RESEARCH ARTICLE

 

One-pot synthesis of substituted pyrroles with N,N,N',N' -tetrachlorobenzene-1,3-disulphonamide and N,N'-diiodo-N,N'-1,2-ethanediylbis (p-toluenesulphonamide) as novel catalytic reagents

 

 

Ramin Ghorbani-Vaghei; Hojat Veisi

Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamadan 65174, Iran

 

 

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ABSTRACT

In this research, N_/N_/N',N'-tetrachlorobenzene-1,3-disulphonamide as novel catalytic reagent and N,N'-diiodo-N,N'-1,2-ethanediylbis(p-toluenesulphonamide) as new catalyst were used for the synthesis of N-substituted pyrroles in good to excellent yields under mild conditions. These reusable reagents were compared with existing reagents and it is clear that this study is a welcome addition in the field of pyrrole synthesis.

Keywords: Pyrroles, Paal-Knorr reaction, TCBDA, NIBTS, catalytic reagent

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Full text available only in PDF format.

 

Acknowledgements

We are thankful to the Bu-Ali Sina University, Center of Excellence and Development of Chemical Methods (CEDCM) for financial support and to the University of Sheffield for the NMR and mass spectra and CHN analyses. One of the authors (RG-V) acknowledges Prof. I. Coldham from the University of Sheffield for his kindness in hosting him as a research visitor. We heartily thank Dr Saeed Khodabakhsh for editing the manuscript.

 

References

1 B.C. Ranu, A. Hajra and C. Jana, Synlett, 2000, 75-79.         [ Links ]

2 B.K. Banik, S. Samajdar and I. Banik, J. Org. Chem., 2004, 69, 213-216.         [ Links ]

3 T.N. Danks, Tetrahedron Lett, 1999, 40, 3957-3960.         [ Links ]

4 H.S.P. Rao, S. Jothilingam and H.W. Scheeren, Tetrahedron, 2004, 60, 1625-1630.         [ Links ]

5 B.K. Banik, I. Banik, M. Renteria and S.K. Dasgupta, Tetrahedron Lett., 2005, 46, 2643-2645.         [ Links ]

6 J. Chen, H. Wu, Z. Zheng, C. Jin, X. Zhang and W. Su, Tetrahedron Lett., 2006, 47, 5383-5387.         [ Links ]

7 J.J. Klappa, A.E. Rich and K. McNeill, Org. Lett., 2002, 4, 435-437.         [ Links ]

8 M. Curini, F. Montanari, O. Rosati, E. Lioy and R. Margarita, Tetrahedron Lett., 2003, 44, 3923-3925.         [ Links ]

9 A. Furstner, H. Weintritt and A. Hupperts, J. Org. Chem., 1995, 60, 6637-6641.         [ Links ]

10 M. Periasamy, G. Srinivas and P. Baharathi, J. Org. Chem., 1999, 64, 4204-4205.         [ Links ]

11 R.K. Dieter and H. Yu, Org. Lett., 2000, 2, 2283-2286 and references therein.         [ Links ]

12 A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253-15272.         [ Links ]

13 C.F. Lee, L.M. Yang, T.Y. Hwu, A.S. Feng, J.C. Tsengand T.Y. Luh, J. Am. Chem. Soc., 2000, 122, 4992-4993.         [ Links ]

14 G. Dou, C. Shi and D. Shi, J. Comb. Chem., 2008, 10, 810-813.         [ Links ]

15 A.R. Bharadwaj and K.A. Scheidt, Org. Lett., 2004, 6, 2465-2468.         [ Links ]

16 A. Katritzky, J. Jiang and P.J. Steel, J. Org. Chem, 1994, 59, 4551-4555.         [ Links ]

17 R. Ghorbani-Vaghei, Tetrahedron Lett., 2003, 44, 7529-7532.         [ Links ]

18 R. Ghorbani-Vaghei, E. Shahbazee and H. Veisi, Mendeleev Commun., 2005, 207-208.         [ Links ]

19 R. Ghorbani-Vaghei and H. Jalili, Synthesis, 2005, 1099-1102.         [ Links ]

20 R. Ghorbani-Vaghei, M.A. Zolfigol, M. Chegeny and H. Veisi, Tetrahedron Lett., 2006, 47, 4505-4508.         [ Links ]

21 R. Ghorbani-Vaghei and E. Shahbazee, J. Braz. Chem. Soc., 2005, 16, 647-649.         [ Links ]

22 M.A. Zolfigol, R. Ghorbani-Vaghei, S. Mallakpour, G. Chehardoli, A. Ghorbani-Choghamarani and A.H. Yazdi, Synthesis, 2006, 1631-1634.         [ Links ]

23 R. Ghorbani-Vaghei, D. Azarifar and B. Maleki, Bull. Korean Chem. Soc., 2004, 25, 953-954.         [ Links ]

24 V. Amarnath, D.C. Anthony, K. Amarnath, W.M. Valentine, L.A. Wetterau and G. Graham, J. Org. Chem., 1991, 56, 6924-6931.         [ Links ]

25 Z.-H. Zhang, J.-J. Li and T.-S. Li, Ultrasonics Sonochemistry, 2008, 15, 673-676.         [ Links ]

 

 

Received 6 October 2008
Revised 26 January 2009
Accepted 2 February 2009

 

 

* To whom correspondence should be addressed. E-mail: rgvaghei@yahoo.com