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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

 

RESEARCH ARTICLE

 

Selective bromination of 4-chloro-1-indanone and synthesis of (4-chloro-2, 3-dihydro-1H-indene-2-yl)methanamine

 

 

S. JasouriI, II; J. KhalafyI, *; M. BadaliII; M. PiltanI

IDepartment of Chemistry, Urmia University, Urmia 57154, Iran
IIDaana Pharmaceutical Co., P.O. Box 5181-51575, Tabriz, Iran

 

 


ABSTRACT

The synthesis of 4-chloro-1-indanone in four steps from 2-chlorobenzaldehyde was investigated. Bromination of this compound under various conditions occurred in the cyclopentanone ring, producing mono- and dibromo derivatives. Cyanation of 2-bromo-4-chloro-1-indanone followed by reduction gave (4-chloro-2, 3-dihydro-1H-indene-2-yl)methanamine in quantitative yield.

Keywords: Indanone, bromination, cyanation, reduction, GABAB receptors


 

 

Full text available only in PDF format.

 

Acknowledgements

We are grateful for financial support from Urmia University and Daana Pharmaceutical Co. and S.J. is grateful to Daana Pharmaceutical Co. for a Ph.D. scholarship.

 

References

1 L.F. Fieser and E.B. Hershberg J. Am. Chem. Soc., 1937, 59, 394-398.         [ Links ]

2 C. Berrier, J.C. Jacquesy and M.P. Jouannetaaud, Tetrahedron, 1984, 40, 4973-4979.         [ Links ]

3 R. Takeuchi and H.Yasue, J. Org. Chem., 1993, 58, 5386-5392.         [ Links ]

4 K. Lan and Z. Shan, Synth. Comm., 2007, 37, 2171-2177.         [ Links ]

5 D.M. Cui, C. Zhang, M. Kawamura and S. Shimada, Tetrahedron Letters, 2004, 45, 1741-1745.         [ Links ]

6 S. Nan'ya, T. Kitahara, K. Fujii, A.C.Bajji and Y. Butsugan, J. Heterocyclic Chem, 1992, 29, 1525-1528.         [ Links ]

7 Ullmanns Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.         [ Links ]

8 D. La, P.B.D. Mare and R. Bolton, Electrophilic Additions to Unsaturated Systems, Elsevier, Amsterdam, the Netherlands, 1982.         [ Links ]

9 T. Choi and E. Ma, Molecules., 2007, 12, 74-85.         [ Links ]

10 A. Podgorsek, S. Stavber, M. Zupan and J. Iskra, TetrahedronLett., 2006, 47, 7245-7247.         [ Links ]

11 A. Podgorsek, S. Stavber, M. Zupan and J. Iskra, Tetrahedron, 2009, 65, 4429-4439.         [ Links ]

12 I. Pravst, M. Zupan and S. Stavber, Tetrahedron Lett. 2006, 47, 4707-4710.         [ Links ]

13 J. Sam and T.C. Snapp, J. Pharm. Sci., 1965, 54, 756-760.         [ Links ]

14 A.L. Wilds, J. Am. Chem. Soc, 1942, 64, 1421-1429.         [ Links ]

15 W.S. Johnson, J.M. Anderson and W.E. Shelberg, J. Am. Chem. Soc., 1944, 66, 218-222.         [ Links ]

16 H.O. House andV. Paragamian, J. Am. Chem. Soc, 1959, 82, 1452-1457.         [ Links ]

17 N.S. Kus, Turk. J. Chem. 2009, 33, 479-486.         [ Links ]

18 Y. Kojima and S. Kawaguchi, Bull. Chem. Soc. Japan, 1972, 45, 1293-1299.         [ Links ]

19 A. Jordao, P. Afonso, V Ferreira, M.D. Souza, M. Almeida and A. Cunha, Eur. J. Med. Chem., 2009, 44, 3777-3781.         [ Links ]

20 D.I.B. Kerr and J. Ong Pharmacol. Therap., 1995, 67, 187-246.         [ Links ]

21 D.I.B.Kerr, and J. Ong Current Med .Chem. CNS Agents., 2001, 1, 27-42.         [ Links ]

22 J. Khalafy, R.H. Prager and N.M. Puspawati, Turk J. Chem, 2008, 32, 755-763.         [ Links ]

23 D.I.B. Kerr, J. Ong,M. Perkins, R.H. Prager and N.M. Puspawati, Aust. J. Chem., 2006, 59, 445-456.         [ Links ]

24 D.W James and M.Y. Kraig, J. Am. Chem. Soc. 1994, 116, 1831-1838.         [ Links ]

25 J. Ong, D.A.S. Parker, V. Marino, D.I.B. Kerr, N.M. Puspawati and R.H. Prager, Eur. J. Pharmacology, 2005, 507, 35-42.         [ Links ]

26 N.G. Bowery, Trends Pharmacol. Sci, 1989, 10, 401-407.         [ Links ]

 

 

Received 23 June 2010
Revised 10 July 2010
Accepted 12 July 2010

 

 

* To whom correspondence should be addressed. E-mail: j.khalafi@mail.urmia.ac.ir ; jkhalafi@yahoo.com

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