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A Green Approach to Synthesize Dihydropyrimidinone Derivatives by Using Anhydrous ZnCl2 Catalyst Under Refluxing Condition in Heptane-Toluene Medium via Biginelli Reaction
Corresponding Author(s) : Kawsari Akhter
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
Aldehydes, 1a-g (1a, Ar = 4-Cl-C6H4, 1b, Ar = 4-CH3-C6H4, 1c, Ar = 2-Cl-C6H4, 1d, Ar = 2-CH3- C6H4, 1e, Ar = -C6H5, Ar = 4-Cl-C6H4, 1g, Ar = 2-Cl-C6H4) reacted with acetylacetone 2a and urea/thiourea 3a-b in the presence of anhydrous zinc chloride under refluxing condition in heptane-toluene medium to give the corresponding 5-aceto-4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydropyridimidine 4a-d and 5-aceto-4-aryl-6-methyl-2-thio-1,2,3,4-tetrahydropyridimidine 4e-g. The structure of the compounds 4a-g were confirmed by their UV, IR, 1H NMR and 13C NMR analysis.
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- C.O. Kappe, Tetrahedron, 49, 6937 (1993); doi:10.1016/S0040-4020(01)87971-0.
- C.O. Kappe, D. Kumar and R.S. Varma, Synthesis, 1799 (1999); doi:10.1055/s-1999-3592.
- (a) K.S. Atwal, G.C. Rovnyak, B.C. O’Reilly and J. Schwartz, J. Org. Chem., 54, 5898 (1989); doi:10.1021/jo00286a020; (b) K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg and B.C. O’Reilly, J. Med. Chem., 34, 806 (1991); doi:10.1021/jm00106a048; (c) G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz and M.F. Malley, J. Med. Chem., 35, 3254 (1992); doi:10.1021/jm00095a023; (d) C.O. Kappe, W.M.F. Fabian and M.A. Semones, Tetrahedron, 53, 2803 (1997); doi:10.1016/S0040-4020(97)00022-7; (e) K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smillie and M.F. Malley, J. Med. Chem., 33, 2629 (1990); doi:10.1021/jm00171a044.
- (a) E.W. Hurst and R. Hull, J. Med. Pharm. Chem., 3, 215 (1961); doi:10.1021/jm50015a002; (b) H. Cho, M. Ueda, K. Shima, A. Mizuno, M. Hayashimatsu, Y. Ohnaka, Y. Takeuchi, M. Hamaguchi and K. Aisaka, J. Med. Chem., 32, 2399 (1989); doi:10.1021/jm00130a029; (c) G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz and M.F. Malley, J. Med. Chem., 35, 3254 (1992); doi:10.1021/jm00095a023.
- T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber and T.J. Mitchison, Science, 286, 971 (1999); doi:10.1126/science.286.5441.971.
- (a) A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C.D. Brosse, S. Mai, A. Truneh and B. Carte, J. Org. Chem., 60, 1182 (1995); doi:10.1021/jo00110a021; (b) B.B. Snider, J. Chen, A.D. Patil and A. Freyer, Tetrahedron Lett., 37, 6977 (1996); doi:10.1016/0040-4039(96)01575-4.
- L.E. Overman, M.H. Rabinowitz and P.A. Renhowe, J. Am. Chem. Soc., 117, 2657 (1995); doi:10.1021/ja00114a034.
- (a) K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 56, 1180 (1934); doi:10.1021/ja01320a058; (b) K. Folkers, H.J. Harwood and T.B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932); doi:10.1021/ja01348a040; (c) P. Wipf and A. Cunningham, Tetrahedron Lett., 36, 7819 (1995); doi:10.1016/0040-4039(95)01660-A.
- A.D. Shutalev, E.A. Kishko, N. Sivova and A.Y. Kuznetsov, Molecules, 3, 100 (1998); doi:10.3390/30300100.
- F. Bigi, S. Carloni, B. Frullanti, R. Maggi and G. Sartori, Tetrahedron Lett., 40, 3465 (1999); doi:10.1016/S0040-4039(99)00424-4.
- J. Peng and Y. Deng, Tetrahedron Lett., 42, 5917 (2001); doi:10.1016/S0040-4039(01)01139-X.
- J.S. Yadav, B.V.S. Reddy, K. Bhaskar Reddy, K. Sarita Raj and A.R. Prasad, J. Chem. Soc., Perkin Trans. 1, 1939 (2001); doi:10.1039/b102565c.
- (a) E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998); doi:10.1021/jo970846u.; (b) C. Liu, J. Wang and Y.J. Li, Mol. Catal. A, 258, 367 (2006); doi:10.1016/j.molcata.2006.07.037.
- Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000); doi:10.1021/jo9919052.
- J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); doi:10.1016/S0040-4039(00)01645-2.
- B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); doi:10.1021/jo000711f.
References
C.O. Kappe, Tetrahedron, 49, 6937 (1993); doi:10.1016/S0040-4020(01)87971-0.
C.O. Kappe, D. Kumar and R.S. Varma, Synthesis, 1799 (1999); doi:10.1055/s-1999-3592.
(a) K.S. Atwal, G.C. Rovnyak, B.C. O’Reilly and J. Schwartz, J. Org. Chem., 54, 5898 (1989); doi:10.1021/jo00286a020; (b) K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg and B.C. O’Reilly, J. Med. Chem., 34, 806 (1991); doi:10.1021/jm00106a048; (c) G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz and M.F. Malley, J. Med. Chem., 35, 3254 (1992); doi:10.1021/jm00095a023; (d) C.O. Kappe, W.M.F. Fabian and M.A. Semones, Tetrahedron, 53, 2803 (1997); doi:10.1016/S0040-4020(97)00022-7; (e) K.S. Atwal, G.C. Rovnyak, S.D. Kimball, D.M. Floyd, S. Moreland, B.N. Swanson, J.Z. Gougoutas, J. Schwartz, K.M. Smillie and M.F. Malley, J. Med. Chem., 33, 2629 (1990); doi:10.1021/jm00171a044.
(a) E.W. Hurst and R. Hull, J. Med. Pharm. Chem., 3, 215 (1961); doi:10.1021/jm50015a002; (b) H. Cho, M. Ueda, K. Shima, A. Mizuno, M. Hayashimatsu, Y. Ohnaka, Y. Takeuchi, M. Hamaguchi and K. Aisaka, J. Med. Chem., 32, 2399 (1989); doi:10.1021/jm00130a029; (c) G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz and M.F. Malley, J. Med. Chem., 35, 3254 (1992); doi:10.1021/jm00095a023.
T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber and T.J. Mitchison, Science, 286, 971 (1999); doi:10.1126/science.286.5441.971.
(a) A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C.D. Brosse, S. Mai, A. Truneh and B. Carte, J. Org. Chem., 60, 1182 (1995); doi:10.1021/jo00110a021; (b) B.B. Snider, J. Chen, A.D. Patil and A. Freyer, Tetrahedron Lett., 37, 6977 (1996); doi:10.1016/0040-4039(96)01575-4.
L.E. Overman, M.H. Rabinowitz and P.A. Renhowe, J. Am. Chem. Soc., 117, 2657 (1995); doi:10.1021/ja00114a034.
(a) K. Folkers and T.B. Johnson, J. Am. Chem. Soc., 56, 1180 (1934); doi:10.1021/ja01320a058; (b) K. Folkers, H.J. Harwood and T.B. Johnson, J. Am. Chem. Soc., 54, 3751 (1932); doi:10.1021/ja01348a040; (c) P. Wipf and A. Cunningham, Tetrahedron Lett., 36, 7819 (1995); doi:10.1016/0040-4039(95)01660-A.
A.D. Shutalev, E.A. Kishko, N. Sivova and A.Y. Kuznetsov, Molecules, 3, 100 (1998); doi:10.3390/30300100.
F. Bigi, S. Carloni, B. Frullanti, R. Maggi and G. Sartori, Tetrahedron Lett., 40, 3465 (1999); doi:10.1016/S0040-4039(99)00424-4.
J. Peng and Y. Deng, Tetrahedron Lett., 42, 5917 (2001); doi:10.1016/S0040-4039(01)01139-X.
J.S. Yadav, B.V.S. Reddy, K. Bhaskar Reddy, K. Sarita Raj and A.R. Prasad, J. Chem. Soc., Perkin Trans. 1, 1939 (2001); doi:10.1039/b102565c.
(a) E.H. Hu, D.R. Sidler and U.H. Dolling, J. Org. Chem., 63, 3454 (1998); doi:10.1021/jo970846u.; (b) C. Liu, J. Wang and Y.J. Li, Mol. Catal. A, 258, 367 (2006); doi:10.1016/j.molcata.2006.07.037.
Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 65, 3864 (2000); doi:10.1021/jo9919052.
J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 41, 9075 (2000); doi:10.1016/S0040-4039(00)01645-2.
B.C. Ranu, A. Hajra and U. Jana, J. Org. Chem., 65, 6270 (2000); doi:10.1021/jo000711f.