Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Amino Acids Catalyzed Biginelli Protocols
Corresponding Author(s) : Misbahul Ain Khan
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
Various amino acids were found to be excellent catalysts for the Biginelli dihydropyimidone synthesis. The method is simple and provides an alternate and efficient catalyst for the multiple component reactions.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- C.O. Kappa and A. Stadler, Org. React., 63, 1 (2004); C.O. Kappe, Eur. J. Med. Chem., 35, 1043 (2000).
- J. Lu and H. Ma, Synlett, 63 (2000); J. Lu and Y.-H. Bai, Synthesis, 466 (2002); J. Lu, Y.-H. Bai, Y.-H. Guo, Z.-J. Wang and H.-R. Ma, Chin. J. Chem., 20, 681 (2002); R. Fazaeli, S. Tangestaninejad and H. Aliyan, Asian J. Chem., 22, 877 (2010); B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.W. Wang, J.-T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002); Y.-F. Yuan, M.L. Pang, J.-T. Wang and C. Peppe, J. Organomet. Chem., 672, 52 (2003); Ch-V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu and V.N.N. Reddy, Tetrahedron Lett., 43, 2657 (2002); J. Lu, Y.-H. Bay, Z.-J. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); D.S. Bose, L. Fatima and H.B. Mereyala, J. Org. Chem., 68, 587 (2003); D. Russowsky, F.A. Lopes, V.S.S. da Silva, K.F.S. Canto, M.G.M. D'oca and M.N. Godoi, J. Braz. Chem. Soc., 15, 165 (2004); U.B. More, Asian J. Chem., 24, 1906 (2012).
- A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); Z.T. Wang, L.W. Xu and H.Q. Wang, Tetrahedron Lett., 45, 7951 (2004); J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); S.K. De and R. A. Gibbs, Synthesis, 1748 (2005); S.V. Ryabukhin, A.S. Plaskon, E.N. Ostapchuk, D.M. Volochnyuk and A.A. Tolmachev, Synthesis, 417 (2007); J.H. Schauble, E.A. Trauffer, P.P. Deshpande and R.D. Evans, Synthesis, 1333 (2005); J. Lu and H.R. Ma, Synlett, 63 (2000); E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998); Y.Yu, D. Liu and G. Luo, Bioorg. Med. Chem. Lett., 17, 3508 (2007).
- H. Hazarkhani and B. Karimi, Synthesis, 1239 (2004); A. Stadler and C.O. Kappe, J. Chem. Soc. Perkin Trans. I, 1363 (2000); H.A. Stefani and P.M. Gatti, Synth. Commun., 30, 2165 (2000); C.O. Kappe, D. Kumar and R.S. Varma, Synthesis, 1799 (1999); J.J.V. Eynde and A. Mayenee, Molecules, 8, 381 (2003); A. Stadler, B.H. Yonsefi, W.P. Dallinger, E. Vander Eycken, N. Kaval and C.O. Kappe, Org. Process Res. Dev., 7, 707 (2003); A. Stadler and C.O. Kappe, J. Comb. Chem., 3, 624 (2001); M. Rahman, J. Heterocycl. Chem., 47, 1230 (2010).
- J.H. Schauble, E.A. Trauffer, P.P. Deshpande and R.D. Evans, Synthesis, 1333 (2005); S.K. De and R.A. Gibbs, Synthesis, 1748 (2005); M. Abdollahi-Alibeik abd Zaghghi, Chem. Papers, 63, 97 (2009); T. Boumoud, B. Boumoud, S. Rhouati, A. Belfaitah, A. Debache and P. Mosset, Acta Chim. Slov., 55, 617 (2008); D. Song, R. Wang, Y. Chen, S. Zhang, C. Liu and G. Luo, React. Kinet. Catal. Lett., 95, 385 (2008); A. Debache, R. Boulcina, T. Radia, A. Belfaitah, S. Rhouati and B. Carboni, Chin. J. Chem., 26, 2112 (2008); M. Nasr-Esfahani, B. Karami, M. Montazerozohori and A. Karim, J. Heterocycl. Chem., 45, 1183 (2008); H. Valizadeh, H. Gholipur, R. Zarrebin, M. Amir, M.R. Sabzi, Phosphorous Sulfur Silicon Rel. Elem., 183, 1552 (2008); N. Pai, K. Waghmode and D. Khandekar, Asian J. Chem., 23, 5217 (2011); B. Mirza, M. Sargordan and R. Fazaeli, Asian J. Chem., 24, 1421 (2012).
- J. Xin, L. Chang, Z. Hou, D. Shang, X. Liu and X. Feng, Chem. Eur. J., 14, 3177 (2008).
- J. Mabry and B. Ganem, Tetrahedron Lett., 47, 55 (2006).
- M. Bararjanian, S. Balalaie, B. Morassagh and A.M. Amani, Iran. J. Chem., 6, 436 (2009).
- K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 3784 (1933).
- C.O. Kappe, J. Org. Chem., 62, 7201 (1997).
- H.D. Dakin, J. Biol. Chem., 7, 49 (1909); C.A.C. Haley and P. Maitland, J. Chem. Soc., 3155 (1951); F.S. Prout, J. Org. Chem., 18, 928 (1953); J. Diekmann, W.R. Hertler and R. Benson, J. Org. Chem., 28, 2719 (1963); D.B. Ramchary, N.S. Chowdari and C.F. Barbas III, Angew. Chem. Int. Ed., 42, 4233 (2003); Y. Wang, Z.-C. Shang, T.-X. Wu, J.- C. Fan and X. Chen, J. Mol. Catal. A, Chem., 253, 212 (2006).
- K. Folkers, H.J. Harwood and T.B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932).
References
C.O. Kappa and A. Stadler, Org. React., 63, 1 (2004); C.O. Kappe, Eur. J. Med. Chem., 35, 1043 (2000).
J. Lu and H. Ma, Synlett, 63 (2000); J. Lu and Y.-H. Bai, Synthesis, 466 (2002); J. Lu, Y.-H. Bai, Y.-H. Guo, Z.-J. Wang and H.-R. Ma, Chin. J. Chem., 20, 681 (2002); R. Fazaeli, S. Tangestaninejad and H. Aliyan, Asian J. Chem., 22, 877 (2010); B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.W. Wang, J.-T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002); Y.-F. Yuan, M.L. Pang, J.-T. Wang and C. Peppe, J. Organomet. Chem., 672, 52 (2003); Ch-V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu and V.N.N. Reddy, Tetrahedron Lett., 43, 2657 (2002); J. Lu, Y.-H. Bay, Z.-J. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); D.S. Bose, L. Fatima and H.B. Mereyala, J. Org. Chem., 68, 587 (2003); D. Russowsky, F.A. Lopes, V.S.S. da Silva, K.F.S. Canto, M.G.M. D'oca and M.N. Godoi, J. Braz. Chem. Soc., 15, 165 (2004); U.B. More, Asian J. Chem., 24, 1906 (2012).
A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); Z.T. Wang, L.W. Xu and H.Q. Wang, Tetrahedron Lett., 45, 7951 (2004); J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); S.K. De and R. A. Gibbs, Synthesis, 1748 (2005); S.V. Ryabukhin, A.S. Plaskon, E.N. Ostapchuk, D.M. Volochnyuk and A.A. Tolmachev, Synthesis, 417 (2007); J.H. Schauble, E.A. Trauffer, P.P. Deshpande and R.D. Evans, Synthesis, 1333 (2005); J. Lu and H.R. Ma, Synlett, 63 (2000); E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998); Y.Yu, D. Liu and G. Luo, Bioorg. Med. Chem. Lett., 17, 3508 (2007).
H. Hazarkhani and B. Karimi, Synthesis, 1239 (2004); A. Stadler and C.O. Kappe, J. Chem. Soc. Perkin Trans. I, 1363 (2000); H.A. Stefani and P.M. Gatti, Synth. Commun., 30, 2165 (2000); C.O. Kappe, D. Kumar and R.S. Varma, Synthesis, 1799 (1999); J.J.V. Eynde and A. Mayenee, Molecules, 8, 381 (2003); A. Stadler, B.H. Yonsefi, W.P. Dallinger, E. Vander Eycken, N. Kaval and C.O. Kappe, Org. Process Res. Dev., 7, 707 (2003); A. Stadler and C.O. Kappe, J. Comb. Chem., 3, 624 (2001); M. Rahman, J. Heterocycl. Chem., 47, 1230 (2010).
J.H. Schauble, E.A. Trauffer, P.P. Deshpande and R.D. Evans, Synthesis, 1333 (2005); S.K. De and R.A. Gibbs, Synthesis, 1748 (2005); M. Abdollahi-Alibeik abd Zaghghi, Chem. Papers, 63, 97 (2009); T. Boumoud, B. Boumoud, S. Rhouati, A. Belfaitah, A. Debache and P. Mosset, Acta Chim. Slov., 55, 617 (2008); D. Song, R. Wang, Y. Chen, S. Zhang, C. Liu and G. Luo, React. Kinet. Catal. Lett., 95, 385 (2008); A. Debache, R. Boulcina, T. Radia, A. Belfaitah, S. Rhouati and B. Carboni, Chin. J. Chem., 26, 2112 (2008); M. Nasr-Esfahani, B. Karami, M. Montazerozohori and A. Karim, J. Heterocycl. Chem., 45, 1183 (2008); H. Valizadeh, H. Gholipur, R. Zarrebin, M. Amir, M.R. Sabzi, Phosphorous Sulfur Silicon Rel. Elem., 183, 1552 (2008); N. Pai, K. Waghmode and D. Khandekar, Asian J. Chem., 23, 5217 (2011); B. Mirza, M. Sargordan and R. Fazaeli, Asian J. Chem., 24, 1421 (2012).
J. Xin, L. Chang, Z. Hou, D. Shang, X. Liu and X. Feng, Chem. Eur. J., 14, 3177 (2008).
J. Mabry and B. Ganem, Tetrahedron Lett., 47, 55 (2006).
M. Bararjanian, S. Balalaie, B. Morassagh and A.M. Amani, Iran. J. Chem., 6, 436 (2009).
K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 3784 (1933).
C.O. Kappe, J. Org. Chem., 62, 7201 (1997).
H.D. Dakin, J. Biol. Chem., 7, 49 (1909); C.A.C. Haley and P. Maitland, J. Chem. Soc., 3155 (1951); F.S. Prout, J. Org. Chem., 18, 928 (1953); J. Diekmann, W.R. Hertler and R. Benson, J. Org. Chem., 28, 2719 (1963); D.B. Ramchary, N.S. Chowdari and C.F. Barbas III, Angew. Chem. Int. Ed., 42, 4233 (2003); Y. Wang, Z.-C. Shang, T.-X. Wu, J.- C. Fan and X. Chen, J. Mol. Catal. A, Chem., 253, 212 (2006).
K. Folkers, H.J. Harwood and T.B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932).