Traceless, self-cleaving solid- and solution-phase parallel synthesis of 3,4,7-trisubstituted 3,4-dihydroquinoxalin-2-ones

Journal of Combinatorial Chemistry

Volumn 3, Issue 6, 2001, Pages 572-577

  Laborde, Edgardo ^a   Peterson, Brian T ^a   Robinson, Louise ^a  

^a Telik Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINO ACID RECEPTOR BLOCKING AGENT; ENZYME INHIBITOR; GABAERGIC RECEPTOR AFFECTING AGENT; QUINOXALINE DERIVATIVE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

AMINO ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; ENZYME INHIBITORS; EXCITATORY AMINO ACID ANTAGONISTS; GABA AGENTS; QUINOXALINES;

EID: 0035513449     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc010025+     Document Type: Article

References (20)

1. Netzi, A.; Ostrech, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472.
2. (a) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182.
3. (b) Pan, P.-C.; Sun, C.-M. Tetrahedron Lett. 1999, 6443-6446.
4. (c) Schwarz, M. K.; Tumelty, D.; Gallop, M. A. Tetrahedron Lett. 1998, 39, 8397-8400.
5. (d) Lee, J.; Gauthier, D.; Rivero, R. A. J. Org. Chem. 1999, 64, 3060-3064.
6. Sarges, R.; Lyga, J. W. J. Heterocycl. Chem. 1988, 25, 1475-1479.
7. Gazit, A.; App, H.; McMahon, G.; Chen, J.; Levitzki, A.; Bohmer, F. D. J. Med. Chem. 1996, 39, 2170-2177.
8. (a) TenBrink, R. E.; Im, W. B.; Sethy, V. H.; Tang, A. H.; Carter, D. B. J. Med. Chem. 1994, 37, 758-768.
9. (b) Jacobsen, E. J.; TenBrink, R. E.; Stelzer, L. S.; Belonga, K. L.; Carter, D. B.; Im, H. K.; Im, W. B.; Sethy, V. H.; Tang, A. H.; VonVoigtlander, P. F.; Petke, J. D. J. Med. Chem. 1996, 39, 158-175.
10. (c) Jacobsen, E. J.; Stelzer, L. S.; TenBrink, R. E.; Belonga, K. L.; Carter, D. B.; Im, H. K.; Im, W. B.; Sethy, V. H.; Tang, A. H.; VonVoigtlander, P. F.; Petke, J. D.; Zhong, W.-Z.; Mickelson, J. W. J. Med. Chem. 1999, 42, 1123-1144.
11. Ohmori, J.; Sasamata-Shimizu, M.; Okada, M.; Sakamoto, S. J. Med. Chem. 1997, 40, 2053-2063.
12. Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. J. Med. Chem. 1993, 36, 2335-2342.
13. (a) Lee, J.; Murray, W. V.; Rivero, R. A. J. Org. Chem. 1997, 62, 3874-3879.
14. (b) Morales, G. A.; Corbett, J. W.; DeGrado, W. F. J. Org. Chem. 1998, 63, 1172-1177.
15. (c) Zaragoza, F.; Stephensen, H. J. Org. Chem. 1999, 64, 2555-2557.
16. (d) Krchnak, V.; Szabo, L.; Vagner, J. Tetrahedron Lett. 2000, 41, 2835-2838.
17. NAR Reactions. In Solid-Phase Organic Synthesis; Burgess, K., Ed.; John Wiley & Sons: New York, 2000; pp 81-117.
18. The yield of amides 10 generated from resin-bound phenylalanine could be improved by repeating the amidation step one more time.
19. Similar results were obtained at 45 °C for 8 h.
20. A larger excess of base and/or alkyl halide combined with heat (e.g., 45 °C, 12 h) provided variable amounts of a bis-alkylated product, as determined by LC/MS.