CuCl/DABCO/4-HO-TEMPO-catalyzed aerobic oxidative synthesis of 2-substituted quinazolines and 4 H -3,1-benzoxazines

Journal of Organic Chemistry

Volumn 77, Issue 2, 2012, Pages 1136-1142

  Han, Bing ^a   Yang, Xiu Long ^a   Wang, Chao ^a   Bai, Yong Wei ^a   Pan, Tai Chao ^a   Chen, Xin ^a   Yu, Wei ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2-AMINOBENZYL ALCOHOL; CATALYTIC SYSTEM; HETEROCYCLES; ONE-POT REACTION; QUINAZOLINES; TERMINAL OXIDANTS;

ALDEHYDES;

SYNTHESIS (CHEMICAL);

(E) 2 STYRYLQUINAZOLINE; 2 (2 CHLOROPHENYL)QUINAZOLINE; 2 (3 BROMOPHENYL)QUINAZOLINE; 2 (3 CHLOROPHENYL)QUINAZOLINE; 2 (4 CHLOROPHENYL)QUINAZOLINE; 2 (4 FLUOROPHENYL)QUINAZOLINE; 2 (4 METHOXYPHENYL)QUINAZOLINE; 2 (4 NITROPHENYL)QUINAZOLINE; 2 (FURAN 2 YL)QUINAZOLINE; 2 (PYRIDIN 3 YL)QUINAZOLINE; 2 4 TOLYLQUINAZOLINE; 2 AMINOBENZYLALCOHOL DERIVATIVE; 2 AMINOBENZYLAMINE DERIVATIVE; 2 PHENYLQUINAZOLIN; 2 PROPYLQUINAZOLINE; 2 SUBSTITUTED QUINAZOLINE DERIVATIVE; 2 TERT BUTYLQUINAZOLINE; 2,2,6,6 TETRAMETHYL 1 PIPERIDINYLOXY; 4H 3,1 BENZOXAZINE DERIVATIVE; 6 CHLORO 2 (4 CHLOROPHENYL)QUINAZOLINE; 6 CHLORO 2 (4 METHOXYPHENYL)QUINAZOLINE; ALDEHYDE; BENZOXAZINE DERIVATIVE; COPPER CHLORIDE; LIGAND; N LIGAND; OXYGEN; QUINAZOLINE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AEROBIC METABOLISM; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS;

ALDEHYDES; BENZOXAZINES; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; COPPER; MOLECULAR STRUCTURE; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; PIPERAZINES; QUINAZOLINES;

EID: 84862907528     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2020399     Document Type: Article

References (46)

1. Foster, B. A.; Coffrey, H. A.; Morin, M. J.; Rastinejad, F. Science 1999, 286, 2507
2. Gundla, R.; Kazemi, R.; Sanam, R.; Muttineni, R.; Sarma, J. A. R. P.; Dayam, R.; Neamati, N. J. Med. Chem. 2008, 51, 3367
3. Lüth, A.; Löwe, W. Eur. J. Med. Chem. 2008, 43, 1478
4. Lewerenz, A.; Hentschel, S.; Vissiennon, Z.; Michael, S.; Nieber, K. Drug Dev. Res. 2003, 58, 420
5. Doyle, L. A.; Ross, D. D. Oncogene 2003, 22, 7340
6. Dias, N.; Goossens, J. F.; Baldeyrou, B.; Lansiaux, A.; Colson, P.; Salvo, A. D.; Bernal, J.; Turnbull, A.; Mincher, D. J.; Bailly, C. Bioconjugate Chem. 2005, 16, 949
7. Hays, S. J.; Caprathe, B. W.; Gilmore, J. L.; Amin, N.; Emmerling, M. R.; Michael, W.; Nadimpalli, R.; Nath, R.; Raser, K. J.; Stafford, D.; Watson, D.; Wang, K.; Jaen, J. C. J. Med. Chem. 1998, 41, 1060
8. Sugiyama, H.; Hosoda, K.; Kumagai, Y.; Takeuchi, M.; Okada, M, U.S. Patent 4.596.801, 1986.
9. Mendes da Silva, J. F.; Walters, M.; Al-Damluji, S.; Ganellin, C. R. Bioorg. Med. Chem. 2008, 16, 7254
10. Burris, H. A., III. Oncologist 2004, 9, 10
11. Girard, C.; Liu, S.; Cadepond, F.; Adams, D.; Lacroix, C.; Verleye, M.; Gillardin, J.-M.; Baulieu, E.-E.; Schumacher, M.; Schweizer-Groyer, G. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 20505
12. Kopelman, P.; Bryson, A.; Hickling, R.; Rissanen, A.; Rossner, S.; Toubro, S.; Valensi, P. Int. J. Obes. 2007, 31, 494
13. Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. Chem. Commun. 2008, 44, 2935
14. Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. J. Org. Chem. 2009, 74, 4934
15. Wang, C.; Li, S.; Liu, H.; Jiang, Y.; Fu, H. J.Org. Chem. 2010, 75, 7936
16. Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841
17. Vanden Eynde, J. J.; Godin, J.; Mayence, A.; Maquestiau, A.; Anders, E. Synthesis 1993, 867
18. Peng, Y.; Zeng, Y.; Qiu, G.; Cai, L.; Pike, V. W. J. Heterocycl. Chem. 2010, 47, 1240
19. Maheswari, C. U.; Kumar, G. S.; Venkateshwar, M.; Kumar, R. A.; Kantam, M. L.; Reddy, K. R. Adv. Synth. Catal. 2010, 352, 341
20. Mase, N.; Mizumori, T.; Tatemoto, Y. Chem. Commun. 2011, 47, 2086
21. Cheng, L.; Wang, J.; Wang, M.; Wu, Z. Inorg. Chem. 2010, 49, 9392
22. Kumpulainen, E. T. T.; Koskinen, A. M. P. Chem.-Eur. J. 2009, 15, 10901
23. Figiel, P. J.; Sibaouih, A.; Ahmad, J. U.; Nieger, M.; Raisanen, M. T.; Leskela, M.; Repo, T. Adv. Synth. Catal. 2009, 351, 2625
24. Gassama, A.; Hoffmann, N. Adv. Synth. Catal. 2008, 350, 35
25. Jiang, N.; Ragauskas, A. J. ChemSusChem 2008, 1, 823
26. Mannam, S.; Alamsetti, S. K.; Sekar, G. Adv. Synth. Catal. 2007, 349, 2253
27. Figiel, P. J.; Leskela, M.; Repo, T. Adv. Synth. Catal. 2007, 349, 1173
28. Jiang, N.; Ragauskas, A. J. J. Org. Chem. 2006, 71, 7087
29. Jiang, N.; Ragauskas, A. J. Org. Lett. 2005, 7, 3689
30. Gamez, P.; Arends, I. W. C. E.; Sheldon, R. A.; Reedijk, J. Adv. Synth. Catal. 2004, 346, 805
31. Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Org. Biomol. Chem. 2003, 1, 3232
32. Gamez, P.; Arends, I. W. C. E.; Reedijk, J.; Sheldon, R. A. Chem. Commun. 2003, 2414
33. Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901
34. Sheldon, R. A.; Arends, I. W. C. E.; Ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774
35. Sheldon, R. A.; Arends, I. W. C. E. Adv. Synth. Catal. 2004, 346, 1051
36. Galli, C.; Gentili, P.; Lanzalunga, O. Angew. Chem., Int. Ed. 2008, 47, 4790
37. Vogler, T.; Studer, A. Synthesis 2008, 1979
38. Piera, J.; Backvall, Jan-E. Angew. Chem., Int. Ed. 2008, 47, 3506
39. Tebben, L.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 5034
40. Han, B.; Han, R.-F.; Ren, Y.-W.; Duan, X.-Y.; Xu, Y.-C.; Zhang, W. Tetrahedron 2011, 67, 5615
41. Han, B.; Liu, Q.; Liu, Z.; Mu, R.; Zhang, W.; Liu, Z.; Yu, W. Synlett 2005, 2333
42. Han, B.; Liu, Z.; Liu, Q.; Yang, L.; Liu, Z.; Yu, W. Tetrahedron 2006, 62, 2492
43. Chen, Y.; Qian, L.; Zhang, W.; Han, B. Angew. Chem., Int. Ed. 2008, 47, 9330
44. Han, B.; Wang, C.; Han, R.-F.; Yu, W.; Duan, X.-Y.; Fang, R.; Yang, X.-L. Chem. Commun. 2011, 47, 7818
45. Fritz-Langhals, E. Org. Process Res. Dev. 2005, 9, 577
46. Caneschi, A.; Grand, A.; Laugier, J.; Rey, P.; Subra, R. J. Am. Chem. Soc. 1988, 110, 2307