An efficient synthesis of 2-hydroxy-7,8-dihydroquinolin-5(6H)-ones and 7,8-dihydroquinoline-2,5(1H,6H)-diones from Morita-Baylis-Hillman adduct acetates

Synthesis

Volumn , Issue 16, 2008, Pages 2561-2568

  Zhong, Weihui ^a   Lin, Fuliang ^a   Chen, Ren'er ^a   Su, Weike ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

2 hydroxy 7,8 dihydroquinolin 5(6H) ones; 7,8 dihydroquinoline 2,5(1H,6H) diones; Cyclohexane 1,3 diones; Morita Baylis Hillman adduct acetates; Solvent free conditions

Indexed keywords

AMINES; AMMONIUM COMPOUNDS; ORGANIC COMPOUNDS;

2-HYDROXY-7,8-DIHYDROQUINOLIN-5(6H)-ONES; 7,8-DIHYDROQUINOLINE-2,5(1H,6H)- DIONES; CYCLOHEXANE-1,3-DIONES; MORITA-BAYLIS-HILLMAN ADDUCT ACETATES; SOLVENT-FREE CONDITIONS;

KETONES;

1 (3,4 DIFLUOROPHENYL) 7,7 DIMETHYL 3 (3 NITROBENZYL) 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 1 (4 CHLOROPHENYL) 7,7 DIMETHYL 3 (3 NITROBENZYL) 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 1 BUTYL 3 (4 FLUOROBENZYL) 7,7 DIMETHYL 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 1 METHOXYPHENYL 7,7 DIMETHYL 3 (3 NITROBENZYL) 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 2 HYDROXY 3 (3 METHOXYBENZYL) 7,8 DIHYDROQUINOLIN 5(6H) ONE; 2 HYDROXY 3 (3 NITROBENZYL) 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 2 HYDROXY 7,7 DIMETHYL 3 (3 METHOXYBENZYL) 7,8 DIHYDROQUINOLIN 5(6H) ONE; 2 HYDROXY 7,7 DIMETHYL 3 (3 NITROBENZYL) 7,8 DIHYDROQUINOLIN 5(6H) ONE; 2 HYDROXY 7,7 DIMETHYL 3 (THIEN 2 YLMETHYL) 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 (1,3 BENZODIOXOL 5 YLMETHYL) 2 HYDROXY 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 (2 CHLORO 6 FLUOROBENZYL) 2 HYDROXY 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 (2 CHLOROBENZYL) 2 HYDROXY 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 (3,4 DIMETHYLBENZYL) 1 (4 PHENYLTHIAZOL 2 YL) 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 3 (3,4 DIMETHYLBENZYL) 2 HYDROXY 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 (3,4 DIMETHYLBENZYL) 7,7 DIMETHYL 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 3 (4 FLUOROBENZYL) 2 HYDROXY 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 (4 FLUOROBENZYL) 2 HYDROXY 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 (FURAN 2 YLMETHYL) 2 HYDROXY 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 BENZYL 2 HYDROXY 7,7 DIMETHYL 7,8 DIHYDROQUINOLIN 5(6H) ONE; 3 BENZYL 2 HYDROXY 7,8 DIHYDROQUINOLIN 5(6H) ONE; 7,7 DIMETHYL 3 (3 NITROBENZYL) 1 (4 TOLYL) 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 7,7 DIMETHYL 3 (3 NITROBENZYL) 1 PHENYL 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; 7,7 DIMETHYL 3 PENTYL 7,8 DIHYDROQUINOLINE 2,5(1H,6H) DIONE; ACETIC ACID DERIVATIVE; AMMONIUM ACETATE; QUINOLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; ELECTRON TRANSPORT; MORITA BAYLIS HILLMAN REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; STEREOSPECIFICITY; TEMPERATURE;

EID: 50849137859     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078601     Document Type: Article

References (53)

1. (a) Raffaella, B.; Michele, F.; Paola, F.; Luisa, M. Quant. Struct.-Act. Relat. 1997, 16, 201.
2. (b) El-Sheikh, M. I.; Cook, J. M. J. Org. Chem. 1980, 45, 2585.
3. (a) Carlier, P. R.; Du, D. M.; Han, Y. F.; Liu, J.; Perola, E.; Williams, I. D.; Pang, Y. P. Angew. Chem. Int. Ed. 2000, 39, 1775.
4. (b) Rivikin, A.; Adams, B. Tetrahedron Lett. 2006, 47, 2395.
5. (c) Christos, A. M.; Alexandres, L. Z.; Olga, I. M. J. Org. Chem. 2003, 68, 4567.
6. (d) Pita, B.; Masaguer, C. F.; Ravina, E. Tetrahedron Lett. 2002, 43, 7929.
7. (e) Lee, Y. R.; Kweon, H. I.; Koh, W. S.; Min, K. R.; Kim, Y.; Lee, S. H. Synthesis 2001, 1851.
8. Anderson, W. K.; Dean, D. C.; Endo, T. J. Med. Chem. 1990, 33, 1667.
9. Pita, B.; Masaguer, C.F.; Raviña, E. Tetrahedron Lett. 2000, 41, 9829.
10. Li, Q.; Mitscher, L. A.; Shen, L. L. Med. Res. Rev. 2000, 20, 231.
11. (a) Gorobets, N. Y.; Yousefi, B. H.; Belaj, F.; Kappe, C. O. Tetrahedron 2004, 60, 8633.
12. (b) Dorigo, P.; Gaion, R. M.; Belluco, P.; Fraccarollo, D.; Maragno, I.; Bombierij, G.; Benetollo, F.; Mosti, L.; Orsinil, F. J. Med. Chem. 1993, 36, 2475.
13. Bar, G.; Parsons, A. F.; Thomas, C. B. Tetrahedron Lett. 2000, 41, 7751.
14. (a) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
15. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
16. (c) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
17. (a) Narender, P.; Gangadasu, B.; Ravinder, M.; Srinavas, U.; Swamy, G. Y. S. K.; Ravikumar, K.; Rao, V. J. Tetrahedron 2006, 62, 954.
18. (b) Berthiol, F.; Doucet, H.; Santelli, M. Tetrahedron 2006, 62, 4372.
19. (c) Madapa, S.; Singh, V.; Batra, S. Tetrahedron 2006, 62, 8740.
20. (d) Singh, V.; Kanojiya, S.; Batra, S. Tetrahedron 2006, 62, 10100.
21. (e) Lee, C. G.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron 2005, 61, 1493.
22. (f) Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron 2003, 59, 385.
23. (g) Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron 2002, 58, 3693.
24. (h) Im, Y. J.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2002, 43, 4675.
25. (a) Kantam, M. L.; Kumar, K. B. S.; Sreedhar, B. J. Org. Chem. 2008, 73, 320.
26. (b) He, L.; Jian, T. Y.; Ye, S. J. Org. Chem. 2007, 72, 7466.
27. (c) Pohamakotr, M.; Thamapipol, S.; Tuchinda, P.; Prabpai, S.; Kongsaeree, P.; Rutrakul, V. J. Org. Chem. 2007, 72, 5418.
28. (d) Park, H.; Cho, C. W.; Krische, M. J. J. Org. Chem. 2006, 71, 7892.
29. (e) Singh, V.; Saxena, R.; Batra, S. J. Org. Chem. 2005, 70, 353.
30. (f) Krishna, P. R.; Kannan, V.; Sharma, G. V. M. J. Org. Chem. 2004, 69, 6467.
31. (g) Kabalka, G. W.; Venkataiah, B.; Dong, G. J. Org. Chem. 2004, 69, 5807.
32. (h) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Acebes, R. R. J. Org. Chem. 2004, 69, 826.
33. (i) Kinoshita, H.; Osamura, T.; Kinoshita, S.; Iwamura, T.; Watanabe, S. I.; Kataoka, T.; Tanabe, G.; Muraoka, O. J. Org. Chem. 2003, 68, 7532.
34. (j) Reddy, M. V. R.; Rudd, M. T.; Ramachandran, P. V. J. Org. Chem. 2002, 67, 5382.
35. (k) Jauch, J. J. Org. Chem. 2001, 66, 609.
36. (l) Rafel, S.; Leahy, J. W. J. Org. Chem. 1997, 62, 1521.
37. (a) Ruda, M. C.; Bergman, J.; Koehler, K.; Liu, Y. Heterocycl. Commun. 2003, 9, 571.
38. (b) Al-Mousawi, S.; Abdel-Khalik, M. M.; John, E.; Elnagdi, M. H. J. Heterocycl. Chem. 2003, 40, 689.
39. (c) Carlier, P. R.; Du, D.; Han, Y.; Liu, J.; Pang, Y. Bioorg. Med. Chem. Lett. 1999, 9, 2335.
40. (d) Singh, K.; Singh, J.; Singh, H. Tetrahedron 1998, 54, 935.
41. (e) Gatta, F.; Del Giudice, M. R.; Pomponi, M.; Marta, M. Heterocycles 1992, 34, 991.
42. (f) Pettit, G. R.; Fleming, W. C.; Paull, K. D. J. Org. Chem. 1968, 33, 1089.
43. (g) Fossa, P.; Menozzi, G.; Dorigo, P.; Floreani, M.; Mosti, L. Bioorg. Med. Chem. 2003, 11, 4749.
44. (h) Oehldrich, J.; Cook, J. M. J. Org. Chem. 1977, 42, 889.
45. (i) Grizik, S. I.; Solov'eva, N. P.; Granik, V. G.; Yuzhakov, S. D.; Dolgun, O. V.; Dugin, S. F.; Medvedev, O. S.; Mashkovskii, M. D. Pharm. Chem. J. 1995, 29, 618.
46. (j) Abu-Shanab, F. A.; Redhouse, A. D.; Thompson, J. R.; Wakefield, B. J. Synthesis 1995, 557.
47. (a) Fernández, M.; Cuesta, E.; Avendaño, C. Heterocycles 1994, 38, 2615.
48. (b) Kočevar, M.; Polanc, S.; Tišler, M.; Verček, B. Heterocycles 1990, 30, 227.
49. (c) Fukatsu, H.; Kato, Y.; Murase, S.; Nakagawa, S. Heterocycles 1989, 29, 1517.
50. (d) Chang, J.-C.; El-Sheikh, M. I.; Cook, J. M. Heterocycles 1979, 12, 903.
51. (e) El-Sheikh, M. I.; Chang, J.-C.; Cook, J. M. Heterocycles 1978, 9, 1561.
52. Gowrisankar, S.; Na, J. E.; Lee, M. J.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 319.
53. Zhong, W.; Zhao, Y.; Su, W. Tetrahedron 2008, 64, 5491.