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Phenols Catalyzed Biginelli Reactions: A Self Catalyzed Monastrol Protocol
Corresponding Author(s) : Abdul Ghafoor
Asian Journal of Chemistry,
Vol. 28 No. 1 (2016): Vol 28 Issue 1
Abstract
A simple and efficient approach towards one step synthesis of various dihydropyrimidones and thiones (Biginelli reaction) was developed by using phenols as catalysts. The multicomponent reaction was conducted between aromatic aldehydes, active methylenes and urea (or thiourea) in an appropriate solvent. This seems to be a first example, where weak acids such as phenols have been employed with success.
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- C.O. Kappe, Molecules, 3, 1 (1998); doi:10.3390/30100001.
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References
C.O. Kappe, Molecules, 3, 1 (1998); doi:10.3390/30100001.
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T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.I. Schreiber and T. Mitchison, J. Sci., 286, 971 (1999); doi:10.1126/science.286.5441.971.
D.J. Brown, in ed.: A. Weissberger, The Pyridines, Interscience, New York, pp. 183-210 (1962).
E.H. Hu, D.R. Sidler and U.-H. Dolling, J. Org. Chem., 63, 3454 (1998); doi:10.1021/jo970846u.
M.G. Valverde, D. Dallinger and C.O. Kappe, Synlett, 741 (2001); doi:10.1055/s-2001-14608.
K. Ramalinga, P. Vijayalakshmi and T.N.B. Kaimal, Synlett, 863 (2001); doi:10.1055/s-2001-14587.
C.O. Kappe, J. Org. Chem., 62, 7201 (1997); doi:10.1021/jo971010u.
B. Jauk, T. Pernat and C.O. Kappe, Molecules, 5, 227 (2000); doi:10.3390/50300227.
A. Ehsan, Chem. Abstr., 68, 78231 (1967).
J. Peng and Y. Deng, Tetrahedron Lett., 42, 5917 (2001); doi:10.1016/S0040-4039(01)01139-X.
C.O. Kappe, D. Kumar and R.S. Varma, Synthesis, 1799 (1999); doi:10.1055/s-1999-3592.
K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 55, 3784 (1933); doi:10.1021/ja01336a054.
C.O. Kappe, Tetrahedron, 49, 6937 (1993); doi:10.1016/S0040-4020(01)87971-0.
J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); doi:10.1016/S0040-4039(00)01645-2.
J. Lu and H.R. Ma, Synlett, 63 (2000); doi:10.1055/s-2000-6469.
J. Lu and Y. Bai, Synthesis, 466 (2002); doi:10.1055/s-2002-20956.
Y. Ma, C. Qian, L.M. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000); doi:10.1021/jo9919052.
B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); doi:10.1021/jo000711f.
N.Y. Fu, Y.F. Yuan, Z. Cao, S.W. Wang, J.T. Wang and C. Peppe, Tetrahedron, 58, 4801 (2002); doi:10.1016/S0040-4020(02)00455-6.
J.S. Yadav, B.V. Subba Reddy, R. Srinivas, C. Venugopal and T. Ramalingam, Synthesis, 1341 (2001); doi:10.1055/s-2001-15229.
K.A. Kumar, M. Kasthuraiah, C.S. Reddy and C.D. Reddy, Tetrahedron Lett., 42, 7873 (2001); doi:10.1016/S0040-4039(01)01603-3.
C.V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu and V.V.N. Reddy, Tetrahedron Lett., 43, 2657 (2002); doi:10.1016/S0040-4039(02)00280-0.
F. Bigi, S. Carloni, B. Frullanti, R. Maggi and G. Sartori, Tetrahedron Lett., 40, 3465 (1999); doi:10.1016/S0040-4039(99)00424-4.
V.R. Rani, N. Srinivas, M.R. Kishan, S.J. Kulkarni and K.V. Raghavan, Green Chem., 3, 305 (2001); doi:10.1039/b107612b.
J.S. Yadav, B.V.S. Reddy, E.J. Reddy and T. Ramalingam, J. Chem. Res., 354 (2000); doi:10.3184/030823400103167633.
T.S. Jin, S.L. Zhang, S.Y. Zhang, J.J. Guo and T.S. Li, J. Chem. Res., 37 (2002); doi:10.3184/030823402103170394.
A. Stadler and C.O. Kappe, J. Comb. Chem., 3, 624 (2001); doi:10.1021/cc010044j.
J.S. Suresh, ARKIVOC, 66 (2012).
A. Karamat, M.A. Khan and A. Sharif, J. Chin. Chem. Soc., 57, 1099 (2010); doi:10.1002/jccs.201000155.
S. Imtiaz, M.A. Khan, A. Sharif, E. Ahmad, W.O. Lin and M.A. Munawar, J. Chin. Chem. Soc., 59, 1446 (2012); doi:10.1002/jccs.201100472.
A.M. Zafar, S. Qureshi, M.N. Khan, M. Azad, M.A. Munawar and M.A. Khan, Asian J. Chem., 25, 3244 (2013); doi:10.14233/ajchem.2013.13607.
S. Noreen, S. Perveen, M.N. Khan, A. Nazeer, M.A. Khan, M.A. Munawar, R. Babar, F. Sohail, M. Azad, A.M.R. Bernardino and M.S. Dos Santos, Asian J. Chem., 25, 4770 (2013); doi:10.14233/ajchem.2013.14094.
A. Nazeer, Q. Ain, F. Kanwal, M.N. Khan, S. Perveen, H. Amina, W.O. Lin, A. Uzzaman, M. Adnan, M.A. Khan, Affinidad, 72, 20 (2015).
M. Tajbakhsh, Y. Ranjbar, A. Masuodi and S. Khaksar, Chin. J. Catal., 33, 1542 (2012); doi:10.1016/S1872-2067(11)60432-4.
R.J. Kalbasi, A.R. Massah and B. Daneshvarnejad, Appl. Clay Sci., 55, 1 (2012); doi:10.1016/j.clay.2011.05.015.