Reagent-controlled oxidative aromatization in iodocyclization: Switchable access to dihydropyrazoles and pyrazoles

Organic Letters

Volumn 12, Issue 15, 2010, Pages 3506-3509

  Okitsu, Takashi ^a   Sato, Kana ^a   Wada, Akimori ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IODINE; PYRAZOLE DERIVATIVE;

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

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDICATORS AND REAGENTS; IODINE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRAZOLES;

EID: 77955166860     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101365x     Document Type: Article

References (54)

1. Seltzman, H. H. Drug Dev. Res. 2009, 70, 601-615
2. Bensen, W. G. Pain 2003, 515-521
3. Wasylyk, C.; Zheng, H.; Castell, C.; Debussche, L.; Multon, M.-C.; Wasylyk, B. Cancer Res. 2008, 68, 1275-1283
4. Millis, D. L.; Weigel, J. P.; Moyers, T.; Buonomo, F. C. Vet. Ther. 2002, 3, 453-464
5. Nair, V.; Biju, A. T.; Mohanan, K.; Suresh, E. Org. Lett. 2006, 8, 2213-2216
6. Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Angew. Chem., Int. Ed. 2007, 46, 2070-2073
7. Cui, S.-L.; Wang, J.; Wang, Y.-G. Org. Lett. 2008, 10, 13-16
8. Basavaiah, D.; Roy, S. Org. Lett. 2008, 10, 1819-1822
9. For reviews, see
10. French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354-362
11. Larock, R. C. Acetylene Chem. 2005, 51-99
12. Togo, H.; Iida, S. Synlett 2006, 2159-2175
13. Mphahlele, M. J. Molecules 2009, 14, 4814-4837
14. For selected papers on the iodocyclizations of alkynes, see
15. Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2007, 46, 4764-4766
16. Worlikar, S. A.; Kesharwani, T.; Yao, T.; Larock, R. C. J. Org. Chem. 2007, 72, 1347-1353
17. Halim, R. H.; Scammells, P. J.; Flynn, B. L. Org. Lett. 2008, 10, 1967-1970
18. Barluenga, J.; Palomas, D.; Rubio, E.; González, J. M. Org. Lett. 2007, 9, 2823-2826
19. Garud, D. R.; Koketsu, M. Org. Lett. 2008, 10, 3319-3322
20. 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
21. Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2006, 45, 3140-3143
22. Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292-10296
23. Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409
24. Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2006, 71, 62-69
25. Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432-1437
26. Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511-3517
27. Khan, Z. A.; Wirth, T. Org. Lett. 2009, 11, 229-231
28. Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 12230-12231
29. Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406-2409
30. Mehta, S.; Waldo, J. P.; Larock, R. C. J. Org. Chem. 2009, 74, 1141-1147
31. Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A. Org. Lett. 2008, 10, 4967-4970
32. Okitsu, T.; Nakazawa, D.; Kobayashi, A.; Mizohata, M.; In, Y.; Ishida, T.; Wada, A. Synlett 2010, 203-206
33. Transition metal-catalyzed cyclization of hydrazides, see
34. Yang, Q.; Jiang, X.; Ma, S. Chem.-Eur. J. 2007, 13, 9310-9316
35. Cheng, X.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 4581-4583
36. Shu, W.; Yang, Q.; Jia, G.; Ma, S. Tetrahedron 2008, 64, 11159-11166
37. Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935-939
38. Rabjone, N. Org. Synth. 1948, 28, 375-377
39. Homsi, F.; Robin, S.; Rousseau, G. Org. Synth. 2000, 77, 206-211
40. Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763-766
41. Likhar, P. R.; Subhas, M. S.; Roy, S.; Kantam, M. L.; Sridhar, B.; Seth, R. K.; Biswas, S. Org. Biomol. Chem. 2009, 7, 85-93
42. During the preparation of this manuscript, the first report of controlling the oxidative aromatization for carbocycles appeared
43. Crone, B.; Kirsch, S. F.; Umland, K.-D. Angew. Chem., Int. Ed. 2010, 49, 4661-4664
44. Stepwise iodocyclizations/aromatizations, see
45. Knight, D. W.; Redfern, A. L.; Gilmore, J. Chem. Commun. 1998, 2207-2208
46. Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans. 1 2002, 622-628
47. Knight, D. W.; Rost, H. C.; Sharland, C. M.; Singkhonrat, L. Tetrahedron Lett. 2007, 48, 7906-7910
48. Schumacher, R. F.; Rosário, A. R.; Souza, A. C. G.; Menezes, P. H.; Zeni, G. Org. Lett. 2010, 12, 1952-1955
49. Synthesis of 4-iodopyrazoles, see
50. Waldo, J. P.; Mehta, S.; Larock, R. C. J. Org. Chem. 2008, 73, 6666-6670
51. Felding, J.; Kristensen, J.; Bjerregaard, T.; Sander, L.; Vedsø, P.; Begtrup, M. J. Org. Chem. 1999, 64, 4196-4198
52. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483
53. Heck, R. F. Org. React. 1982, 27, 345-390
54. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49