Multistep microwave-assisted divergent synthesis of indolo-fused pyrazino-/diazepinoquinoxalinones on PEG support

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2174-2177

  Lai, Jin Ji ^a   Salunke, Deepak B ^a   Sun, Chung Ming ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; INDOLE DERIVATIVE; MACROGOL DERIVATIVE; PYRAZINE DERIVATIVE; QUINOXALINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; SOLUBILITY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; INDOLES; MICROWAVES; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS; PYRAZINES; QUINOXALINES; SOLUBILITY; STEREOISOMERISM;

EID: 77952350796     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100436r     Document Type: Article

References (26)

1. Lipkus, A. H.; Yuan, Q.; Lucas, K. A.; Funk, S. A.; Bartelt, W. F., III; Schenck, R. J.; Trippe, A. J. J. Org. Chem. 2008, 73, 4443-4451
2. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930
3. Lawrence, R. N. Drug Discov. Today 2000, 5, 172-175
4. Zhu, J.; Bienayme, H., Ed. Multicomponent reactions; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005; 468 pp.
5. Schreiber, S. L. Science 2000, 87, 1964-1969
6. Lovering, F.; Bikker, J.; Humblet, C. J. Med. Chem. 2009, 52, 6752-6756
7. Li, X.; Yang, K.; Li, W.; Xu, W. Drugs Future 2006, 31, 979-989
8. Gupta, L.; Talwar, A.; Chauhan, P. M. S. Curr. Med. Chem. 2007, 14, 1789-1803
9. Ramajayam, R.; Giridhar, R.; Yadav, M. R. Mini Rev. Med. Chem. 2007, 7, 793-812
10. Dunlop, J.; Marquis, K. L.; Lim, H. K.; Leung, L.; Kao, J.; Cheesman, C.; Rosenzweig-Lipson, S. CNS Drug Rev. 2006, 12, 167-177
11. Dodd, R. H.; Ouannes, C.; Potier, M. C.; de Carvalho, L. P.; Rossier, J.; Potier, P. J. Med. Chem. 1987, 30, 1248-1254
12. Glamkowski, E. J.; Fortunato, J. M.; Ong, H. H.; Allen, R. C.; Wilker, J. C.; Geyer, H. M., III. J. Med. Chem. 1984, 27, 81-83
13. Yuan, Y.; Liu, G.; Li, L.; Wang, Z.; Wang, L. J. Comb. Chem. 2007, 9, 158-170
14. Zhang, L.; Liu, G.; Zhang, S. D.; Yang, H. Z.; Li, L.; Wu, X. H.; Yu, J.; Kou, B. B.; Xu, S.; Li, J.; Sun, G. C.; Ji, Y. F.; Cheng, G. F. J. Comb. Chem. 2004, 6, 431-436
15. Lin, M. J.; Sun, C. M J. Comb. Chem 2006, 8, 455-458
16. All the microwave-assisted polymer-supported reactions were performed in a CEM Discover Microwave in closed vessel system.
17. Lin, M. J.; Sun, C. M. Tetrahedron Lett. 2003, 44, 8739-8742
18. Chen, C. H.; Chang, C. M.; Chen, H. Y.; Lai, J. J.; Sun, C. M. J. Comb. Chem. 2007, 9, 618-626
19. We reported microwave-mediated Fmoc deprotection under open vessel conditions: Wu, C. Y.; Sun, C. M. Synlett 2002, 1709-1711
20. 1H NMR monitoring toward the formation of key intermediates 4 on a PEG support is included in the Supporting Information.
21. Aoki, K.; Obata, T.; Yamazaki, Y.; Mori, Y.; Hirokawa, H.; Koseki, J.; Hattori, T.; Niitsu, K.; Takeda, S.; Aburada, M.; Miyamoto, K. Chem. Pharm. Bull. 2007, 55, 255-267
22. Krchnák, V.; Szabo, L.; Vágner, J. Tetrahedron Lett. 2000, 41, 2835-2838
23. Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A J. Org. Chem. 2001, 66, 1403-1412
24. Krupkova, S.; Soural, M.; Hlavac, J.; Hradil, P. J. Comb. Chem. 2009, 11, 951-955
25. Zhang, L. H.; Meier, W.; Wats, E.; Costello, T. D.; Ma, P.; Ensinger, C. L.; Rodgers, J. M.; Jacobson, I. C.; Rajagopalan, P. Tetrahedron Lett. 1995, 36, 8387-8390
26. Zheng, L.; Xiang, J.; Dang, Q.; Guo, S.; Bai, X. J. Comb. Chem. 2005, 7, 813-815