SciELO - Scientific Electronic Library Online

 
vol.63Effects of copper exchange levels on complexation of ammonia in Cu (II)-exchanged X zeolite índice de autoresíndice de assuntospesquisa de artigos
Home Pagelista alfabética de periódicos  

Serviços Personalizados

Artigo

Indicadores

Links relacionados

  • Em processo de indexaçãoCitado por Google
  • Em processo de indexaçãoSimilares em Google

Compartilhar


South African Journal of Chemistry

versão On-line ISSN 1996-840X
versão impressa ISSN 0379-4350

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

 

RESEARCH ARTICLE

 

Cyclohexenones through addition of ethyl acetoacetate to 3-aryl-1-(thiophen-3-yl)prop-2-en-1-one derivatives

 

 

Yakup Budak*; Esra Findik; Mustafa Ceylan

Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat 60250, Turkey

 

 


ABSTRACT

Chalcone derivatives 3a-i: containing a thiophene ring were prepared by the condensation of 1-(thiophen-3-yl)ethanone with aromatic aldehydes in excellent yields. The Michael addition of ethyl acetoacetate 4 to chalcone derivatives 3a-i: resulted in the formation of nine novel ethyl 6-aryl-4-(3-thienyl)cyclohex-3-en-2-one-1-carboxylate derivatives 6a-i

Keywords: Michael addition, ethyl acetoacetate, cyclohexenones, cyclocondensation


 

 

Full text available only in PDF format.

 

Acknowledgements

The authors are indebted to the Department of Chemistry (Gaziosmanpasa University) and the Scientific and Technical Research Council of Turkey (Grant TUBITAK-TBAG (106T103)) for financial support.

 

References

1 R.W. Helmkamp, L.J. Tanghe, J. John and J.T. Plati, J. Am. Chem. Soc., 1940, 62, 3215-3219.         [ Links ]

2 E.P. Kohler and C.S. Dewey, J. Am. Chem. Soc., 1924, 46, 1267-1271.         [ Links ]

3 D.B. Reddy, M.VR. Reddy and V Padmavathi, Indian J. Chem., 1997, 36B, 923-927.         [ Links ]

4 D.B. Reddy, V. Padmavathi and B. Seenaiah, Org. Prep. Proc. Int., 1992, 24, 21-24.         [ Links ]

5 W. Borsche, Liebig's Ann, 1910, 375, 145-147.         [ Links ]

6 J.B. Canant, A.H. Bump and H.S. Holt, J. Am. Chem. Soc., 1921, 43, 1677-1684.         [ Links ]

7 E.P. Kohler and R.W. Helmkamp, J. Am. Chem. Soc., 1924, 46, 1018-1024.         [ Links ]

8 D. Loganathan, T. Varghese and G.K. Trivedi, Org. Prep. Proc. Int., 1984, 16, 115-119.         [ Links ]

9 D.B. Reddy, M.VR. Reddy and V Padmavathi, Indian J. Chem., 1998, 37B, 167-169.         [ Links ]

10 H.D. Tabba, N.M. Yousef and M.M. Al-Arab, Coll. Czech. Chem. Commun, 1995, 60, 594-604.         [ Links ]

11 V Padmavathi, K. Sharmila, R.A. Somasekhar and D. Bhaskar, Indian J. Chem., 2001, 40B, 11-14.         [ Links ]

12 D.R. Bhaskar, R. A. Somasekhar and V Padmavathi, J. Chem. Research (S), 1998, 784-785.         [ Links ]

13 V. Padmavathi, R.B.J. Mohan, A. Balaiah, R.K. Venugopal and R.D. Bhaskar, Molecules, 2000, 5, 1281-1286.         [ Links ]

14 V Padmavathi, K. Sharmila, A. Padmaja and R.D. Bhaskar, Heterocycl. Commun., 1999, 5, 451-456.         [ Links ]

15 Y. Hu, X. Liang, J.Wang, Z. Zheng and X. Hu, J. Org. Chem., 2003, 68, 4542-4545.         [ Links ]

16 S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga and M. Shibasaki, J. Am. Chem. Soc., 2003, 125, 2582-2590.         [ Links ]

17 A. Puschl, H. C. Rudbeck, A. Faldt, A. Confante and J. Kehler, Synthesis, 2005, 291-295.         [ Links ]

18 H. Youping, S. Jianqiu and S. Genbo, Acta Cryst., 1994, C50, 804-805.         [ Links ]

19 T. Uchida, K. Kozawa, Y. Kimura and Y. Goto, International Conference of Science and Technology of Synthetic Metals, ICSM '94, Seoul, South Korea,1994.         [ Links ]

20 Y. Namba, M. Saeki and N. Ikawa, CIRP Annals - Manufacturing Technology, 2003, 52, 475-478.         [ Links ]

21 G. Yoshitaka, Nonlinear Opt., Proc. 5th Toyota Conf. Nonlinear Opt. Science, Amsterdam, 1991.         [ Links ]

22 G. Roman, Acta Chim. Slov., 2004, 51, 537-544.         [ Links ]

 

 

Received 27 April 2009
Revised 4 September 200
Accepted 12 November 2009

 

 

* To whom correspondence should be addressed. E-mail: ybudak@gop.edu.tr

Creative Commons License Todo o conteúdo deste periódico, exceto onde está identificado, está licenciado sob uma Licença Creative Commons