Main Article Content
Abstract
A simple and efficient protocol for the synthesis of Schiff bases via condensation reaction of electron rich heterocyclic amines with electrophilic carbon of the carbonyl compound. Recently an impressive and important area in catalysis involved organic synthesis is the best implementation of Lewis acids as a acid catalyst for Schiff base synthesis. The higher acidic property and proper loading of catalyst leads to proper participation in reaction as a catalyst. The reactions of these Lewis acids are enhanced by porous solid support as heterogeneous catalyst. We report herein an efficient concise green synthesis of a new kind of β-lactam derivatives of 2-amino-6-nitro-benzothiazole via SiO2/P2O5 Lewis acid catalyzed Schiff bases. The reaction was carried out by the preparation of Schiff base through the condensation reaction of various aromatic aldehydes with substituted aromatic amines in the presence of P2O5/SiO2 under green conditions by simple conventional methods. Further this Schiff base used for the green synthesis of β-lactams by the reaction with chloro-acetyl chloride. The advantage of this reaction is good dispersion of active reagent sites, associated selectivity and easier work up with reusable catalyst. These qualities combined together prove these processes as truly eco-friendly green protocol with high product yields and short reaction time.
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Copyright (c) 2020 Asian Journal of Organic & Medicinal Chemistry
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References
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- A. Hasaninejad, A. Zare, H. Sharghi and M. Shekouhy, P2O5/SiO2 An Efficient, Green and Heterogeneous Catalytic System for the Solvent-Free Synthesis of N-sulfonyl Imines, ARKIVOC, 64 (2008); https://doi.org/10.3998/ark.5550190.0009.b06
- T. Khan and R. Yadav, Silica-Supported P2O5 as an Efficient Heterogen-eous Catalyst for the One Pot Synthesis of 3-Amino-imidazo[2,1-b]-(1,3)benzothiazole under Green Conditions, J. Heterocycl. Chem., 56, 11 (2019); https://doi.org/10.1002/jhet.3334
- N. Mishra, S.S. Gound, R. Mondal and R. Yadav, Synthesis, Character-ization and Antimicrobial Activities of Benzothiazole-imino-benzoic Acid Ligands and their Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) Complexes, Results in Chemistry, 1, 100006 (2019); https://doi.org/10.1016/j.rechem.2019.100006
- H. Naeimi, F. Salimi and K. Rabie, Mild and Convenient One Pot Synthesis of Schiff Bases in the Presence of P2O5/Al2O3 as New Catalyst under Solvent-Free Conditions, J. Mol. Catal. Chem., 260, 100 (2006); https://doi.org/10.1016/j.molcata.2006.06.055
- K. Avasthi, R. Yadav and T. Khan, Greener and Efficient Synthesis of Some Novel Substituted Azitidinones with 4-Aminopyridine via Heterogenous Catalyst, J. Appl. Chem., 3, 1899 (2014).
References
N.E.A. Abdel Sattar, A.M. El-Naggar and M.S.A. Abdel-Mottaleb, Novel Thiazole Derivatives of Medicinal Potential: Synthesis and Modeling, J. Chem., 2017, 4102796 (2017); https://doi.org/10.1155/2017/4102796
H. Ceric, M. Šindler-Kulyk, M. Kovaèevic, M. Peric and A. Živkovic, Azetidinone-Isothiazolidinones: Stereoselective Synthesis and Antibacterial Evaluation of New monocyclic Beta-Lactams, Bioorg. Med. Chem., 18, 3053 (2010); https://doi.org/10.1016/j.bmc.2010.03.045
H. Tokuyama, K. Okuyama, Y. Momoi, K. Sugimoto and K. Okano, Synthetic Studies toward Haouamine B: Construction of Indenotetra-hydropyridone Skeleton, Synlett, 73 (2011); https://doi.org/10.1055/s-0030-1259096
M. Hodge, O.-H. Chen, S. Bane, S. Sharma, M. Loew, A. Banerjee, A.A. Alcaraz, J.P. Snyder and D.G.I. Kingston, Synthesis and Bioactivity of a Side Chain Bridged Paclitaxel: A Test of the T-Taxol Conformation, Bioorg. Med. Chem. Lett., 19, 2884 (2009); https://doi.org/10.1016/j.bmcl.2009.03.063
B. Alcaide, P. Almendros and C. Aragoncillo, b-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-b-Lactam Products, Chem. Rev., 107, 4437 (2007); https://doi.org/10.1021/cr0307300
B.K. Banik and F.F. Becker, Unprecedented Stereoselectivity in the Staudinger Reaction with Polycyclic Aromatic Imines, Tetrahedron Lett., 41, 6551 (2000); https://doi.org/10.1016/S0040-4039(00)01126-6
J. Marco-Contelles, b-Lactam Synthesis by the Kinugasa Reaction, Angew. Chem., 43, 2198 (2004); https://doi.org/10.1002/anie.200301730
T. Khan, R. Yadav and S.S. Gound, An Efficient Synthesis and Anti-bacterial Activity of Some Novel 2-Azetidinone Derivatives of 4H-1,2,4-Triazoles under Mild Conditions, J. Heterocycl. Chem., 55, 1042 (2018); https://doi.org/10.1002/jhet.3136
H. Eshghi and A. Hassankhani, Phosphorus Pentoxide Supported on Silica Gel and Alumina (P2O5/SiO2, P2O5/Al2O3) as Useful Catalysts in Organic Synthesis, J. Iran. Chem. Soc., 9, 467 (2012); https://doi.org/10.1007/s13738-011-0057-0
A. Hasaninejad, A. Zare, H. Sharghi and M. Shekouhy, P2O5/SiO2 An Efficient, Green and Heterogeneous Catalytic System for the Solvent-Free Synthesis of N-sulfonyl Imines, ARKIVOC, 64 (2008); https://doi.org/10.3998/ark.5550190.0009.b06
T. Khan and R. Yadav, Silica-Supported P2O5 as an Efficient Heterogen-eous Catalyst for the One Pot Synthesis of 3-Amino-imidazo[2,1-b]-(1,3)benzothiazole under Green Conditions, J. Heterocycl. Chem., 56, 11 (2019); https://doi.org/10.1002/jhet.3334
N. Mishra, S.S. Gound, R. Mondal and R. Yadav, Synthesis, Character-ization and Antimicrobial Activities of Benzothiazole-imino-benzoic Acid Ligands and their Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) Complexes, Results in Chemistry, 1, 100006 (2019); https://doi.org/10.1016/j.rechem.2019.100006
H. Naeimi, F. Salimi and K. Rabie, Mild and Convenient One Pot Synthesis of Schiff Bases in the Presence of P2O5/Al2O3 as New Catalyst under Solvent-Free Conditions, J. Mol. Catal. Chem., 260, 100 (2006); https://doi.org/10.1016/j.molcata.2006.06.055
K. Avasthi, R. Yadav and T. Khan, Greener and Efficient Synthesis of Some Novel Substituted Azitidinones with 4-Aminopyridine via Heterogenous Catalyst, J. Appl. Chem., 3, 1899 (2014).