SHORT COMMUNICTION

 

Synthesis of 9H-indeno [1, 2-b] pyrazine and 11H-indeno [1, 2-b] quinoxaline derivatives in one-step reaction from 2-bromo-4-chloro-1-indanone

 

 

S. Jasouri^{I, II}; J. Khalafy^{I, *}; M. Badali^II ; R.H. Prager^III

^IDepartment of Chemistry, Urmia University, Urmia 57154, Iran
^IIDaana Pharmaceutical Co., P.O. Box 5181, Tabriz 51575, Iran
^IIISchool of Chemical and Physical Sciences, Flinders University, G.P.O. Box 2100, Adelaide, Australia 5001

 

 

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ABSTRACT

The reaction of 2-bromo-4-chloro-1-indanone with 2,3-diaminomaleonitrile, benzene-1,2-diamine and 4-methylbenzene-1,2-diamine in glacial acetic acid gave 8-chloro-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile, 1-chloro-11H-indeno[1,2-b]quinoxa-line and 1-chloro-7-methyl-11H-indeno[1,2-b]quinoxaline, respectively, in good yield.

Keywords: 2-bromo-4-chloro-1-indanone, diaminopyridine, indeno[1,2-b]quinoxaline, indeno[1,2-b]pyrazine, debromination

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Full text available only in pdf format.

 

Acknowledgements

We gratefully acknowledge the University of Urmia and Daana Pharmaceutical Co. for providing a fellowship for the present work.

 

References

1 S. El-Hawash, N. Habib and M. Kassem, Pharm (Weinheim), 2006, 339, 564.         [ Links ]

2 S. Khan, K. Saleem and Z. Khan, Eur. J. Med. Chem, 2007, 42, 103.         [ Links ]

3 V. Tandon, D. Yadav, H. Maurya, A. Chaturvedi and P. Shukla, Bio. Org. Med. Chem., 2006, 14, 6120.         [ Links ]

4 H. Refaat, A. Moneer and O. Khalil, Arch Pharm Res, 2004, 27, 1093.         [ Links ]

5 A. Carta, M. Loriga, S. Zanetti and L. Sechi, Il Farmaco, 2003, 58, 1251.         [ Links ]

6 B. Zarranz, I. Aldana, A. Jaso and A. Monge, Bioorg. Med. Chem., 2004, 12, 3711.         [ Links ]

7 F. Grande, F. Aiello, O. Grazia, A. Brizzi, A. Garofalo and N. Neamati, Bio. Org. Med. Chem., 2007, 15, 288.         [ Links ]

8 J. Jung, E. Jung, K. Nam-Goong, J. Cho, H. Kim, S. Park, Y. Yoo, J. Kwon and H. Lee, Arch. Pharm. Res., 2006, 9, 276.         [ Links ]

9 H. Gali-Muhtasib, M. Diab-Assaf and M. Haddadin, Cancer Chemother. Pharmacol, 2005, 55, 369.         [ Links ]

10 C. Liu, B. Wang, W. Li, L. Yun, Y. Liu, R. Su, J. Li and H. Liu, Bioorg. Med. Chem., 2004, 12, 4701.         [ Links ]

11 M. Loriga, S. Piras, G. Paglietti, M. Costi and A. Venturelli, Il Farmaco, 2003, 58, 51.         [ Links ]

12 N. Vekariya, M. Khunt and A. Parikh. Ind. J. Chem, 2003, 42, 421.         [ Links ]

13 J. Azizian, A. Karimi, Z. Kazemizadeh, A. Mohammadi and M. Mohammadizadeh, Tetrahedron Letters, 2006, 46, 6155.         [ Links ]

14 M. Honari, M. Helliwell, M.M. Bradarani and J.A. Joule, ARKIVOK, 2008, xiv, 166.         [ Links ]

15 A. Al-Azmi, A. Zaher and A. Elassar, B.L. Booth, Tetrahedron, 2003, 59, 2749.         [ Links ]

16 T. Utsukihara, H. Nakamura, M. Watanabe and C.A. Horiuchi, Tetrahedron Letters, 2006, 47, 9359.         [ Links ]

17 Y. Kubota, T. Shibata, E. B. Horiguchi, J. Uehara, K. Funabiki, S. Matsumoto, M. Ebihara and M. Matsui, Tetrahedron, 2009, 65, 2506.         [ Links ]

18 A. Guirado, J. Sanchez, A. Cerezo, D. Bautista and J. Galvez, Tetrahedron, 2009, 65, 2254.         [ Links ]

19 S. Jasouri, J. Khalafi, M. Badali and M. Piltan, S. Afr. J. Chem, 2010, 63, 83-87.         [ Links ]

 

 

Received 22 January 2011
Revised 21 April 2011
Accepted 4 May 2011

 

 

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