Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
K2CO3/Al2O3: An Efficient and Recyclable Catalyst for One-Pot, Three Components Synthesis of α-Aminophosphonates and Bioactivity Evaluation
Corresponding Author(s) : N. Bakthavatchala Reddy
Asian Journal of Chemistry,
Vol. 31 No. 10 (2019): Vol 31 Issue 10
Abstract
A simple and efficient method has been employed for synthesis of a novel series of biologically active α-aminophosphonates (4a-j) by reacting 1H-benzo[d]imidazole-2-carbaldehyde (1) and various aromatic amines (2a-j) and diethyl/dimethyl phosphite (3) by Kabachnik-Field's reaction in the presence of efficient heterogeneous K2CO3/Al2O3 catalyst under solvent-free conditions at 140 ºC. Structures of all the compounds were confirmed by 1H, 13C and 31P NMR and LC-MS. In addition to this antioxidant activity were also evaluated.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- J.A. Sikorski, M.J. Miller, D.S. Braccolino, D.G. Cleary, S.D. Corey, J.L. Font, K.J. Gruys, C.Y. Han, K.-C. Lin, P.D. Pansegrau, J.E. Ream, D. Schnur, A. Shah and M.C. Walker, Phosphorus Sulfur Silicon Rel. Elem., 76, 115 (1993); https://doi.org/10.1080/10426509308032372.
- L. Maier and H. Spörri, Phosphorus Sulfur Silicon Rel. Elem., 61, 69 (1991); https://doi.org/10.1080/10426509108027339.
- J. Emsley and D. Hall, In Chemistry of Phosphorus, Harper & Row: London, p. 494 (1976).
- F.R. Atherton, C.H. Hassall and R.W. Lambert, J. Med. Chem., 29, 29 (1986); https://doi.org/10.1021/jm00151a005.
- P. Kafarski and B. Lejczak, Phosphorus Sulfur Silicon Rel. Elem., 63, 193 (1991); https://doi.org/10.1080/10426509108029443.
- C.-W. Guo, S.-H. Wu, F.-L. Chen, Z.-Y. Han, X.-H. Fu and R. Wan, Phosphorus Sulfur Silicon Rel. Elem., 191, 1250 (2016); https://doi.org/10.1080/10426507.2016.1166365.
- H.L. Wang, J. Zhou, Y.G. Qiu, K.S. Feng and R.Y. Chen, Phosphorus Sulfur Silicon Rel. Elem., 104, 135 (1995); https://doi.org/10.1080/10426509508042585.
- J. Zhou, R.Y. Chen and X.F. Yang, Heteroatom Chem., 9, 369 (1998); https://doi.org/10.1002/(SICI)1098-1071(1998)9:4<369::AIDHC4>3.0.CO;2-3.
- A.B. Smith III, C.M. Taylor, S.J. Benkovic and R. Hirschmann, Tetrahedron Lett., 35, 6853 (1994); https://doi.org/10.1016/0040-4039(94)85022-4.
- G.F. Makhaeva, V.V. Malygin, A.Y. Aksinenko, V.B. Sokolov, N.N. Strakhova, A.N. Rasdolsky, R.J. Richardson and I.V. Martynov, Dokl. Biochem. Biophys., 400, 92 (2005); https://doi.org/10.1007/s10628-005-0041-7.
- W. Pan, C. Ansiaux and S.P. Vincent, Tetrahedron Lett., 48, 4353 (2007); https://doi.org/10.1016/j.tetlet.2007.04.113.
- E.K. Baylis, C.D. Campbell and J.G. Dingwall, J. Chem. Soc. Perkin Trans. I, 2845 (1984); https://doi.org/10.1039/p19840002845.
- M.C. Allen, W. Fuhrer, B. Tuck, R. Wade and J.M. Wood, J. Med. Chem., 32, 1652 (1989); https://doi.org/10.1021/jm00127a041.
- B.V.S. Reddy, A.S. Krishna, A.V. Ganesh and G.G.K.S.N. Kumar, Tetrahedron Lett., 52, 1359 (2011); https://doi.org/10.1016/j.tetlet.2011.01.074.
- J. Tang, L. Wang, W. Wang, L. Zhang, S. Wu and D. Mao, J. Fluor. Chem., 132, 102 (2011); https://doi.org/10.1016/j.jfluchem.2010.12.002.
- Z. Karimi-Jaberi, H. Zare, M. Amiri and N. Sadeghi, Chin. Chem. Lett., 22, 559 (2011); https://doi.org/10.1016/j.cclet.2010.11.034.
- H. Firouzabadi, N. Iranpoor and S. Sobhani, Synthesis, 2692 (2004); https://doi.org/10.1055/s-2004-831251.
- S. Bhagat and A.K. Chakraborti, J. Org. Chem., 72, 1263 (2007); https://doi.org/10.1021/jo062140i.
- Ambica, S. Kumar, S.C. Taneja, M.S. Hundal and K.K. Kapoor, Tetrahedron Lett., 49, 2208 (2008); https://doi.org/10.1016/j.tetlet.2008.02.047.
- A.S. Paraskar and A. Sudalai, ARKIVOC, 183 (2006); https://doi.org/10.3998/ark.5550190.0007.a21.
- Z.P. Zhan and J.P. Li, Synth. Commun., 35, 2501 (2005); https://doi.org/10.1080/00397910500212692.
- R. Ghosh, S. Maiti, A. Chakraborty and D. Maiti, J. Mol. Catal. Chem., 210, 53 (2004); https://doi.org/10.1016/j.molcata.2003.09.020.
- P.P. Sun, Z.X. Hu and Z.H. Huang, Synth. Commun., 34, 4293 (2004); https://doi.org/10.1081/SCC-200039361.
- S.A. Sadaphal, S.S. Sonar, A.H. Kategaonkar and M.S. Shingare, Bull. Korean Chem. Soc., 30, 1054 (2009); https://doi.org/10.5012/bkcs.2009.30.5.1054.
- J.S. Yadav, B.V.S. Reddy and P. Sreedhar, Green Chem., 4, 436 (2002); https://doi.org/10.1039/B203934F.
- S. Lee, J.K. Lee, C.E. Song and D.C. Kim, Bull. Korean Chem. Soc., 23, 667 (2002); https://doi.org/10.5012/bkcs.2002.23.5.667.
- S. Lee, J.H. Park, J.K. Lee and J. Kang, Chem. Commun., 1698 (2001); https://doi.org/10.1039/b104967b.
- S. Chandrasekhar, C. Narsihmulu, S.S. Sultana, B. Saritha and S.J. Prakash, Synlett, 505 (2003); https://doi.org/10.1055/s-2003-37508.
- J.H. Clark and C.N. Rhodes, Clean Synthesis using Porous Inorganic Solid Catalysts and Supported Reagents, Royal Society of Chemistry: Cambridge (2000).
- V.S. Gerard and F. Notheisz, Heterogeneous Catalysis in Organic Chemistry, Elsevier: San Diego (2000).
- E. Rafiee, S. Rashidzadeh and A. Azad, J. Mol. Catal. Chem., 261, 49 (2007); https://doi.org/10.1016/j.molcata.2006.07.058.
- A. Davoodnia, M. Bakavoli, G. Barakouhi and N. Tavakoli Hoseini, Chin. Chem. Lett., 18, 1483 (2007); https://doi.org/10.1016/j.cclet.2007.10.013.
- N. Tavakoli-Hoseini and A. Davoodnia, Asian J. Chem., 22, 7197 (2010).
- A. Davoodnia, A. Tavakoli-Nishaburi and T.-H. Niloofar, Bull. Korean Chem. Soc., 32, 635 (2011); https://doi.org/10.5012/bkcs.2011.32.2.635.
- A. Corma and H. Garcia, Adv. Synth. Catal., 348, 1391 (2006); https://doi.org/10.1002/adsc.200606192.
- K. Niknam, B. Karami and M.A. Zolfigol, Catal. Commun., 8, 1427 (2007); https://doi.org/10.1016/j.catcom.2006.12.011.
- K. Niknam, M.A. Zolfigol, A. Khorramabadi-Zad, R. Zare and M. Shayegh, Catal. Commun., 7, 494 (2006); https://doi.org/10.1016/j.catcom.2006.01.004.
- I.V. Kozhevinkov, Catalysis by Poly Oxometalates; Wiley: Chichester, pp 2-22 (2002).
- A.R. Hajipour and A.E. Ruoho, Tetrahedron Lett., 46, 8307 (2005); https://doi.org/10.1016/j.tetlet.2005.09.178.
- S. Kantevari, R. Bantu and L. Nagarapu, J. Mol. Catal. Chem., 269, 53 (2007); https://doi.org/10.1016/j.molcata.2006.12.039.
- A. Davoodnia, M. Roshani, S.H. Malaeke and M. Bakavoli, Chin. Chem. Lett., 19, 525 (2008); https://doi.org/10.1016/j.cclet.2008.01.037.
- A.T. Khan, S. Ghosh and L.H. Choudhury, Eur. J. Org. Chem., 9, 2226 (2006); https://doi.org/10.1002/ejoc.200600006.
- M.Z. Dastmalbaf, A. Davoodnia, M.M. Heravi, N. Tavakoli Hoseini, A. Khojastehnezhad and H.A. Zamani, Bull. Korean Chem. Soc., 32, 656 (2011); https://doi.org/10.5012/bkcs.2011.32.2.656.
- A. Khojastehnezhad, A. Davoodnia, M. Bakavoli, N. Tavakoli-Hoseini and M. Zeinali-Dastmalbaf, Chin. J. Chem., 29, 297 (2011); https://doi.org/10.1002/cjoc.201190081.
- H. Li, X. Yu, S.-T. Tu, J. Yan and Z. Wang, J. Appl. Catal. A, 387, 215 (2010); https://doi.org/10.1016/j.apcata.2010.08.030.
- A. Emrani, A. Davoodnia and N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 32, 2385 (2011); https://doi.org/10.5012/bkcs.2011.32.7.2385.
- G. Sravya, G.V. Zyryanov, A. Balakrishna, K.M. Kumar Reddy, C.S. Reddy, G.M. Reddy, A. Camilo Jr., J.R. Garcia and N.B. Reddy, Phosphorus, Sulfur Silicon Rel. Elem., 193, 562 (2018); https://doi.org/10.1080/10426507.2018.1455201.
- M. Burits and F. Bucar, Phytother. Res., 14, 323 (2000); https://doi.org/10.1002/1099-1573(200008)14:5<323::AIDPTR621>3.0.CO;2-Q.
- M. Cuendet, K. Hostettmann, O. Potterat and W. Dyatmiko, Helv. Chim. Acta, 80, 1144 (1997); https://doi.org/10.1002/hlca.19970800411.
- R.J. Ruch, S.J. Cheng and J.E. Klaunig, Carcinogenesis, 10, 1003 (1989); https://doi.org/10.1093/carcin/10.6.1003.
- L.C. Green, D.A. Wagner, J. Glogowski, P.L. Skipper, J.S. Wishnok and S.R. Tannenbaum, Anal. Biochem., 126, 131 (1982); https://doi.org/10.1016/0003-2697(82)90118-X.
- L. Marcocci, J.J. Maguire, M.T. Droy-Lefaix and L. Packer, Biochem. Biophys. Res. Commun., 201, 748 (1994); https://doi.org/10.1006/bbrc.1994.1764.
References
J.A. Sikorski, M.J. Miller, D.S. Braccolino, D.G. Cleary, S.D. Corey, J.L. Font, K.J. Gruys, C.Y. Han, K.-C. Lin, P.D. Pansegrau, J.E. Ream, D. Schnur, A. Shah and M.C. Walker, Phosphorus Sulfur Silicon Rel. Elem., 76, 115 (1993); https://doi.org/10.1080/10426509308032372.
L. Maier and H. Spörri, Phosphorus Sulfur Silicon Rel. Elem., 61, 69 (1991); https://doi.org/10.1080/10426509108027339.
J. Emsley and D. Hall, In Chemistry of Phosphorus, Harper & Row: London, p. 494 (1976).
F.R. Atherton, C.H. Hassall and R.W. Lambert, J. Med. Chem., 29, 29 (1986); https://doi.org/10.1021/jm00151a005.
P. Kafarski and B. Lejczak, Phosphorus Sulfur Silicon Rel. Elem., 63, 193 (1991); https://doi.org/10.1080/10426509108029443.
C.-W. Guo, S.-H. Wu, F.-L. Chen, Z.-Y. Han, X.-H. Fu and R. Wan, Phosphorus Sulfur Silicon Rel. Elem., 191, 1250 (2016); https://doi.org/10.1080/10426507.2016.1166365.
H.L. Wang, J. Zhou, Y.G. Qiu, K.S. Feng and R.Y. Chen, Phosphorus Sulfur Silicon Rel. Elem., 104, 135 (1995); https://doi.org/10.1080/10426509508042585.
J. Zhou, R.Y. Chen and X.F. Yang, Heteroatom Chem., 9, 369 (1998); https://doi.org/10.1002/(SICI)1098-1071(1998)9:4<369::AIDHC4>3.0.CO;2-3.
A.B. Smith III, C.M. Taylor, S.J. Benkovic and R. Hirschmann, Tetrahedron Lett., 35, 6853 (1994); https://doi.org/10.1016/0040-4039(94)85022-4.
G.F. Makhaeva, V.V. Malygin, A.Y. Aksinenko, V.B. Sokolov, N.N. Strakhova, A.N. Rasdolsky, R.J. Richardson and I.V. Martynov, Dokl. Biochem. Biophys., 400, 92 (2005); https://doi.org/10.1007/s10628-005-0041-7.
W. Pan, C. Ansiaux and S.P. Vincent, Tetrahedron Lett., 48, 4353 (2007); https://doi.org/10.1016/j.tetlet.2007.04.113.
E.K. Baylis, C.D. Campbell and J.G. Dingwall, J. Chem. Soc. Perkin Trans. I, 2845 (1984); https://doi.org/10.1039/p19840002845.
M.C. Allen, W. Fuhrer, B. Tuck, R. Wade and J.M. Wood, J. Med. Chem., 32, 1652 (1989); https://doi.org/10.1021/jm00127a041.
B.V.S. Reddy, A.S. Krishna, A.V. Ganesh and G.G.K.S.N. Kumar, Tetrahedron Lett., 52, 1359 (2011); https://doi.org/10.1016/j.tetlet.2011.01.074.
J. Tang, L. Wang, W. Wang, L. Zhang, S. Wu and D. Mao, J. Fluor. Chem., 132, 102 (2011); https://doi.org/10.1016/j.jfluchem.2010.12.002.
Z. Karimi-Jaberi, H. Zare, M. Amiri and N. Sadeghi, Chin. Chem. Lett., 22, 559 (2011); https://doi.org/10.1016/j.cclet.2010.11.034.
H. Firouzabadi, N. Iranpoor and S. Sobhani, Synthesis, 2692 (2004); https://doi.org/10.1055/s-2004-831251.
S. Bhagat and A.K. Chakraborti, J. Org. Chem., 72, 1263 (2007); https://doi.org/10.1021/jo062140i.
Ambica, S. Kumar, S.C. Taneja, M.S. Hundal and K.K. Kapoor, Tetrahedron Lett., 49, 2208 (2008); https://doi.org/10.1016/j.tetlet.2008.02.047.
A.S. Paraskar and A. Sudalai, ARKIVOC, 183 (2006); https://doi.org/10.3998/ark.5550190.0007.a21.
Z.P. Zhan and J.P. Li, Synth. Commun., 35, 2501 (2005); https://doi.org/10.1080/00397910500212692.
R. Ghosh, S. Maiti, A. Chakraborty and D. Maiti, J. Mol. Catal. Chem., 210, 53 (2004); https://doi.org/10.1016/j.molcata.2003.09.020.
P.P. Sun, Z.X. Hu and Z.H. Huang, Synth. Commun., 34, 4293 (2004); https://doi.org/10.1081/SCC-200039361.
S.A. Sadaphal, S.S. Sonar, A.H. Kategaonkar and M.S. Shingare, Bull. Korean Chem. Soc., 30, 1054 (2009); https://doi.org/10.5012/bkcs.2009.30.5.1054.
J.S. Yadav, B.V.S. Reddy and P. Sreedhar, Green Chem., 4, 436 (2002); https://doi.org/10.1039/B203934F.
S. Lee, J.K. Lee, C.E. Song and D.C. Kim, Bull. Korean Chem. Soc., 23, 667 (2002); https://doi.org/10.5012/bkcs.2002.23.5.667.
S. Lee, J.H. Park, J.K. Lee and J. Kang, Chem. Commun., 1698 (2001); https://doi.org/10.1039/b104967b.
S. Chandrasekhar, C. Narsihmulu, S.S. Sultana, B. Saritha and S.J. Prakash, Synlett, 505 (2003); https://doi.org/10.1055/s-2003-37508.
J.H. Clark and C.N. Rhodes, Clean Synthesis using Porous Inorganic Solid Catalysts and Supported Reagents, Royal Society of Chemistry: Cambridge (2000).
V.S. Gerard and F. Notheisz, Heterogeneous Catalysis in Organic Chemistry, Elsevier: San Diego (2000).
E. Rafiee, S. Rashidzadeh and A. Azad, J. Mol. Catal. Chem., 261, 49 (2007); https://doi.org/10.1016/j.molcata.2006.07.058.
A. Davoodnia, M. Bakavoli, G. Barakouhi and N. Tavakoli Hoseini, Chin. Chem. Lett., 18, 1483 (2007); https://doi.org/10.1016/j.cclet.2007.10.013.
N. Tavakoli-Hoseini and A. Davoodnia, Asian J. Chem., 22, 7197 (2010).
A. Davoodnia, A. Tavakoli-Nishaburi and T.-H. Niloofar, Bull. Korean Chem. Soc., 32, 635 (2011); https://doi.org/10.5012/bkcs.2011.32.2.635.
A. Corma and H. Garcia, Adv. Synth. Catal., 348, 1391 (2006); https://doi.org/10.1002/adsc.200606192.
K. Niknam, B. Karami and M.A. Zolfigol, Catal. Commun., 8, 1427 (2007); https://doi.org/10.1016/j.catcom.2006.12.011.
K. Niknam, M.A. Zolfigol, A. Khorramabadi-Zad, R. Zare and M. Shayegh, Catal. Commun., 7, 494 (2006); https://doi.org/10.1016/j.catcom.2006.01.004.
I.V. Kozhevinkov, Catalysis by Poly Oxometalates; Wiley: Chichester, pp 2-22 (2002).
A.R. Hajipour and A.E. Ruoho, Tetrahedron Lett., 46, 8307 (2005); https://doi.org/10.1016/j.tetlet.2005.09.178.
S. Kantevari, R. Bantu and L. Nagarapu, J. Mol. Catal. Chem., 269, 53 (2007); https://doi.org/10.1016/j.molcata.2006.12.039.
A. Davoodnia, M. Roshani, S.H. Malaeke and M. Bakavoli, Chin. Chem. Lett., 19, 525 (2008); https://doi.org/10.1016/j.cclet.2008.01.037.
A.T. Khan, S. Ghosh and L.H. Choudhury, Eur. J. Org. Chem., 9, 2226 (2006); https://doi.org/10.1002/ejoc.200600006.
M.Z. Dastmalbaf, A. Davoodnia, M.M. Heravi, N. Tavakoli Hoseini, A. Khojastehnezhad and H.A. Zamani, Bull. Korean Chem. Soc., 32, 656 (2011); https://doi.org/10.5012/bkcs.2011.32.2.656.
A. Khojastehnezhad, A. Davoodnia, M. Bakavoli, N. Tavakoli-Hoseini and M. Zeinali-Dastmalbaf, Chin. J. Chem., 29, 297 (2011); https://doi.org/10.1002/cjoc.201190081.
H. Li, X. Yu, S.-T. Tu, J. Yan and Z. Wang, J. Appl. Catal. A, 387, 215 (2010); https://doi.org/10.1016/j.apcata.2010.08.030.
A. Emrani, A. Davoodnia and N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 32, 2385 (2011); https://doi.org/10.5012/bkcs.2011.32.7.2385.
G. Sravya, G.V. Zyryanov, A. Balakrishna, K.M. Kumar Reddy, C.S. Reddy, G.M. Reddy, A. Camilo Jr., J.R. Garcia and N.B. Reddy, Phosphorus, Sulfur Silicon Rel. Elem., 193, 562 (2018); https://doi.org/10.1080/10426507.2018.1455201.
M. Burits and F. Bucar, Phytother. Res., 14, 323 (2000); https://doi.org/10.1002/1099-1573(200008)14:5<323::AIDPTR621>3.0.CO;2-Q.
M. Cuendet, K. Hostettmann, O. Potterat and W. Dyatmiko, Helv. Chim. Acta, 80, 1144 (1997); https://doi.org/10.1002/hlca.19970800411.
R.J. Ruch, S.J. Cheng and J.E. Klaunig, Carcinogenesis, 10, 1003 (1989); https://doi.org/10.1093/carcin/10.6.1003.
L.C. Green, D.A. Wagner, J. Glogowski, P.L. Skipper, J.S. Wishnok and S.R. Tannenbaum, Anal. Biochem., 126, 131 (1982); https://doi.org/10.1016/0003-2697(82)90118-X.
L. Marcocci, J.J. Maguire, M.T. Droy-Lefaix and L. Packer, Biochem. Biophys. Res. Commun., 201, 748 (1994); https://doi.org/10.1006/bbrc.1994.1764.