Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source

Journal of Organic Chemistry

Volumn 79, Issue 21, 2014, Pages 10410-10416

  Li, Wanfang ^a   Wu, Xiao Feng ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL RESINS; AMIDES; CARBON MONOXIDE; CATALYSIS;

BENZOXAZINONES; CARBONYLATION REACTIONS; HETEROCYCLES; ORGANIC LABORATORY; ORGANIC SYNTHESIS; PALLADIUM-CATALYZED; PARAFORMALDEHYDES;

CARBONYLATION;

AMIDE; BENZOXAZINONE DERIVATIVE; CARBON 13; CARBON MONOXIDE; CARBONYL DERIVATIVE; PALLADIUM; PARAFORMALDEHYDE; BENZOXAZINE DERIVATIVE; FORMALDEHYDE;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DEBROMINATION; LABORATORY; MASS SPECTROMETRY; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; CHEMISTRY;

AMIDES; BENZOXAZINES; CATALYSIS; FORMALDEHYDE; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84909994697     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5020118     Document Type: Article

References (67)

1. Sicker, D.; Schulz, M. In Studies of Natural Product Chemistry; Attaur, R., Ed.; Elsevier: Amsterdam, 2002; Vol. 27, Part H, pp 185-232.
2. Grover, G.; Kini, S. G. Eur. J. Med. Chem. 2006, 41, 256-262
3. Coppola, G. M. J. Heterocycl. Chem. 2000, 37, 1369-1388
4. El-Mekabaty, A. International Journal of Modern Organic Chemistry 2013, 2, 81-121
5. Mitsos, C. P.; Markopoulos, J.; Igglessi-Markopoulou, O. J. Heterocycl. Chem. 1999, 36, 881
6. Kumar, A.; Sharma, S.; Archana; Bajaj, K.; Sharma, S.; Panwar, H.; Singh, T.; Srivastava, V. K. Bioorg. Med. Chem. 2003, 11, 5293-5299
7. Madkour, H. M. F. Arkivoc 2004, 36-54
8. Habib, O. O.; Hassan, H.; El-Mekabaty, A. Med. Chem. Res. 2013, 22, 507-519
9. Pavlidis, V. H.; Perry, P. J. Synth. Commun. 1994, 24, 533-548
10. Kato, S.; Morie, T.; Ohno, K.; Yoshida, N.; Yoshida, T.; Naruto, S. Chem. Pharm. Bull. 1995, 43, 582-587
11. Gilmore, J. L.; Hays, S. J.; Caprathe, B. W.; Lee, C.; Emmerling, M. R.; Michael, W.; Jaen, J. C. Bioorg. Med. Chem. Lett. 1996, 6, 679-682
12. Shariat, M.; Abdollahi, S. Molecules 2004, 9, 705-712
13. Ge, Z.-Y.; Xu, Q.-M.; Fei, X.-D.; Tang, T.; Zhu, Y.-M.; Ji, S.-J. J. Org. Chem. 2013, 78, 4524-4529
14. Kurihara, M.; Yoda, N. Tetrahedron Lett. 1965, 2597-2606
15. Kurihara, M.; Yoda, N. Bull. Chem. Soc. Jpn. 1966, 39, 1942-1948
16. Papadopoulos, E. P. J. Heterocycl. Chem. 1984, 21, 1411
17. Jarvest, R. L.; Parratt, M. J.; Debouck, C. M.; Gorniak, J. G.; John Jennings, L.; Serafinowska, H. T.; Strickler, J. E. Bioorg. Med. Chem. Lett. 1996, 6, 2463-2466
18. Rabilloud, G.; Sillion, B. J. Heterocycl. Chem. 1980, 17, 1065-1068
19. Minami, T.; Ogata, M.; Hirao, I.; Tanaka, M.; Agawa, T. Synthesis 1982, 1982, 231-233
20. Balsubramaniyan, V.; Argade, N. P. Tetrahedron Lett. 1986, 27, 2487-2488
21. Khajavi, M. S.; Shariat, S. M. Heterocycles 2005, 65, 1159-1165
22. Brennfuehrer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114-4133
23. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Soc. Rev. 2011, 40, 4986-5009
24. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1-35
25. Larock, R. C.; Fellows, C. A. J. Org. Chem. 1980, 45, 363-365
26. Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1996, 997
27. Salvadori, J.; Balducci, E.; Zaza, S.; Petricci, E.; Taddei, M. J. Org. Chem. 2010, 75, 1841-1847
28. Wu, X.-F.; Schranck, J.; Neumann, H.; Beller, M. Chem.-Eur. J. 2011, 17, 12246-12249
29. Wu, X.-F.; Neumann, H.; Beller, M. Chem.-Eur. J. 2012, 18, 12599-12602
30. Morimoto, T.; Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580-5588
31. Wu, L.; Liu, Q.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 6310-6320
32. Friis, S. D.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133, 18114-18117
33. Hermange, P.; Gøgsig, T. M.; Lindhardt, A. T.; Taaning, R. H.; Skrydstrup, T. Org. Lett. 2011, 13, 2444-2447
34. Gøgsig, T. M.; Nielsen, D. U.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2012, 14, 2536-2539
35. Nielsen, D. U.; Neumann, K.; Taaning, R. H.; Lindhardt, A. T.; Modvig, A.; Skrydstrup, T. J. Org. Chem. 2012, 77, 6155-6165
36. Brancour, C.; Fukuyama, T.; Mukai, Y.; Skrydstrup, T.; Ryu, I. Org. Lett. 2013, 15, 2794-2797
37. Burhardt, M. N.; Taaning, R. H.; Skrydstrup, T. Org. Lett. 2013, 15, 948-951
38. Korsager, S.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. J. Org. Chem. 2013, 78, 6112-6120
39. Li, H.; Neumann, H.; Beller, M.; Wu, X.-F. Angew. Chem., Int. Ed. 2014, 53, 3183-3186
40. Wu, X.-F.; Sharif, M.; Shoaib, K.; Neumann, H.; Pews-Davtyan, A.; Langer, P.; Beller, M. Chem.-Eur. J. 2013, 19, 6230-6233
41. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Chem. Commun. 2005, 3295-3297
42. Morimoto, T.; Fujioka, M.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Organomet. Chem. 2007, 692, 625-634
43. Natte, K.; Dumrath, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 10090-10094
44. Persson, A.; Dargy, R.; Gillberg, P. G.; Halldin, C.; Litton, J. E.; Swahn, C. G.; Sedvall, G. J. Neurosci. Methods 1991, 36, 53-61
45. Schou, M.; Pike, V. W.; Sovago, J.; Gulyas, B.; Gallagher, P. T.; Dobson, D. R.; Walter, M. W.; Rudyk, H.; Farde, L.; Halldin, C. Bioorg. Med. Chem. 2007, 15, 616-625
46. Cai, L.; Liow, J.-S.; Zoghbi, S. S.; Cuevas, J.; Baetas, C.; Hong, J.; Shetty, H. U.; Seneca, N. M.; Brown, A. K.; Gladding, R.; Temme, S. S.; Herman, M. M.; Innis, R. B.; Pike, V. W. J. Med. Chem. 2008, 51, 148-158
47. Khdour, O.; Skibo, E. B. Org. Biomol. Chem. 2009, 7, 2140-2154
48. De Bruyne, S.; La Regina, G.; Staelens, S.; Wyffels, L.; Deleye, S.; Silvestri, R.; De Vos, F. Nucl. Med. Biol. 2010, 37, 459-467
49. Funke, U.; Vugts, D. J.; Janssen, B.; Spaans, A.; Kruijer, P. S.; Lammertsma, A. A.; Perk, L. R.; Windhorst, A. D. J. Labelled Compd. Radiopharm. 2013, 56, 120-129
50. Mason, N. S.; Mathis, C. A.; Klunk, W. E. J. Labelled Compd. Radiopharm. 2013, 56, 89-95
51. Zanotti-Fregonara, P.; Barth, V. N.; Liow, J.-S.; Zoghbi, S. S.; Clark, D. T.; Rhoads, E.; Siuda, E.; Heinz, B. A.; Nisenbaum, E.; Dressman, B.; Joshi, E.; Luffer-Atlas, D.; Fisher, M. J.; Masters, J. J.; Goebl, N.; Kuklish, S. L.; Morse, C.; Tauscher, J.; Pike, V. W.; Innis, R. B. Eur. J. Nucl. Med. Mol. Imaging 2013, 40, 245-253
52. Pyo, A.; Kim, S.; Kumar, M. R.; Byeun, A.; Eom, M. S.; Han, M. S.; Lee, S. Tetrahedron Lett. 2013, 54, 5207-5210
53. Benedí, C.; Bravo, F.; Uriz, P.; Fernández, E.; Claver, C.; Castillón, S. Tetrahedron Lett. 2003, 44, 6073-6077
54. Wender, P. A.; White, A. W. Tetrahedron 1983, 39, 3767-3776
55. Saha, P.; Ramana, T.; Purkait, N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719-8725
56. Heinicke, J.; Gupta, N.; Surana, A.; Peulecke, N.; Witt, B.; Steinhauser, K.; Bansal, R. K.; Jones, P. G. Tetrahedron 2001, 57, 9963-9972
57. Kyba, E. P.; Liu, S. T.; Chockalingam, K.; Reddy, B. R. J. Org. Chem. 1988, 53, 3513-3521
58. Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350-5364
59. Ilies, M. A.; Masereel, B.; Rolin, S.; Scozzafava, A.; Câmpeanu, G.; Cîmpeanu, V.; Supuran, C. T. Bioorg. Med. Chem. 2004, 12, 2717-2726
60. Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802-1808
61. Saal, W. v. d.; Martens, A.; Zilch, H.; Boehm, E. U.S. Patent 5135949A1, 1992
62. Chem. Abstr. 1992, 113, 152047.
63. Aluri, B. R.; Niaz, B.; Kindermann, M. K.; Jones, P. G.; Heinicke, J. Dalton Trans. 2011, 40, 211-224
64. Barbero, N.; Carril, M.; SanMartin, R.; Domínguez, E. Tetrahedron 2007, 63, 10425-10432
65. Larksarp, C.; Alper, H. Org. Lett. 1999, 1, 1619-1622
66. Arcus, C. L.; Marks, R. E. J. Chem. Soc. (Resumed) 1956, 1627-1633
67. Gütschow, M. J. Org. Chem. 1999, 64, 5109-5115