokle, Y. S. Nalwar, Y. B. Vibhute, and V. M. Gurav, “An efficient and operationally simple synthesis of some new Schiff bases using grinding technique,” Bulletin of the Catalysis Society of India, vol. 8, pp. 164–168, 2009.
- 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, pp. 22–33, 2009.
- R. S. Varma, R. Dahiya, and S. Kumar, “Clay catalyzed synthesis of imines and enamines under solvent-free conditions using microwave irradiation,” Tetrahedron Letters, vol. 38, no. 12, pp. 2039–2042, 1997.