A diversity oriented four-component approach to tetrahydro-β- carbolines initiated by Sonogashira coupling

Organic and Biomolecular Chemistry

Volumn 3, Issue 24, 2005, Pages 4382-4391

  Karpov, Alexei S ^a   Rominger, Frank ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CARBOLINES; STEREOCENTERS; X-RAY STRUCTURE ANALYSIS;

DERIVATIVES;

CARBOLINE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROGEN; QUINOLIZINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

AMINATION; AZA COMPOUNDS; CARBOLINES; HYDROGEN; MOLECULAR STRUCTURE; QUINOLIZINES;

EID: 29844458184     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b511861a     Document Type: Article

References (46)

1. For overviews, see e.g.: E. Breitmaiet in Alkaloids, Teubner Studienbücher, Stuttgart, 1997, p. 52;
2. K. Stuart-and R. Woo-Ming, Heterocydes, 1975, 3, 223;
3. B. T. Ho, W. M. McIsaac, K. E. Walker and V. Estevez, J. Pharm. Sci., 1968, 57, 269;
4. The Chemistry of Heterocyclic Compounds, Part IV Supplement of Vol. 25, ed., J. E. Saxton, Wiley, Chichester, 1994.
5. For reviews, see e.g.: S. Urban, S. J. H. Hickford, J. W. Blunt and M. H. G. Munro, Curr. Org. Chem., 2000, 4, 765;
6. J. B. Hudson, Antiviral Res., 1989, 12, 55;
7. D. J. McKenna and G. H. Towers, J. Psychoact. Drugs, 1984, 16, 347.
8. B. T. Ho, J. Pharm. Sci., 1972, 61, 821.
9. J. E. Audia, D. A. Evrard, G. R. Murdoch, J. J. Droste, J. S. Nissen, K. W. Schenk, P. Fludzinski, V. L. Lucaites, D. L. Nelson and M. L. Cohen, J. Med. Chem., 1996, 39, 2773;
10. B. E. Love and P. S. Raje, J. Org. Chem., 1994, 59, 3219 and references therein;
11. C. A. Busacca, M. C. Eriksson, Y. Dong, A. S. Prokopowicz, A. M. Salvagno and M. A. Tschantz, J. Org. Chem., 1999, 64, 4564 and references therein.
12. For recent reviews, see e.g.: L. Weber, K. Illgen and M. Almstetter, Synlett, 1999, 366;
13. I. Ugi, A. Dömling and B. Werner, J. Heterocycl. Chem., 2000, 37, 647.
14. S. Kobayashi, Chem. Soc. Rev., 1999, 28, 1.
15. For reviews, see e.g.: K. Sonogashira, in Metal-catalyzed Cross-coupling Reactions, eds., F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 5;
16. K. Sonogashira, J. Organomet. Chem., 2002, 653, 46;
17. R. R. Tykwinski, Angew. Chem., 2003, 115, 1604;
18. R. R. Tykwinski, Angew. Chem., Int. Ed., 2003, 42, 1566.
19. For recent examples, see: M. Eckhardt and G. C. Fu, J. Am. Chem. Soc., 2003, 125, 13642;
20. A. Soheili, J. Albaneze-Walker, J. A. Murry, P. G. Dormer and D. L. Hughes, Org. Lett., 2003, 5, 4191;
21. J. Cheng, Y. Sun, F. Wang, M. Guo, J. Xu, Y. Pan and Z. Zhang, J. Org. Chem., 2004, 69, 5428.
22. A. S. Karpov, F. Rominger and T. J. J. Müller, J. Org. Chem., 2003, 68, 1503.
23. For the first report on the cross-coupling reaction of acid chlorides and alkynes using only one equivalent of triethylamine, see: A. S. Karpov and T. J. J. Müller, Org. Lett., 2003, 5, 3451.
24. For syntheses of pyrazoles, see e.g. : C. Moureu and R. Delange, Bull. Soc. Chim. Fr., 1901, 25, 302;
25. R. D. Miller and O. Reiser, J. Heterocycl. Chem., 1993, 30, 755;
26. D. B. Grotjahn, S. Van, D. Combs, D. A. Lev, C. Schneider, M. Rideout, C. Meyer, G. Hernandez and L. Mejorado, J. Org. Chem., 2002, 67, 9200.
27. For syntheses of isoxazoles, see e.g.: K. Bowden and E. R. H. Jones, J. Chem. Soc., 1946, 25, 953;
28. R. M. Adlington, J. E. Baldwin, D. Catterick, G. J. Pritchard and L. T. Tang, J. Chem. Soc. Perkin Trans. 1, 2000, 303.
29. For syntheses of pyrimidines, see e.g. : R. M. Adlington, J. E. Baldwin, D. Catterick and G. J. Pritchard, Chem. Commun., 1997, 1757;
30. M. C. Bagley, D. D. Hughes, P. H. Taylor and X. Xiong, Synlett, 2003, 259;
31. M. C. Bagley, D. D. Hughes, H. M. Sabo, P. H. Taylor and X. Xiong, Synlett, 2003, 1443.
32. For syntheses of pyridines, see e.g. : F. Bohlmann and D. Rahtz, Chem. Ber., 1957, 90, 2265;
33. M. C. Bagley,C. Brace, J. W. Dale, M. Ohnesorge, N. G. Philips, X. Xiong and J. Bower, J. Chem. Soc., Perkin Trans. 1, 2002, 1663;
34. M. C. Bagley, J. W. Dale, M. Ohnesorge, N. G. Philips, X. Xiong and J. Bower, J. Comb. Chem., 2003, 5, 41.
35. A. S. Karpov and T. J. J. Müller, Synthesis, 2003, 2815.
36. Preliminary communication: A. S. Karpov, T. Oeser and T. J. J. Müller, Chem. Commun., 2004, 1502.
37. A. S. Karpov, E. Merkul, T. Oeser and T. J. J. Müller, Chem. Commun., 2005, 2581.
38. For recent examples of aza-annulations, see e.g. : P. Benovsky, G. A. Stephenson and J. R. Stille, J. Am. Chem. Soc., 1998, 120, 2493;
39. K. Paulvannan and T. Chen, J. Org. Chem., 2000, 65, 6160.
40. For a review, see eg.: E. D. Cox and J. M. Cook, Chem. Rev., 1995, 95, 1797.
41. The aza-annulation-Pictet-Spengler reaction was reported last year independently from our group: M. M. Abelman, J. K. Curtis and D. R. James, Tetrahedron Lett., 2003, 44, 6527.
42. For a recent review on cyclization of N-acyliminium ions, see e.g.: B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi and C. A. Maryanoff, Chem. Rev., 2004, 104, 1431.
43. For mechanistic implications on the aza-annulation reaction, see: N. S. Barta, A. Brode and J. R. Stille, J. Am. Chem. Soc., 1994, 116, 6201.
44. I. Fleming, in Pericyclic Reactions, Oxford University Press, New York, 2002, pp. 78 and 85.
45. Organikum, 14 edition, VEB Deutscher Verlag der Wissenschaften, Berlin, 1993.
46. G. M. Sheldrick, Bruker Analytical X-ray-Division, Madison, Wisconsin.