SHORT COMMUNICATION

 

Poly(ethylene)glycol/AlCl₃ as a green and reusable system in the synthesis of α,α'-bis(substituted-benzylidene) cycloalkanones

 

 

Ali Amoozadeh^*; Salman Rahmani; Firouzeh Nemati

Department of Chemistry, Faculty of Science, Semnan University, Semnan, Iran

 

 

---

ABSTRACT

Aluminum chloride has been found to be a highly efficient catalyst for the aldol condensation of aldehydes and cycloketones in poly(ethylene)glycol 400 at room temperature. The reaction is very fast, clean and environmentally benign for the synthesis of a variety of α,α'-bis(substituted-benzylidene) cycloalkanones.

Keywords: Aluminum chloride, poly(ethylene)glycol, α,α'-bis(substituted-benzylidene) cycloalkanones, aldol condensation

---

 

 

Full text available only in PDF format.

 

Acknowledgements

We thank the Department of Chemistry of Semnan University for supporting this work.

 

References

1 J. Deil, T. Lorand, D. Szabo and A. Foldesi, Pharmazie, 1984, 39, 539-540.         [ Links ]

2 J. Kawamata, K. Inoue, T. Inabe, M. Kiguchi, M. Kato and Y. Taniguchi, Chem. Phys. Lett., 1996, 249, 29-34.         [ Links ]

3 J.R.A. Dimmock, M.P. Padmanilayam, G.A. Zello, K.H. Nienaber, T.M. Allen, C.L. Santos, E. de Clercq, J. Balzarini, E.K. Manavathu and J.P. Stables, Eur. J. Med. Chem., 2003, 38, 169-177.         [ Links ]

4 K.K. Gangadhara, Polymer, 1995, 36, 1903-1910.         [ Links ]

5 (a) M. Ogawa, Y. Ishili, T. Nakano and S. Irifune, Japan Kohai Tokyo JP 63192446 A2, 1988;         [ Links ] (b) M. Ogawa, Y. Ishili, T. Nakano and S. Irifune, Chem. Abstr., 1988, 63, 238034.         [ Links ]

6 M. Artico, R.D. Santo, R. Costi, E. Novellino, G. Greco, S. Massa, E. Tramontano, M.F. Marogiu, A.D. Montis and P.L. Colla, J. Med. Chem., 1998, 41, 3948-3960.         [ Links ]

7 R. Costi, R.D. Santo, M. Artico, S. Massa, R. Ragno, R. Loddo, M.L. Colla, E. Tramontano, P.L. Colla and A. Pani, Bioorg. Med. Chem., 2004, 12, 199-215.         [ Links ]

8 B.A. Hathaway, J. Chem. Educ., 1987, 64, 367-368.         [ Links ]

9 T. Nakano, S. Irifune, S. Umano, A. Inada, Y. Ishii and M. Ogawa, J. Org. Chem., 1987, 52, 2239-2244.         [ Links ]

10 K. Watanabe, Bull. Chem. Soc. Japan, 1980, 53, 1366-1371.         [ Links ]

11 (a) M.A. Bigdeli, F. Nemati and G.H. Mahdavinia, Tetrahedron Lett., 2007, 48, 6801-6804;         [ Links ] (b) M.A. Bigdeli, M. M. Heravi and F. Nemati, Synth. Commun., 2007, 2225-2230;         [ Links ] (c) M.A. Bigdeli, H. Dostmohammadi, G.H. Mahdavinia and F. Nemati, J. Heterocycl. Chem., 2008, 45, 1203-1205;         [ Links ] (d) M.A. Bigdeli, M.M. Heravi, F. Nemati and G.H. Mahdavinia, Arkivoc, 2008, 243-248;         [ Links ] (e) A. Amoozadeh and F. Nemati, S. Afr. J. Chem., 2009, 62, 44-46;         [ Links ] (f) A. Amoozadeh and F. Nemati, Phosphorus, Sulfur, Silicon, Relat. Elem., 2009, 184, 2569-2575;         [ Links ] (g) A. Amoozadeh and F. Nemati, Phosphorus, Sulfur, Silicon, Relat. Elem., in press.         [ Links ]

12 S. Chandrasekhar, C. Narshimulu, N.R. Reddy and S.S. Sultana, Tetrahedron Lett, 2004, 45, 4581-4582.         [ Links ]

13 W. Yi and C. Cai, J. Fluorine Chem., 2005, 126, 1553-1558.         [ Links ]

14 S. Bhagat, R. Sharma and A.K. Chakraborti, J. Mol. Catal. A: Chem., 2006, 260, 235-240.         [ Links ]

15 M.A. Bigdeli, G.H. Mahdavinia, S. Jafari and H. Hazarkhani, Catal. Commun, 2007, 8, 2229-2231.         [ Links ]

16 L. Wang, J. Sheng, H. Tian, J. Han, Z. Fan and C. Qian, Synthesis, 2004, 3060-3064.         [ Links ]

17 N. Singh, J. Pandey, A. Yadav, V Chaturvedi, S. Bhatnagar, A.N. Gaikwad, S. K. Sinha, A. Kumar and P.K. Tripathi, Eur. J. Med. Chem., 2009,44, 1705-1709.         [ Links ]

18 A.F.M.M. Rahman, B.S. Jeong, D.H. Kim, J.K. Park, E.S. Lee and Y. Jahng, Tetrahedron Lett., 2007, 63, 2426-2431.         [ Links ]

19 L. An, J. Zou and L. Zhang, Catal. Commun, 2008, 9, 349-354.         [ Links ]

20 B. Das, P. Thirupathi, I. Mahender and K.R. Reddy, J. Mol. Catal. A: Chem., 2006, 247, 182-185.         [ Links ]

 

 

Received 17 October 2009
Revised 22 May 2010
Accepted 31 May 2010

 

 

* To whom correspondence should be addressed. E-mail: aliamoozadeh@yahoo.com, aamozadeh@semnan.ac.ir