Synthesis of novel 3-substituted pyrrolo[2,3-b]quinoxalines via an intramolecular heck reaction on an aminoquinoxaline scaffold

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8425-8427

  Li, Jie Jack ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLAMINE DERIVATIVE; BENZYLAMINE DERIVATIVE; METHYLAMINE; PALLADIUM COMPLEX; PYRROLE DERIVATIVE; QUINOXALINE DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0000587486     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9910839     Document Type: Article

References (39)

1. (a) David, R. Exp. Opin. Invest. Drug 1998, 7 (7), 1063-86.
2. (b) Harmenberg, J.; Akesson-Johansson, A.; Gräslund, A.; Malmfors, T.; Bergman, J.; Wahren, B.; Akerfeldt, S.; Lundblad, L.; Cox, S. Antiviral Res. 1991, 15, 193-204.
3. Naylor, M. A.; Stephen, M. A.; Nolan, J.; Sutton, B.; Tocher, J. H.; Fielden, E. M.; Adams, G. E.; Strafford, I. J. Anticancer Drug Des. 1993, 8, 439-61.
4. (a) Kim, K. S.; Qian, L.; Dickinson, K. E. J.; Delaney, C. L.; Bird, J. E.; Waldron, T. L.; Moreland, S. Biorg. Med. Chem. Lett. 1993, 3 (12), 2667-70.
5. (b) Dinsmore, A.; Garner, C. D.; Joule, J. A. Tetrahedron 1998, 54, 3291-302.
6. Li, J. J.; Yue, W. S. Tetrahedron Lett. 1999, 40 (24), 4507-10.
7. (a) Selby, T. P.; Denes, R.; Kilama, J. J.; Smith, B. K. Synthesis and Chemistry of Agrochemicals IV; ACS Symp. Ser. 584; 1995; pp 171-85.
8. (b) Auberson, Y. P.; Bischoff, S.; Moretti, R.; Schmutz, M.; Veenstra, S. J. Biorg. Med. Chem. Lett. 1998, 8, 65-70.
9. Tsubata, Y.; Suzuki, T.; Miyashi, T.; Yamashita, Y. J. Org. Chem. 1992, 57, 6749-55.
10. (a) Ames, D. E.; Brohi, M. I. J. Chem. Soc., Perkin Trans. 1 1980, 7, 1384-9.
11. (b) Ames, D. E.; Bull, D.; Takundwa, C. C. Synthesis 1981, 364-5.
12. Ames, D. E.; Mitchell, J. C.; Takundwa, C. C. J. Chem. Res., Synop. 1985, 5, 144-5.
13. Ames, D. E.; Mitchell, J. C.; Takundwa, C. C. J. Chem. Res., Miniprint 1985, 5, 1683-96.
14. Pyrrole annulation onto a benzene ring to prepare an indole via an intramolecular Heck reaction: (a) Mon, M.; Chiba, K.; Ban, Y. Tetrahedron Lett. 1977, 18, 1037-40.
15. (b) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709-10.
16. Patel, V. F.; Pattenden, G.; Rissell, J. J. Tetrahedron Lett. 1986, 27 (20), 2303-6.
17. Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291-4.
18. (e) Sundberg, R. J.; Pitts, W. J. J. Org. Chem. 1991, 56, 3048-54.
19. (f) Chen, L. C. Synthesis 1995, 385.
20. (g) Macor, J. E.; Ogilvie, R. J.; Wythes, M. J. Tetrahedron Lett. 1996, 37 (25), 4289-92.
21. (h) Yun, W.; Mohan, R. Tetrahedron Lett. 1996, 37 (25), 7189-92. Pyrrole annulation onto a quinoline ring via an intramolecular Heck reaction:
22. Comins, D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59 (9), 5120-1.
23. For reviews on intramolecular Heck reactions, see: (j) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 1998; pp 231-69.
24. (k) Link, J. T.; Overman, L. E. CHEMTECH 1998, 28 (8), 19-26.
25. Brase, S.; De Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 1998; pp 99-166.
26. Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53 (22), 7371-95.
27. (n) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3 (6), 447-71.
28. (o) Jeffery, T. Adv. Met.-Org. Chem. 1996, 5, 153-260.
29. (a) Dahl, O.; Nielsen, P. H. Acta Chem. Scand. 1967, 21 (5), 1153-61.
30. (b) Perlepes, S. P.; Garoufis, A.; Sletten, J.; Bakalbassis, E. G.; Plakatouras, G.; Katsarou, E.; Hadjiliadis, N. Inorg. Chim. Acta 1997, 261 (1), 93-102.
31. (a) Jeffery, T. Synthesis, 1987, 70-1.
32. (b) Jeffery, T. Tetrahedron Lett. 1994, 35 (24), 4103-6.
33. Jeffery, T. Tetrahedron 1996, 52 (30), 10113-30.
34. Jeffery, T. Tetrahedron Lett. 1998, 39 (32), 5751-4.
35. Newcomb, M.; Kumar, M. U. Tetrahedron Lett. 1990, 31, 1675-8.
36. (a) Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 4 (2), 679-80. For a review, see:
37. (b) Mitsunobu, O. Synthesis 1981, 1-28.
38. Gensler, W. J.; Rockett, J. C. J. Am. Chem. Soc. 1955, 77, 3262-4.
39. NAr reaction was predominant, giving rise exclusively to the corresponding chloroquinoxalines.