SciELO - Scientific Electronic Library Online

 
vol.63Degradation of endosulfan I and endosulfan II in the aquatic environment: A proposed enzymatic kinetic model that takes into account adsorption/desorption of the pesticide by colloidal and/or sediment particlesPh3P catalyzed synthesis of alkyl 2-(4-oxopyridin-1(4H)-yl)acrylates by nucleophilic addition to alkyl propiolates índice de autoresíndice de materiabúsqueda de artículos
Home Pagelista alfabética de revistas  

Servicios Personalizados

Articulo

Indicadores

Links relacionados

  • En proceso de indezaciónCitado por Google
  • En proceso de indezaciónSimilares en Google

Compartir


South African Journal of Chemistry

versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350

S.Afr.j.chem. (Online) vol.63  Durban  2010

 

SHORT COMMUNICATION

 

An environmentally friendly solvent-free synthesis of 3,4-dihydropyrimidinones using a p-aminobenzene sulfonic acid catalyzed Biginelli reaction

 

 

Ming Shu WuI,II, *; Ping HeII; Xiang Zhu ZhangI

IDepartment of Chemical Engineering, Institute of Anyang Technology, Anyang, 455000, Henan, P.R. China
IIDepartment of Chemistry, Hainan Normal University, Haikou 571158, Hainan, P.R. China

 

 


ABSTRACT

Anhydrous p-aminobenzene sulphonic acid mediated solvent-free protocol is described for the synthesis of dihydropyrimidi-nones by the cyclocondensation of aldehydes, β-ketoesters and urea/thiourea. Yields obtained are significantly higher than those obtained utilizing classical Biginelli reaction conditions.

Keywords: Anhydrous p-aminobenzene sulphonic acid, 3,4-dihydropyrimidinones, Biginelli reaction


 

 

Full text available only in PDF format.

 

 

References

1 D.J. Ramon and M. Yus, Angew. Chem. Int. Ed., 2005, 44, 1602-1634.         [ Links ]

2 P. Biginelli, Gazz. Chim. Ital., 1893, 23, 360-416.         [ Links ]

3 K. Folker, H.J. Harwood and T.B. Johnson, J. Am. Chem. Soc., 1932, 54, 3751.         [ Links ]

4 (a) C.O. Kappe, Eur. J. Med. Chem., 2000, 35, 1043-1052;         [ Links ] (b) C.O. Kappe, Tetrahedron, 1993, 49, 6937-6963 ;         [ Links ] (c) C.O. Kappe, Molecules, 1998, 3, 1-9;         [ Links ] (d) C.O. Kappe, Acc. Chem. Res., 2000, 33, 879-888;         [ Links ] (e) B.K. Banik, A.T. Reddy, A. Datta and C. Mukhopadhyay, Tetrahedron Lett., 2007, 48, 7392-7394;         [ Links ] (f) V. Polshettiwar and R.S. Varma, Tetrahedron Lett., 2007, 48, 7343-7346;         [ Links ] (g) H.S.Chandak, N.P. Lad and P.P. Upare, Catal. Lett., 2009, 131, 469-473.         [ Links ]

5 D. Russowsky, R.F.S. Canto, S.A.A. Sanches, M.G.M. D'oca, A.D. Fatima and J.E.D. Carvalho, Bioorg. Chem., 2006, 34, 173-178.         [ Links ]

6 B.B. Snider and Z. Shi, J. Org. Chem., 1993, 58, 3828-3839.         [ Links ]

7 A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, FA. J. Reyer, C. De Brosse, S. Mai, T.A. Runeh and D.J. Faulkner, J. Org. Chem., 1995, 60, 1182-1188.         [ Links ]

8 J. Barluenga, M. Thomas, A. Ballesterus and A. Lopez, Tetrahedron Lett., 1989, 30, 4573^576.         [ Links ]

9 N.Y. Fu, Y.F. Yuan, Z. Cao, S.W. Wang, J.T. Wang and C. Peppe, Tetrahedron, 2002, 58, 4801-4807.         [ Links ]

10 B. Ranu, A. Hajra and J.U. Ana, J. Org. Chem, 2000, 65, 6270-6272.         [ Links ]

11 J.S. Yadav, B.VS. Reddy, R. Srinivas, C. Venugopal and T. Ramalingam, Synthesis, 2001, 1341-1345.         [ Links ]

12 J. Lu, Synthesis, 2002, 466-470        [ Links ]

13 T. Jin and S. Zhang, T. Li, Synth. Commun., 2002, 32, 1847-1851.         [ Links ]

14 J. Lu, Y. Bai, Z. Wang, B. Yang and H. Ma, Tetrahedron Lett., 2000, 41, 9075-9078.         [ Links ]

15 R. Varala, M.M. Alam and S.R. Adapa, Synlett., 2003, 67-70.         [ Links ]

16 Y. Ma, C. Qian, L. Wang and M. Yang, J. Org. Chem., 2000, 65, 3864-3868.         [ Links ]

17 E.H. Hu, D.R. Slider and U.H. Dolling, J. Org. Chem., 1998, 63, 3454-3457.         [ Links ]

18 J. Eng, Y. Deng, Tetrahedron Lett, 2001, 42, 5917-5919.         [ Links ]

19 M. Ajbakhsh, B. Mohajerani, M.M. Heravi and A.N. Ahmadi, J. Mol. Catal. A, 2005, 236, 216-219.         [ Links ]

20 K.V.N. Srinvas and B. Dash, Synthesis, 2004, 2091-2093.         [ Links ]

21 H. Hazarkhani and B. Karimi, Synthesis, 2004, 1239-1242.         [ Links ]

22 B. Gangadasu, S. Palaniappan and VJ. Rao, Synlett., 2004, 1285-1287.         [ Links ]

23 J.K. Joseph, S.L. Jain and B. Sain, J. Mol. Catal. A, 2006, 247, 99-102.         [ Links ]

24 S.P. Maradur and G.S. Gokavi, Catal. Commun, 2007, 8, 279-284.         [ Links ]

25 D. Kumar, M.S. Sundaree and B.G. Mishra, Chem. Lett., 2006, 35, 1074-1075.         [ Links ]

26 C. Liu, J. Wang and Y. Li, J. Mol. Catal. A, 2006, 258, 367-370.         [ Links ]

27 T. Jin, S. Zhang, S. Zhang, J. Guo and T. Li, J. Chem. Res. (s), 2002, 37-39.         [ Links ]

28 K. Rosi Reddy, Ch. Venkateshwar Reddy, M. Mahesh, P.VK. Raju and VV. Narayana Reddy, Tetrahedron Lett., 2003, 44, 8173-8176.         [ Links ]

29 R. Gupta, S. Paul and R. Gupta J. Mol. Catal. A, 2007, 266, 50-53.         [ Links ]

30 H. Sharghia and M. Jokara, Synth. Commun, 2009, 39, 958-979.         [ Links ]

 

 

Received 28 June 2010
Revised 5 August 2010
Accepted19 August 2010

 

 

* To whom correspondence should be addressed. E-mail: wumingshu@126.com

Creative Commons License Todo el contenido de esta revista, excepto dónde está identificado, está bajo una Licencia Creative Commons