Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2,5-dihydroisoxazoles and isoxazoles

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 3438-3449

  Okitsu, Takashi ^a   Sato, Kana ^a   Potewar, Taterao M ^a   Wada, Akimori ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS; DIHYDROISOXAZOLES; EFFICIENT METHOD; HYDROXYLAMINE DERIVATIVE; IODOCYCLIZATION; ISOXAZOLES; OXIDATIVE AROMATIZATION; VALDECOXIB;

AROMATIC HYDROCARBONS; REACTION KINETICS;

AMINES;

2,5 DIHYDROISOXAZOLE DERIVATIVE; 4 IODO 3 (1 NAPHTHYL)ISOXAZOLE; 4 IODO 3 (2 METHOXYLPHENYL)ISOXAZOLE; 4 IODO 3 (2 METHYLPHENYL)ISOXAZOLE; 4 IODO 3 (2 NITROPHENYL)ISOXAZOLE; 4 IODO 3 (2 THIENYL)ISOXAZOLE; 4 IODO 3 (3 METHOXYLPHENYL)ISOXAZOLE; 4 IODO 3 (3 NITROPHENYL)ISOXAZOLE; 4 IODO 3 (4 METHOXYLPHENYL)ISOXAZOLE; 4 IODO 3 (4 METHYLPHENYL)ISOXAZOLE; 4 IODO 3 (4 NITROPHENYL)ISOXAZOLE; 4 IODO 3 PHENYLISOXAZOLE; BENZYL 2,5 DIHYDRO 4 IODO 3 (1 CYCLOHEXENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (1 NAPHTHYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (2 METHOXYLPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (2 METHYLPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (2 NITROPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (2 THIENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (3 METHOXYLPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (3 NITROPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (4 METHOXYLPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (4 METHYLPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 (4 NITROPHENYL) 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 PHENYL 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 2,5 DIHYDRO 4 IODO 3 PHENYL 5 METHYL 2H ISOXAZOLE 2 CARBOXYLATE; BENZYL 3 BUTYL 2,5 DIHYDRO 4 IODO 2H ISOXAZOLE 2 CARBOXYLATE; HYDROXYLAMINE; ISOXAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALDECOXIB;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; CYCLIZATION; DRUG SYNTHESIS; IODOCYCLIZATION; OXIDATION;

CYCLIZATION; HYDROXYLAMINES; IODINE; ISOXAZOLES; OXIDATION-REDUCTION;

EID: 79955557175     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200407b     Document Type: Article

References (64)

1. For isoxazoles, see: Alsalameh, S.; Burian, M.; Mahr, G.; Woodcock, B. G.; Geisslinger, G. Aliment. Pharmacol. Ther. 2003, 17, 489-501
2. Niho, N.; Kitamura, T.; Takahashi, M.; Mutoh, M.; Sato, H.; Matsuura, M.; Sugimura, T.; Wakabayashi, K. Cancer Sci. 2006, 97, 1011-1014
3. Mangold, U.; Dax, C. I.; Saar, K.; Schwab, W.; Kirschbaum, B.; Müllner, S. Eur. J. Biochem. 1999, 266, 1184-1191
4. Rowley, M.; Broughton, H. B.; Collins, I.; Baker, R.; Emms, F.; Marwood, R.; Patel, S.; Ragan, C. I.; Freedman, S. B.; Leeson, P. D. J. Med. Chem. 1996, 39, 1943-1945
5. For dihydroisoxazoles, see: Pulkkinen, J. T.; Honkakoski, P.; Peräkylä, M.; Berczi, I.; Laatikainen, R. J. Med. Chem. 2008, 51, 3562-3571
6. Maksimovic-Ivanic, D.; Mijatovic, S.; Harhaji, L.; Miljkovic, D.; Dabideen, D.; Cheng, K. F.; Mangano, K.; Malaponte, G.; Al-Abed, Y.; Libra, M.; Garotta, G.; Nicoletti, F.; Stosic-Grujicic, S. Mol. Cancer Ther. 2008, 7, 510-520
7. Dallannoce, C.; Magrone, P.; Bazza, P.; Grazioso, G.; Rizzi, L.; Riganti, L.; Gotti, C.; Clementi, F.; Frydenvang, K.; De Amici, M. Chem. Biodiv. 2009, 6, 244-259
8. Conti, P.; di Ventimiglia, S. J.; Pinto, A.; Tamborini, L.; Menniti, F. S.; Lazzaro, J. T.; De Micheli, C. Chem. Biodiv. 2008, 5, 657-663
9. Hentschel, F.; Lindel, T. Synthesis 2010, 181-204 and references therein
10. For a review, see: Wakefield, B. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Shaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 11, pp 229-288.
11. Zhu, M.-K.; Zhao, J.-F.; Loh, T.-P. J. Am. Chem. Soc. 2010, 132, 6284-6285
12. Yu, X.; Du, B.; Wang, K.; Zhang, J. Org. Lett. 2010, 12, 1876-1879
13. Debleds, O.; Zotto, C. D.; Vrancken, E.; Campagne, J.-M.; Retailleau, P. Adv. Synth. Catal. 2009, 351, 1991-1998
14. Suga, H.; Adachi, Y.; Fujimoto, K.; Furihata, Y.; Tsuchida, T.; Kakehi, A.; Baba, T. J. Org. Chem. 2009, 74, 1099-1113
15. Cecchi, L.; De Sarlo, F.; Machetti, F. Chem. - Eur. J. 2008, 14, 7903-7912 and references therein
16. Yeom, H.-S.; Lee, E.-S.; Shin, D. Synlett 2007, 2292-2294
17. For reviews, see: French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354-362
18. Larock, R. C. Acetylene Chem. 2005, 51-99
19. Togo, H.; Iida, S. Synlett 2006, 2159-2175
20. Mphahlele, M. J. Molecules 2009, 14, 4814-4837
21. For selected papers on the iodocyclizations of alkynes, see: Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 4764-4766
22. Worlikar, S. A.; Kesharwani, T.; Yao, T.; Larock, R. C. J. Org. Chem. 2007, 72, 1347-1353
23. Halim, R. H.; Scammells, P. J.; Flynn, B. L. Org. Lett. 2008, 10, 1967-1970
24. Barluenga, J.; Palomas, D.; Rubio, E.; González, J. M. Org. Lett. 2007, 9, 2823-2826
25. Garud, D. R.; Koketsu, M. Org. Lett. 2008, 10, 3319-3322
26. Bi, H.-P.; Guo, L.-N.; Duan, X.-H.; Gou, F.-R.; Huang, S.-H.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2007, 9, 397-400
27. Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2006, 45, 3140-3143
28. Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292-10296
29. Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409
30. Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2006, 71, 62-69
31. Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432-1437
32. Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511-3517
33. Khan, Z. A.; Wirth, T. Org. Lett. 2009, 11, 229-231
34. Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 12230-12231
35. Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409
36. Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141-1147
37. Mehta, S.; Larock, R. C. J. Org. Chem. 2010, 75, 1652-1658
38. Verma, A. K.; Aggarwal, T.; Rustagi, V.; Larock, R. C. Chem. Commun. 2010, 46, 4064-4066
39. Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203-5205
40. Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643-9647
41. Waldo, J. P.; Mehta, S.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 658-663
42. Foot, O. F.; Knight, D. W.; Low, A. C. L.; Li, Y. Tetrahedron Lett. 2007, 48, 647-650
43. Okitsu, T.; Sato, K.; Wada, A. Org. Lett. 2010, 12, 3506-3509
44. Crone, B.; Kirsch, S. F.; Umland, K.-D. Angew. Chem., Int. Ed. 2010, 49, 4661-4664
45. Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A. Org. Lett. 2008, 10, 4967-4970
46. Okitsu, T.; Nakazawa, D.; Kobayashi, A.; Mizohata, M.; In, Y.; Ishida, T.; Wada, A. Synlett 2010, 203-206
47. Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Löwe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203-2206
48. Jackson, S. K.; Karadeolian, A.; Driega, A. B.; Kerr, M. A. J. Am. Chem. Soc. 2008, 130, 4196-4201
49. Homsi, F.; Robin, S.; Rousseau, G. Org. Synth. 2000, 77, 206-211
50. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49
51. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483
52. Heck, R. F. Org. React. 1982, 27, 345-390
53. Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel, B. S.; Seibert, K. J. Med. Chem. 2000, 43, 775-777
54. Crich, D.; Wu, B. Org. Lett. 2006, 8, 4879-4882
55. Kwong, F. Y.; Li, Y. M.; Lam, W. H.; Qiu, L.; Lee, H. W.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. - Eur. J. 2005, 11, 3872-3880
56. Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3404-3409
57. Zhang, W.; Luo, Z.; Chen, C. H.-T.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443-10450
58. Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J. J. Org. Chem. 1998, 63, 7472-7480
59. Moreau, E.; Fortin, S.; Desjardins, M.; Rousseau, J. L. C.; Petitclerc, É.; C.-Gaudreault, R. Bioorg. Med. Chem. 2005, 13, 6703-6712
60. Sudeshna, S.; Dipankar, S.; Piyali, D.; Rima, L.; Amitabha, S. Tetrahedron 2009, 65, 4367-4374
61. Franks, M. A.; Schrader, E. A.; Pietsch, E. C.; Pennella, D. R.; Torti, S. V.; Welker, M. E. Bioorg. Med. Chem. 2005, 13, 2221-2233
62. Doutheau, A.; Gorg, J.; Diab, J. Tetrahedron 1985, 41, 329-338
63. Tessier, P. E.; Nguyen, N.; Clay, M. D.; Fallis, A. G. Org. Lett. 2005, 7, 767-770
64. Tirpak, M. R.; Hollingsworth, C. A.; Wotiz, J. H. J. Org. Chem. 1960, 25, 687-690