One-pot synthesis of 3-hydroxyquinolin-2(1 H)-ones from N-phenylacetoacetamide via PhI(OCOCF3)2-mediated α-hydroxylation and H2SO4-promoted intramolecular cyclization

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5385-5392

  Yuan, Yucheng ^a   Yang, Rui ^a   Zhang Negrerie, Daisy ^a   Wang, Junwei ^a   Du, Yunfei ^a   Zhao, Kang ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLATION;

HYDROXYL GROUPS; INTRAMOLECULAR CONDENSATION; INTRAMOLECULAR CYCLIZATIONS; ONE-POT SYNTHESIS;

CYCLIZATION;

1 BENZYL 3 HYDROXY 4 METHYLQUINOLIN 2(1H) ONE; 1 BENZYL 7 FLUORO 3 HYDROXY 4 METHYLQUINOLIN 2(1H) ONE; 3 HYDROXY 1 METHYL 4 PHENYLQUINOLIN 2(1H) ONE; 3 HYDROXY 1,4 DIMETHYLQUINOLIN 2(1H) ONE; 3 HYDROXY 1,4,6 TRIMETHYLQUINOLIN 2(1H) ONE; 3 HYDROXY 4 (3 METHOXYPHENYL)QUINOLIN 2(1H) ONE; 3 HYDROXY 4 4 TOLYLQUINOLIN 2(1H ) ONE; 3 HYDROXY 4 ISOBUTYLQUINOLIN 2(1H) ONE; 3 HYDROXY 4 METHYL PHENYLQUINOLIN 2(1H) ONE; 3 HYDROXY 4 METHYLQUINOLIN 2(1H) ONE; 3 HYDROXY 4,8 DIMETHYLQUINOLIN 2(1H) ONE; 3 HYDROXY 6 IODO 4 PHENYLQUINOLIN 2(1H ) ONE; 3 HYDROXY 6 METHOXY 4 METHYLQUINOLIN 2(1H) ONE; 3 HYDROXY 7 METHOXY 4 METHYLQUINOLIN 2(1H) ONE; 3 HYDROXYQUINOLIN2(1H) ONE DERIVATIVE; 4 (3 BROMOPHENYL) 3 HYDROXYQUINOLIN 2(1H) ONE; 4 (4 FLUOROPHENYL) 3 HYDROXYQUINOLIN 2(1H) ONE; 6 BROMO 3 HYDROXY 1,4 DIMETHYLQUINOLIN 2(1H) ONE; 7 FLUORO 3 HYDROXY 4 METHYLQUINOLIN 2(1H) ONE; 8 CHLORO 3 HYDROXY 4 METHYLQUINOLIN 2(1H) ONE; CARBON; HYDROXYL GROUP; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; VIRIDICATIN;

ARTICLE; COVALENT BOND; CYCLIZATION; DRUG SYNTHESIS; HYDROXYLATION; ONE POT SYNTHESIS; POLYMERIZATION;

EID: 84879323632     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400541s     Document Type: Article

References (51)

1. Sit, S. Y.; Ehrgott, F. J.; Gao, J.; Meanwell, N. A. Bioorg. Med. Chem. Lett. 1996, 6, 499
2. Ribeiro, N.; Tabaka, H.; Peluso, J.; Fetzer, L.; Nebigil, C.; Dumont, S.; Muller, C. D.; Desaubry, L. Bioorg. Med. Chem. Lett. 2007, 17, 5523
3. Chen, M. H.; Fitzgerald, P.; Singh, S. B.; O'Neill, E. A.; Schwartz, C. D.; Thompson, C. M.; O'Keefe, S. J.; Zaller, D. M.; Doherty, J. B. Bioorg. Med. Chem. Lett. 2008, 18, 2222
4. Anzini, M.; Cappelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B. M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J. C. J. Med. Chem. 1995, 38, 2692
5. He, J.; Lion, U.; Sattler, I.; Gollmick, F. A.; Grabley, S.; Cai, J.; Meiners, M.; Schunke, H.; Schaumann, K.; Dechert, U.; Krohn, M. J. Nat. Prod. 2005, 68, 1397
6. Toum, J.; Moquette, A.; Lamotte, Y.; Mirguet, O. Tetrahedron Lett. 2012, 53, 1920
7. Gioiello, A.; Venturoni, F.; Marinozzi, M.; Natalini, B.; Pellicciari, R. J. Org. Chem. 2011, 76, 7431
8. Heguy, A.; Cai, P.; Meyn, P.; Houck, D.; Russo, S.; Michitsch, R.; Pearce, C.; Katz, B.; Bringmann, G.; Feineis, D.; Taylor, D. L.; Tyms, A. S. Antiviral Chem. Chemother. 1998, 9, 149
9. Aoki, Y.; Ishiwara, M.; Koda, A.; Takagaki, H. Eur. J. Pharmacol. 2000, 409, 325
10. Ishiwara, M.; Aoki, Y.; Takagaki, H.; Ui, M.; Okajima, F. J. Pharmacol. Exp. Ther. 2003, 307, 583
11. Kimura, N.; Fukui, H.; Takagaki, H.; Yonemochi, E.; Terada, K. Chem. Pharm. Bull. 2001, 49, 1321
12. Mizutani, N.; Aoki, Y.; Nabe, T.; Ishiwara, M.; Yoshino, S.; Takagaki, H.; Kohno, S. Eur. J. Pharmacol. 2009, 602, 138
13. Suchaud, V.; Bailly, F.; Lion, C.; Tramontano, E.; Esposito, F.; Corona, A.; Christ, F.; Debyser, Z.; Cotelle, P. Bioorg. Med. Chem. Lett. 2008, 22, 3988
14. Duplantier, A. J.; Becker, S. L.; Bohanon, M. J.; Borzilleri, K. A.; Chrunyk, B. A.; Downs, J. T.; Hu, L. Y.; El-Kattan, A.; James, L. C.; Liu, S.; Maklad, N.; Mansour, M. N.; Mente, S.; Piotrowski, M. A.; Sakya, S. M.; Sheehan, S.; Steyn, S. J.; Strick, C. A.; Williams, V. A.; Zhang, L. J. Med. Chem. 2009, 52, 3576
15. Sit, S. Y.; Meanwell, N. A. U.S. Patent 5,892,045, 1999.
16. Greibrokk, T.; Undheim, K. Acta Chem. Scand. 1971, 25, 2935
17. Johnsen, B. A.; Undheim, K. Acta Chem. Scand. 1984, 38, 109
18. Huntress, E. H.; Bornstein, J.; Hearon, W. M. J. Am. Chem. Soc. 1956, 78, 2225
19. Kobayashi, Y.; Harayama, T. Org. Lett. 2009, 11, 1603
20. Arshad, N.; Hashim, J.; Kappe, C. O. J. Org. Chem. 2008, 73, 4755
21. White, J. D.; Dimsdale, M. J. Chem. Commun. 1969, 1285
22. Martin, P. K.; Rapoport, H.; Smith, H. W.; Wong, J. L. J. Org. Chem. 1969, 34, 1359
23. Smith, H. W.; Rapoport, H. J. Am. Chem. Soc. 1969, 81, 6083
24. Terada, A.; Yabe, Y.; Miyadera, T.; Tachikawa, R. Chem. Pharm. Bull. 1973, 21, 807
25. Wang, J.; Yuan, Y.; Xiong, R.; Zhang-Neigrerie, D.; Du, Y.; Zhao, K. Org. Lett. 2012, 14, 2210
26. Sai, K. K. S.; Esteves, P. M.; Penha, E. T.; Klumpp, D. A. J. Org. Chem. 2008, 73, 6506
27. Knorr, L. Ann. Chem. 1886, 236, 69
28. Kaslow, C. E.; Cook, D. J. J. Am. Chem. Soc. 1945, 67, 1969
29. Hauser, C. R.; Reynolds, G. A. J. Am. Chem. Soc. 1948, 70, 2402
30. Liu, W. B.; Chen, C.; Zhang, Q.; Zhu, Z. B. Beilstein J. Org. Chem. 2011, 7, 1436
31. Forbis, R. M.; Rinehart, K. L., Jr. J. Am. Chem. Soc. 1973, 95, 5003
32. Nadzan, A. M.; Rinehart, K. L., Jr. J. Am. Chem. Soc. 1977, 99, 4647
33. Maiti, A.; Reddy, P. V. N.; Sturdy, M.; Marler, L.; Pegan, S. D.; Pezzuto, J. M.; Cushman, M. J. Med. Chem. 2009, 52, 31873
34. Kurouchi, H.; Kawamoto, K.; Sugimoto, H.; Nakamura, S.; Otani, Y.; Ohwada, T. J. Org. Chem. 2012, 77, 9313
35. Barluenga, J.; Bayon, A. M.; Asensio, G. Chem. Commun. 1984, 1334
36. Panfilov, A. V.; Markovich, Yu. D.; Zhirov, A. A.; Ivashev, I. P.; Kirsanov, A. T.; Kondrat'ev, V. B. Pharm. Chem. J. 2000, 34, 371
37. Robert, C. K. J. Am. Chem. Soc. 1952, 74, 5536
38. Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2417
39. Anwar, M.; Moloney, M. G. Tetrahedron Lett. 2007, 48, 7259
40. Yadlapalli, R. K.; Chourasia, O. P.; Vemuri, K.; Sritharan, M.; Perali, R. S. Bioorg. Med. Chem. Lett. 2012, 22, 2708
41. Shawali, A. S. A. S.; Naoum, M. M.; Ibrahim, S. A. Bull. Chem. Soc. Jpn. 1972, 45, 2504
42. Maiti, A.; Reddy, P. V. N.; Cushman, M.; Sturdy, M.; Pegan, S. D.; Mesecar, A. D.; Marler, L.; Pezzuto, J. M. J. Med. Chem. 2009, 52, 1873
43. Etkin, N.; Badu, S. D.; Fooks, C. J.; Durst, T. J. Org. Chem. 1990, 55, 1093
44. Evertsson, E.; Ingharnd, T.; Lindberg, J.; Linusson, A.; Giordanetto, F. E.P. Patent 704,678, 2005.
45. Heitbaum, M.; Froehlich, R.; Glorius, F. Adv. Synth. Catal. 2010, 352, 357
46. Angelov, P. Synlett 2010, 8, 1273
47. Staskun, B.; Meltzer, P. C. Tetrahedron 1977, 33, 2429
48. Andreichikov, Yu. S. Zh. Org. Khim. 1988, 24, 210
49. Steinhuebel, D.; Sun, Y.; Matsumura, K.; Sayo, N.; Saito, T. J. Am. Chem. Soc. 2009, 131, 11316
50. Abou-Elenien, G. M.; El-Anadouli, B. E.; Bahgat, E.; Baraka, R. M. J. Chem. Soc., Perkin Trans. 2 1957, 79, 2919
51. Luchner, M.; Mohammed, Y. S. Tetrahedron Lett. 1964, 29, 1987