Browse > Article
http://dx.doi.org/10.5012/bkcs.2014.35.9.2635

Synthesis of 3,4,5-Trisubstituted Isoxazoles through Gold-Catalyzed Cascade Cyclization-Oxidative Alkynylation and Cyclization-Fluorination of 2-Alkynone O-Methyloximes  

Song, Doo-Hee (College of Pharmacy & Graduate School of Pharmaceutical Sciences, Global Top5 Research Program, Ewha Womans University)
Ryu, Jae-Sang (College of Pharmacy & Graduate School of Pharmaceutical Sciences, Global Top5 Research Program, Ewha Womans University)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.9, 2014 , pp. 2635-2644 More about this Journal
Abstract
Gold-catalyzed tandem cyclization-oxidative alkynylation and cyclization-fluorination reactions of 2-alkynone O-methyloximes are described. The reactions proceed smoothly at room temperature in the presence of 10 mol % of $(PPh_3)AuNTf_2$, 2.5 equivalents of selectfluor, and 2 equivalents of $K_3PO_4$. 2-Alkynone O-methyloximes undergo intramolecular oxyauration/cyclization and ensuing oxidative cross-coupling and fluorination process to afford the corresponding 3,4,5-trisubstituted isoxazoles in a cascade manner.
Keywords
Gold; Isoxazole; O-Methyloxime; Cross-coupling; Alkyne;
Citations & Related Records
연도 인용수 순위
  • Reference
1 (f) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.   DOI   ScienceOn
2 (g) Hoffmann-Roder, A.; Krause, N. Org. Biomol. Chem. 2005, 3, 387.   DOI   ScienceOn
3 (h) Jimenez-Nunez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.   DOI   ScienceOn
4 (i) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.   DOI   ScienceOn
5 (j) Skouta, R.; Li, C.-J. Tetrahedron 2008, 64, 4917.   DOI   ScienceOn
6 (k) Widenhoefer, R. A. Chem. Eur. J. 2008, 14, 5382.   DOI   ScienceOn
7 (a) Zhang, G.; Cui, L.; Wang, Y.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 1474.   DOI   ScienceOn
8 Pinho, E. M.; Teresa, M. V. D. Curr. Org. Chem. 2005, 9, 925.   DOI   ScienceOn
9 Daidone, G.; Raffa, D.; Maggio, B.; Plescia, F.; Cutuli, V. M. C.; Mangano, N. G.; Caruso, A. Arch. Pharm. 1999, 332, 50.   DOI
10 Cali, P.; Naerum, L.; Mukhija, S.; Hjelmencrantz, A. Bioorg. Med. Chem. Lett. 2004, 14, 5997.   DOI   ScienceOn
11 Liu, J.; Yu, L.-F.; Eaton, J. B.; Caldarone, B.; Cavino, K.; Ruiz, C.; Terry, M.; Fedolak, A.; Wang, D.; Ghavami, A.; Lowe, D. A.; Brunner, D.; Lukas, R. J.; Kozikowski, A. P. J. Med. Chem. 2011, 54, 7280.   DOI   ScienceOn
12 Bandiera, T.; Grunanger, P.; Albini, F. M. J. Heterocycl. Chem. 1992, 29, 1423.   DOI
13 Cuadrado, P.; Gonzalez-Nogal, A. M.; Valero, R. Tetrahedron 2002, 58, 4975.   DOI   ScienceOn
14 Heaney, F. Eur. J. Org. Chem. 2012, 3043.
15 Waldo, J. P.; Mehta, S.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 658.   DOI   ScienceOn
16 Moore, J. E.; Davies, M. W.; Goodenough, K. M.; Wybrow, R. A. J.; York, M.; Johnson, C. N.; Harrity, J. P. A. Tetrahedron 2005, 61, 6707.   DOI
17 Denmark, S. E.; Kallemeyn, J. M. J. Org. Chem. 2005, 70, 2839.   DOI   ScienceOn
18 Trost, B. M. Angew. Chem. Int. Ed. 1995, 34, 259.   DOI   ScienceOn
19 Clarke, P. A.; Santos, S.; Martin, W. H. C. Green Chem. 2007, 9, 438.   DOI   ScienceOn
20 Qian, D.; Zhang, J. Beilstein J. Org. Chem. 2011, 7, 808.   DOI   ScienceOn
21 Valizadeh, H.; Amiri, M.; Gholipur, H. J. Heterocyclic Chem. 2009, 46, 108.   DOI
22 Merkul, E.; Urselmann, D.; Muller, T. J. J. Eur. J. Org. Chem. 2011, 238.
23 Chen, S.-N.; Wu, W.-Y.; Tsai, F.-Y. Green Chem. 2009, 11, 269.   DOI   ScienceOn
24 Zhou, L.; Zhan, H.-Y.; Liu, H.-L.; Jiang, H.-F. Chin. J. Chem. 2007, 25, 1413.   DOI   ScienceOn
25 Stefani, H. A.; Pena, J. M.; Zukerman-Schpector, J.; Tiekink, E. R. T. J. Braz. Chem. Soc. 2011, 22, 1439.
26 Kurita, T.; Abe, M.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Synlett. 2007, 16, 2521.
27 (b) Melhado, A. D.; Brenzovich, W. E., Jr.; Lackner, A. D.; Toste, F. D. J. Am. Chem. Soc. 2010, 132, 8885.   DOI   ScienceOn
28 (c) Brenzovich, W. E., Jr.; Benitez, D.; Lackner, A. D.; Shunatona, H. P.; Tkatchouk, E.; Goddard, W. A., III.; Toste, F. D. Angew. Chem., Int. Ed. 2010, 49, 5519.   DOI   ScienceOn
29 (e) Peng, Y.; Cui, L.; Zhang, G..; Zhang, L. J. Am. Chem. Soc. 2009, 131, 5062.   DOI   ScienceOn
30 (f) Zhang, G.; Peng, Y.; Cui, L.; Zhang, L. Angew. Chem., Int. Ed. 2009, 48, 3112.   DOI   ScienceOn
31 Praveen, C.; Kalyanasundaram, A.; Perumal, P. T. Synlett 2010, 777.
32 (a) Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 5096.   DOI   ScienceOn
33 (b) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.   DOI   ScienceOn
34 (c) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.   DOI   ScienceOn
35 (d) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 13978.   DOI   ScienceOn
36 (e) Kaye, S.; Fox, J. M.; Hicks, F. A.; Buchwald, S. L. Adv. Synth. Catal. 2001, 343, 789.   DOI
37 Zhang, G.; Luo, Y.; Wang, Y.; Zhang, L. Angew. Chem. Int. Ed. 2011, 50, 4450.   DOI
38 (a) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C.-H. Angew. Chem. Int. Ed. 2005, 44, 192.   DOI   ScienceOn
39 (b) Stavber, S.; Zupan, M. Acta Chim. Slov. 2005, 52, 13.
40 Grecian, S.; Fokin, V. V. Angew. Chem. 2008, 120, 8409.   DOI   ScienceOn
41 (a) Ueda, M.; Sugita, S.; Sato, A.; Miyoshi, T.; Miyata, O. J. Org. Chem. 2012, 77, 9344.   DOI   ScienceOn
42 (b) She, Z.; Niu, D.; Chen, L.; Gunawan, M. A.; Shanja, X.; Hersh, W. H.; Chen, Y. J. Org. Chem. 2012, 77, 3627.   DOI   ScienceOn
43 (c) Gayon, E.; Quinonero, O.; Lemouzy, S.; Vrancken, E.; Campagne, J.-M. Org. Lett. 2011, 13, 6418.   DOI   ScienceOn
44 (d) Ueda, M.; Sato, A.; Ikeda, Y.; Miyoshi, T.; Naito, T.; Miyata, O. Org. Lett. 2010, 12, 2594.   DOI   ScienceOn
45 (a) Sengupta, S.; Shi, X. ChemCatChem. 2010, 2, 609.   DOI
46 (b) Shapiro, N. D.; Toste, F. D. Synlett 2010, 675.
47 (c) Muzart, J. Tetrahedron 2008, 64, 5815.   DOI   ScienceOn
48 (d) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.   DOI   ScienceOn
49 (e) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.   DOI   ScienceOn
50 Leyva-Perez, A.; Domenech, A.; Al-Resayes, S. I.; Corma, A. ACS Catal. 2012, 2, 121.   DOI   ScienceOn
51 (d) Hopkinson, M. N.; Ross, J. E.; Giuffredi, G. T.; Gee, A. D.; Gouverneur, V. Org. Lett. 2010, 12, 4904.   DOI   ScienceOn
52 Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874.   DOI   ScienceOn
53 (l) Furstner, A. Chem. Soc. Rev. 2009, 38, 3208.   DOI   ScienceOn
54 Kumbhare, R. M.; Kosurkar, U. B.; Ramaiah, M. J.; Dadmal, T. L.; Pushpavalli, S. N. C. V. L.; Pal-Bhadra, M. Bioorg. Med. Chem. Lett. 2012, 22, 5424.   DOI   ScienceOn