Radical Mediated C-H Functionalization of 3,6-Dichloropyridazine: Efficient Access to Novel Tetrahydropyridopyridazines

Organic Letters

Volumn 17, Issue 10, 2015, Pages 2362-2365

  Neubert, Timothy D ^a   Schmidt, Yvonne ^a   Conroy, Erica ^a   Stamos, Dean ^a  

^a VERTEX PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; PYRIDAZINE DERIVATIVE; PYRIDINE DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CYCLIZATION; FREE RADICALS; MOLECULAR STRUCTURE; PYRIDAZINES; PYRIDINES;

EID: 84929618160     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00861     Document Type: Article

References (30)

1. O'Hara, F.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2013, 135, 12122 - 12134
2. Duncton, M. A. J. Med. Chem. Commun. 2011, 2, 1135 - 1161
3. Wang, J.; Wang, S.; Yu, X. Q. Chem. Commun. 2012, 48, 11769 - 11771
4. Sawada, S.; Okajima, S.; Aiyama, R. Chem. Pharm. Bull. 1991, 39, 1446 - 1454
5. Sawada, S.; Nokata, K.; Furata, T.; Yokokura, T. Chem. Pharm. Bull. 1991, 39, 2574 - 2580
6. Sawada, S.; Matsuoko, S.; Nokata, K.; Nagata, H.; Furuta, T.; Yokokura, T. Chem. Pharm. Bull. 1991, 39, 3183 - 3188
7. Zhou, Q.; Ruffoni, A.; Gianatassio, R.; Fujiwara, Y.; Sella, E.; Shabat, D.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 3949 - 3952
8. Heinisch, G.; Waglechner, R. J. Heterocycl. Chem. 1984, 21, 1727 - 1731
9. Minisci, F.; Citterio, A.; Vismara, E.; Giordano, C. Tetrahedron 1985, 41, 4157 - 4170
10. Katz, R. B.; Mistry, J.; Mitchell, M. B. Synth. Commun. 1989, 19, 317 - 326
11. Correia, C. A.; Yang, L.; Li, C. Org. Lett. 2011, 13, 4581 - 4583
12. Sugimori, A.; Mori, S.; Maeda, K.; Nishijima, M. Chem. Lett. 1984, 769 - 772
13. Duncton, M. A. J.; Estiarte, M. A.; Kelly, J. J. Org. Chem. 2009, 74, 6354 - 6357
14. Du, W.; Kaskar, B.; Blumbergs, P.; Curran, D. P. Bioorg. Med. Chem. 2003, 11, 451 - 458
15. Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257 - 10274
16. Hassan, M.; Rostom, S. A. F.; Basaif, S. A.; Makki, M. S. T.; Khan, K. A. Arch. Pharm. Sci. Res. 2013, 36, 1354 - 1368
17. Gil-Longo, J.; Laguna, M.; Verde, I.; Castro, M.; Orallo, F.; Fontenla, J.; Calleja, J.; Ravina, E.; Teran, C. J. Pharm. Sci. 1993, 82, 286 - 290
18. Bongartz, J.; Stokbroekx, R.; Van der Aa, M.; Luyckx, M.; Willems, M.; Ceusters, M.; Meerpoel, L.; Smets, G.; Jansen, T.; Wouters, W. Bioorg. Med. Chem. Lett. 2002, 12, 589 - 591
19. Mirzoeva, S.; Sawkar, Anu; Zasadzki, M.; Guo, L.; Velentza, A. V.; Dunlap, V.; Bourguignon, J.; Ramstrom, H.; Haiech, J.; Van Eldik, L. J. J. Med. Chem. 2002, 45, 563 - 566
20. Asif, M. Curr. Med. Chem. 2012, 19, 2984 - 2991
21. Cowden, C. J. Org. Lett. 2003, 5, 4497 - 4499
22. Baran, P.; Zhou, Q.; Ruffoni, A.; Gianatassio, R. Angew. Chem., Int. Ed. 2013, 52, 3949 - 3952
23. Baran, P.; Fujiwara, Y.; Janice, A.; Dixon, J. A. Nature 2012, 492, 95 - 100
24. Sugimoto, T.; Murata, S.; Matsuura, S.; Pfleiderer, W. Tetrahedron Lett. 1986, 27, 4179 - 4180
25. Tripathi, A. K.; Mukherjee, D.; Koul, S.; Taneja, S. C. ARIVOC 2009, xiii, 241 - 251
26. Rossi, B.; Pastori, N.; Clerici, A.; Punta, C. Tetrahedron 2012, 68, 10151 - 10156
27. Ghilardi, A.; Pastori, N.; Clerici, A.; Punta, C.; Porta, O. Org. Lett. 2008, 10, 5063 - 5066
28. Minisci, F.; Vismara, E.; Fontana, F.; Morini, G. J. Org. Chem. 1986, 51, 4411 - 4416
29. MacMillan, D. W. C.; Jin, J. Angew. Chem., Int. Ed. 2014, 53, 1 - 6
30. Seitz, G.; L. Görge, L. Chim. Ztg. 1984, 108, 331 - 332