Synthesis of 6-amino-3,4-dihydroisoquinolinium derivatives by ring-opening reactions of acridizinium ions

Organic Letters

Volumn 10, Issue 5, 2008, Pages 757-760

  Deiseroth, Hans Jrög ^a   Granzhan, Anton ^a   Ihmels, Heiko ^a   Schlosser, Marc ^a   Tian, Maoqun ^a  

^a UNIVERSITY OF SIEGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; AMINE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SPECTROFLUOROMETRY; STEREOISOMERISM; SYNTHESIS;

ACRIDINES; AMINES; MOLECULAR STRUCTURE; QUINOLINIUM COMPOUNDS; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 43549102709     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702792r     Document Type: Article

References (37)

1. (a) Bringmann G. In Drugs against parasitic diseases: R&D methodologies and issues; Fairlamb, A. H., Ridley, R. G., Vial, H. J., Eds.; World Health Organisation: Geneva, 2003; p 145.
2. (b) Bentley, K. W. The Isoquinoline Alkaloids; Hardwood Academic: Amsterdam, 1998; Vol. 1.
3. Alvarez, M.; Joule, J. A. In Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom; Black, D., Ed.; Science of Synthesis, Vol. 15; Georg Thieme Verlag: Stuttgart, 2004; p 661.
4. (a) Ponte-Sucre, A.; Faber, J. H.; Gulder, T.; Kajahn, I.; Pedersen, S. E. H.; Schultheis, M.; Bringmann, G.; Moll, H. Antimicrob. Agents Chemother. 2007, 57, 188.
5. (b) Nishiyama, Y.; Moriyasu, M.; Ichimaru, M.; Iwasa, K.; Kato, A.; Mathenge, S. G.; Mutiso, P. B. C; Juma, F. D. Phytochemistry 2004, 65, 939.
6. (c) Kim, H.-J.; Park, J. E.; Jin, S.; Kim, J.-H.; Song, K. Chem. Biol. 2006, 13, 881.
7. (d) Kim, J.; Lee, S.; Choi, J.; Paik, Y.; Lee, Y.; Joo, H. PCT Int. Appl. WO 2006129978, 2006.
8. For recent examples: (a) Fejes, I.; Tõke, L.; Nyerges, M.;,Pak, C. S. Tetrahedron 2000, 56, 639.
9. (b) Fejes, I.; Nyerges, M.; Szöllõsy, A.; Blaskó, G.; Tõke, L. Tetrahedron 2001, 57, 1129.
10. (c) Nyerges, M.; Somfai, B.; Tóth, J.; Tõke, L.; Danscó, A.; Blaskó, G. Synthesis 2005, 2039.
11. (a) Taylor, S. J.; Taylor, A. M.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 1681.
12. (b) Taylor, A. M.; Schreiber, S. L. Org. Lett. 2006, 8, 143.
13. (a) Page, C. B. B.; Buckley, B. R.; Appleby, L. F.; Alsters, P. A. Synthesis 2005, 3405.
14. (b) Bohé, I,.; Kammoun, M. Tetrahedron Lett. 2004, 45, 747.
15. (c) Bohé. L.; Kammoun, M. Tetrahedron Lett. 2002, 43. 803.
16. (d) Page, P. C. B.; Rassias, G. A.; Barros. D.; Bethell, D.; Schilling. M. B. J. Chem. Soc. Perkin Trans. 1 2000, 3325.
17. (d) Page, P. C. B.; Rassias, G. A.; Baixos, D.; Ardakani, A.; Buckley, B.; Bethell. D.; Smith, T. A. D.; Slawin, A. M. Z. ,J. Org. Chem. 2001, 6926.
18. (e) Lusinchi, X.; Banquet, G. Tetrahedron 1997, 53, 13727.
19. (a) Granzhan, A.; Ihmels, H. Org. Lett. 2005, 7, 5119.
20. (b) Granzhan, A.; Ihmels, H. Arkivoc 2007, viii, 136.
21. Venn, S. V.; Tosunyan, D. E.; Zakharov, P. I.; Shevtsov. V. K.; Kuznctsov, E. V. Chem. Heterocycl. Compd. 1990, 26, 980.
22. (a) Rowland, G. B.; Rowland, E. B.; Zhang. Q.; Antilla, J. C. Curr. Org. Chem. 2006,10. 981.
23. (b) Buonora, P.; Olsen. J.-C; Oh, T. Tetrahedron 2001, 57. 6099.
24. (c) Tietze. I,. F.; Kettschau, G. Top. Curr. Chem. 1997, 189. 1.
25. (a) Bradsher C. K. In Comprehensive Heterocyclic Chemistry; Boultier A. I, McKillop, A., Eds.; Oxford: Pergamon Press, 1985; Vol. 2, p 525.
26. (b) Bradsher, C. K.; Sherer, J. P. J. Org. Chem. 1967, 32, 733.
27. (c) Krapcho, A. P.; Cadanmro, S. A.; Macnee, L. Arkivoc 2007, ix, 28.
28. With ethanal as aldehyde, the reaction did not take place, presumably because the intermediate enolate interferes with the reaction.
29. (a) Kim, S.-H., Ed, Functional Dyes; Elsevier, Amsterdam, 2006.
30. (b) Zollinger, H. Color Chemistry. 3rd ed.; VCH: Weinheim, Germany, 2003.
31. (b) Mishra, A.; Behera, R. L: Behera, P. K.; Mishra, B. K.; Behera, G. B. Chem. lieu. 2000, 100, 1973.
32. (a) Bogza, S. L.; Suikov, S. Y.; Bogdan, N. M.; Nikolyukin, Y. A.; Dulcnko, V. I. Chem. Heterocycl. Compel. 2004, 40, 1421.
33. (b) Bogza, S. L.; Nikolyukin, Y. A.; Zubritsky, M. Y.; Dulenko, V. I. Chem. Heterocycl. Compd 1995, 31, 272.
34. Van den Berg, O.; Jager, W. F.; Picken, S. J. J. Org. Chem. 2006, 71, 2666.
35. Granzhan, A.; Ihmcls, H.; Viola, G. J. Am. Chem. Soc. 2007, 129, 1254.
36. 2, as compared to yields in the other solvents, is also observed in the case of related cationic fluorophores and is presumably due to a high polarizability of this solvent; cf. refs 14 and 15.
37. Jones. G.; Jackson. W. R.; Choi. C. Y.; Bergmark, W. R. J. Phys. Chem. 1985, 89. 294.