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South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version ISSN 0379-4350

S.Afr.j.chem. (Online) vol.62  Durban  2009

 

RESEARCH ARTICLE

 

Highly efficient formylation of alcohols, thiols and aniline derivatives by a heterogeneous (HCOOH/SiO2) system under microwave irradiation and solvent-free conditions

 

 

Ramin Ghorbani-VagheiI; Hojat VeisiI; Mostafa AmiriI; Mohammad CheginiI; Mehdi KarimiI; Somayeh Akbari DadamahalehI; Alireza SedrpoushanII

IDepartment of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamadan, Iran
IIChemical Industries Department, Iranian Research Organization for Science and Technology (IROST), P.O. Box 15815-3538, Tehran, Iran

 

 


ABSTRACT

A simple, rapid and efficient microwave-assisted procedure for the formylation of aniline derivatives and alcohols, using a heterogeneous (HCOOH/SiO2) system under solvent-free conditions is reported. The method is applied to a set of amines, alcohols and thiols and short reaction times (<10 min) with high yields are reported. This protocol introduces a practical and viable green technology of solvent-free and catalyst-free reactions.

Keywords: Alcohols, anilines, SiO2, HCOOH, microwave irradiation, solvent-free conditions


 

 

Full text available only in PDF format.

 

Acknowledgement

We are thankful to Bu-Ali Sina University, Center of Excellence and Development of Chemical Methods (CECM) for financial support.

 

References

1 J.C. Sheehan and D.D.H. Yang, J. Am. Chem. Soc., 1958, 80, 1154-1158.         [ Links ]

2 T.W. Green and P.G.M. Wuts, Protective Groups in Organic Synthesis, 3rd edn., Wiley-Interscience, New York, NY, USA,1999.         [ Links ]

3 P. Strazzolini, A.G. Giumanini and S. Cauci, Tetrahedron, 1990, 46, 1081-1118.         [ Links ]

4 F.F. Blicke and C.J. Lu, J. Am. Chem. Soc., 1952, 74, 3933-3934.         [ Links ]

5 J. Waki and J. Meienhofer, J. Org. Chem., 1977, 42, 2019-2020.         [ Links ]

6 F.M.F. Chen and N.L. Benoiton, Synthesis, 1979, 709-713.         [ Links ]

7 H.L. Yale, J. Org. Chem., 1971, 36, 3238-3240.         [ Links ]

8 L. Kisfaludy and O. Laszlo, Synthesis, 1987, 510-513.         [ Links ]

9 M. Neveux, C. Bruneau and P.H. Dixneuf, J. Chem. Soc., Perkin Trans., 1991, 1197-1199.         [ Links ]

10 W. Duczek, J. Deutsch, S. Vieth and H. J. Niclas, Synthesis, 1996, 37-38.         [ Links ]

11 P.G. Reddy, G.D.K. Kumar and S. Baskaran, Tetrahedron Lett., 2000,41, 9149-9151.         [ Links ]

12 S. Treppendhal and P. Jakobsen, Acta Chem. Scand., Ser. B, 1978, 32, 697-700.         [ Links ]

13 S.H. Jung, J.H. Ahn, S.K. Park and J.K. Choi, Bull. Korean Chem. Soc., 2002, 23,149-152.         [ Links ]

14 A. Khoramabadi-Zad, H. Veisi, S.A. Akbari and A. Shiri, J. Chin. Chem. Soc., 2007, 54, 479-481.         [ Links ]

15 K. Ishihara, M. Kubota and H. Yamamoto, Synlett, 1996, 265-268.         [ Links ]

16 J. Izumi, I. Shiina and T. Mukaiyama, Chem. Lett, 1995, 141-145.         [ Links ]

17 R. Kumareswaran, A. Gupta and Y.D. Vankar, Synth. Commun., 1997, 27, 227-282.         [ Links ]

18 T. Okano, K. Miyamoto and K. Kiji, Chem. Lett., 1995, 246-249.         [ Links ]

19 J. Iqbal and R.R. Srivastava, J. Org. Chem., 1992, 57, 2001-2004.         [ Links ]

20 T. Mukaiyama, I. Shiina and M. Miyashita, Chem. Lett., 1992, 625-629.         [ Links ]

21 M. Miyashita, I. Shiina and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1993, 66, 1516-1518.         [ Links ]

22 H. Firouzabadi, N. Iranpoor, F. Nowrouzi and K. Amani, Chem. Commun., 2003, 764-769.         [ Links ]

23 N. Iranpoor, H. Firouzabadi and A. Jamalian, Tetrahedron Lett., 2005, 46, 7963-7966.         [ Links ]

24 H. Hagiwara, K. Morohashi, H. Sakai, T. Suzuki and M. Ando, Tetrahedron, 1998, 54, 5845-5852.         [ Links ]

25 M. Habibi, S. Tangestaninejad, V Mirkhani and B. Yadollahi, Tetrahedron, 2001, 57, 8333-8337.         [ Links ]

26 R.N. Ram and N.K. Meher, Tetrahedron, 2002, 58, 2997-3001.         [ Links ]

27 F. Shirini, K. Marjani, H.T. Nahzomi and M.A. Zolfigol, Phosphorus,. Sulfur and Silicon, 2007, 182, 1245-1251.         [ Links ]

28 B. Das, M. Krishnaiah, P. Balasubramanyam, B. Veeranjaneyulu and D.N. Kumar, Tetrahedron Lett., 2008, 49, 2225-2227.         [ Links ]

29 H.J. Park and J.C. Lee, Bull. Korean Chem. Soc. 2008, 29, 856-858.         [ Links ]

30 H. Firouzabadi, N. Iranpoor and S. Farahi, J. Mol. Catal. A: Chem., 2008, 289, 61-68.         [ Links ]

31 P. Strazzolini, A. G. Giumanini and S. Cauci, Tetrahedron, 1990, 46, 1081-1118.         [ Links ]

32 P. Chandra, S. Hausmann and A. Metz, Pharm. Res. Commun., 1974, 6, 311-317.         [ Links ]

33 T.V. Pratap and S. Baskaran, Tetrahedron Lett, 2001, 42, 1983-1985.         [ Links ]

 

 

Received 24 April 2008
Revised 5 November 2008
Accepted 13 January 2009

 

 

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

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