Palladium-catalyzed cyclocarbonylation of o-lodoanilines with Imidoyl Chlorides to produce quinazolin-4(3H)-ones

Organic Letters

Volumn 10, Issue 5, 2008, Pages 829-832

  Zheng, Zhaoyan ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; CARBON MONOXIDE; CHLORINATED HYDROCARBON; IODINATED HYDROCARBON; PALLADIUM; QUINAZOLINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AMIDINES; CARBON MONOXIDE; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; HYDROCARBONS, CHLORINATED; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; QUINAZOLINONES; STEREOISOMERISM;

EID: 43549118221     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7029454     Document Type: Article

References (41)

1. (a) Jang, C. S.; Fu, F. Y.; Wang, C. Y.; Huang, K. C; Lu, G.; Thou, T. C. Science 1946, 103, 59.
2. (b) D'yakonor, A. L.; Telezhenetskaya, M. V. Chem. Nat. Comput. 1997, 33, 221.
3. (c) Michael, J. P. Nat. Prod. Rep. 2004, 21, 650.
4. (d) Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787.
5. (a) Jiang, J. B.; Hesson, D. P.; Dusak, B. A.; Dexter, D. L.; Kang, G. J.; Hamel, E. J. Med. Chem. 1990, 33, 1721.
6. (b) Cao, S. L.; Feng, Y. P.; Jiang, Y. Y.; Liu, S. Y.; Ding, G. Y.; Li, R. T. Bioorg. Med. Chem. Lett. 2005, 75, 1915.
7. Malamas, M. S.; Millen, J. J. Med. Chem. 1991, 34, 1492.
8. Lowe, J. A.; Archer, R. L.; Chapin, D. S.; Cheng, J. B.; Helweg, D.; Johnson, J. L.; Koe, B. K.; Lebel, L. A.; Moore, P. F.; Nielsen, J. A.; Russo, L. L.; Shirley, J. T. J. Med. Chem. 1991, 34, 624.
9. (a) Habib, O. M.; Moawad, E. B.; Girges, M. M.; El-Shafei, A. M. Boll. Chim. Farm. 1995,134, 503.
10. (b) Ibrahim, S. S.; Abdel-Halim, A. M.; Gabr, Y.; El-Edfawy, S.; Abdel-Rahman, R. J. Chem. Res., Synop. 1997, 154.
11. (a) Mannscherck, A.; Koller, H.; Stuhler, G.; Davis, M. A.; Traber, J. Eur. J. Med. Chem. 1984, 19, 381.
12. (b) Hori, M.; Iemura, R.; Hara, H.; Ozaki, A.; Sukamoto, T.; Ohtaka, H. Chem. Pharm. Bull. 1990, 38, 1286.
13. Kung, P. P.; Casper, M. D.; Cook, K. L.; Wilson-Lingard, L.; Risen, L. M.; Vickers, T. A.; Ranken, R.; Blyn, L. B.; Wyatt, R.; Cook, P. D.; Ecker, D. J. J. Med. Chem. 1999, 42, 4705.
14. Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H. Tetrahedron Lett. 1999, 40, 2175.
15. LeMahieu, R. A.; Carson, M.; Nason, W. C; Parrish, D. R.; Welton, A. F.; Baruth, H. W.; Yaremko, B. J. Med. Chem. 1983, 26, 420.
16. Fisnerova, L.; Brunova, B.; Kocfeldova, Z.; Tikalova, J.; Maturova, E.; Grimova, Collect. Czech. Chem. Commun. 1991, 56, 2373.
17. For a review: Connolly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153.
18. (a) Bogert, M. T.; Hand, W. F. J. Am. Chem. Soc. 1902, 24, 1031.
19. (b) Bogert, M. T.; Hand, W. F. J. Am. Chem. Soc. 1903, 25, 935.
20. (c) Stephen, H.; Wadge, G. J. Chem. Soc. 1956, 4420.
21. (d) Taylor, E. C; Knopf, R. I.; Borror, A. L. J. Am. Chem. Soc. 1960, 82, 3152.
22. (e) Bogentoft, C; Kronberg, L.; Danielessan, B. Acta Pharm. Suec. 1969, 6, 485.
23. (a) Ozaki, K.; Yamada, Y.; Oine, T.; Ishizuka, T.; Iwasawa, Y. J. Med. Chem. 1985, 28, 568.
24. (b) Segarra, V.; Crespo, M. I.; Pujol, F.; Belata, J.; Domenech, T.; Miralpix, M.; Palacios, J. M.; Castro, A. Bioorg. Med. Chem. Lett. 1998, 8, 505.
25. (c) Kotsuki, H.; Sakai, H.; Morimoto, H.; Suenaga, H. Synlett 1999, 1993.
26. Abdel-Jalil, R. J.; Volter, W.; Saeed, M. Tetrahedron Lett. 2004, 45, 3475.
27. (a) Feldman, J. R.; Wagner, E. C. J. Org. Chem. 1942, 7, 31.
28. (b) Yale, H. L. J. Heterocycl. Chem. 1977,14, 1357.
29. (c) Mhaske, S. B.; Argade, N. R. J. Org. Chem. 2004, 69, 4563.
30. (a) Gouilleux. L.; Fehrentz, J. A.; Winternitz, F.; Martinez, J. Tetrahedron Lett. 1996, 37, 7031.
31. (b) Buckman, B. O.; Mohan, R. Tetrahedron Lett. 1996, 37. 4439.
32. Liu, J. F.; Lec, J.; Dalton, A. M.; Bi, G.; Yu, L.; Saldino, C. M.; McElory, E.; Brown, M. Tetrahedron Lett. 2005. 46, 1241.
33. (b) Montazeri, N.; Rad-Moghadam, K Phosphorus, Sulfur Silicon Relat. El em. 2004, 179. 2533.
34. Khosropour, A. R.; Mohammadpoor-Baltork, L; Ghorbankhami, H. Tetrahedron Lett. 2006, 47, 3561.
35. Akazome. M.; Yamamoto, J.; Kondo, T.; Watanabe, Y. 3. Organomet. Chem. 1995, 494. 229.
36. Murahashi, S.; Horiie, S. J. Am. Chem. Soc. 1956, 78. 4816.
37. Akazome. M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1993, 58, 310.
38. Shi. D. Q.; Rong. L. C; Wang, J. X.; Zhuang, Q. Y.; Wang. X. S; Hu. H. W. Synth. Commun. 2004, 34, 1759.
39. Larksarp, C; Alper, H. J. Org. Chem. 2000, 65, 2773.
40. Larksarp, C; Aipcr, H. Org. Lett. 1999, 1, 1619.
41. MaCrindlc, R.; Ferguson, G.; Arscnault, G. I; McAiccs, A. J.; Stephenson, D. K. J. Chem. Res., Synop. 1984, 360.