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South African Journal of Chemistry

versão On-line ISSN 1996-840X
versão impressa ISSN 0379-4350

S.Afr.j.chem. (Online) vol.63  Durban  2010

 

RESEARCH ARTICLE

 

Synthesis of (S)-3-aminoethyl-1,2,3,4-tetrahydroisoquinoline (TIQ-diamine) via the Mitsunobu protocol*

 

 

Rahul B. KawthekarI; Byron K. PetersI; Thavendran GovenderII, **; Hendrik G. KrugerI; Glenn E.M. MaguireI

ISchool of Chemistry, University of KwaZulu-Natal, Durban, South Africa
IISchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, 4000 South Africa
IIISchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, 4000 South Africa

 

 


ABSTRACT

The synthesis of (S)-3-Aminoethyl-1,2,3,4-tetrahydroisoquinoline (TIQ-diamine) was successfully achieved via the Mitsunobu protocol. The method from earlier reports utilizing aminolysis of commercially available TIQ-amino methyl ester, and reduction of the amide, proved to be inadequate for preparation of TIQ-diamines. The modified route requires three additional steps and consequently rendered three novel intermediates, which were furnished under mild conditions.

Keywords: Tetrahydroisoquinoline, TIQ-diamine, Mitsunobu reaction


 

 

Full text available only in PDF format.

 

Acknowledgements

This work was supported by National Research Foundation (South Africa, GUN 2073251), SA/Swedish Research Links Programme grant and Aspen Pharmacare, SA.

 

References

1 E.R. Parmee, L.L. Brockunier, J.F. He, S.B. Singh, M.R Candelore, M.A Cascieri, L.P. Deng, Y. Liu, L. Tota, M.J. Wyvratt, M.H. Fisher and A.E. Weber, Bioorg. Med. Chem. Lett. 2000, 10, 2283.         [ Links ]

2 M. Labarre, J. Butterworth, S. St-Onge, K. Payza, H. Schmidhammer, S. Salvadori, G. Balboni, R. Guerrini, S.D. Bryant and L.H. Lazarus, Eur. J. Pharmacol. 2000, 406, R1.         [ Links ]

3 M.J. Mokrosz, B. Duszynska, A. Wesolowska, J. Borycz, E. Chojnacka-Wojcik and J. Karolak-Wojciechowska, Med. Chem. Res. 10, 2000, 58.         [ Links ]

4 J. Dimaio and W. Wang, (Astra AB, Swed.). Sweden, European Patent (patno: EP914332), 1997, 76 pp.         [ Links ]

5 U.D. Spohr, M.J. Malone and N.B. Mantlo, (Amgen Inc., USA). USA patent (patno: US6096753), 2000, 92 pp.         [ Links ]

6 G.L. Grunewald, D.J. Sall andJ.A. Monn,J. Med. Chem. 1988, 31, 824.         [ Links ]

7 A.N. Hetenyi,T.A. Martinek, L. Lazar, Z. Zalan and F. Fulop, J. Org. Chem. 2003, 68, 5705.         [ Links ]

8 O. Mitsunobu, Synthesis-Stuttgart 1981, 1.         [ Links ]

9 O. Mitsunobu and M. Yamada, Bull. Chem. Soc. Japan 1967, 40, 2380.         [ Links ]

10 K.C.K. Swamy, N.N.B. Kumar, E. Balaraman and K. Kumar, Chem. Rev. 2009, 109, 2551.         [ Links ]

11 M.A. Walker, J. Org. Chem. 1995, 60, 5352.         [ Links ]

12 C. Simon, S. Hosztafi and S. Makleit, Tetrahedron 1994, 50, 9757.         [ Links ]

13 V Bardot, D. Gardette, Y. Gelas-Mialhe, J.C. Gramain and R. Remuson, Heterocycles 1998, 48, 507.         [ Links ]

14 F.J.Urban and R. Breitenbach, Synth Comm. 1999, 29, 645.         [ Links ]

15 K.K. Kothakonda and D.S. Bose, Bioorg. Med. Chem. Lett. 2004, 14, 4371.         [ Links ]

16 E.J. Corey, S. Shibata and R.K. Bakshi, J. Org. Chem. 1988, 53, 2861.         [ Links ]

17 E.J. Corey and J.O. Link, J. Amer. Chem. Soc. 1992, 114, 1906.         [ Links ]

18 Y. Kawanami, S. Murao, T. Ohga and N. Kobayashi, Tetrahedron 2003, 59, 8411.         [ Links ]

19 B.S. Furniss, A.J. Hannaford, P.W.G. Smith andA.R. Tatchell, in Vogel's Textbook of Practical Organic Chemistry, 5th edn., Pearson, New York, 1989, p. 774.         [ Links ]

20 A. Trifonova, K.E. Kallstrom and P.G. Andersson,. Tetrahedron 2004, 60, 3393.         [ Links ]

21 C.B. van Otterlo, W.A.L. de Koning and J.P. Michael, Tetrahedron 2003, 59, 8337.         [ Links ]

 

 

Received 7 July 2010
Revised 23 July 2010
Accepted 10 September 2010

 

 

* This paper was submitted upon invitation to invited speakers (CdK) at the South African Chemical Institute’s 11th Frank Warren Conference, January 2010, in Pietermaritzburg, KwaZulu-Natal, South Africa.
** To whom correspondence should be addressed. E-mail: govenderthav@ukzn.ac.za

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