Efficient copper-catalyzed synthesis of 2-amino-4(3h)-quinazolinone and 2-aminoquinazoline derivatives

Synthesis

Volumn , Issue 16, 2009, Pages 2679-2688

  Huang, Xuhu ^a   Yang, Haijun ^a   Fu, Hua ^a   Qiao, Renzhong ^a   Zhao, Yufen ^a  

^a Tsinghua University   (China)

Author keywords

2 amino 4(3H) quinazolinone; 2 aminoquinazoline; Copper catalyzed; Cross coupling; Synthetic method

Indexed keywords

2-AMINO-4(3H)-QUINAZOLINONE; 2-AMINOQUINAZOLINE; CATALYZED SYNTHESIS; COPPER IODIDE; CROSS-COUPLING; EFFICIENT METHOD; MEDICINAL CHEMISTRY; N-HETEROCYCLES; ORGANIC CHEMISTRY; STARTING MATERIALS; SYNTHETIC METHOD;

AMINATION; AMINES; KETONES;

COPPER;

2 (4 METHYLPIPERAZIN 1 YL)QUINAZOLIN 4(3H) ONE; 2 (4 METHYLPIPERAZIN 1 YL)QUINAZOLINE; 2 (MORPHOLIN 1 YL)QUINAZOLIN 4(3H) ONE; 2 (MORPHOLIN 1 YL)QUINAZOLINE; 2 (PIPERIDIN 1 YL)QUINAZOLIN 4(3H) ONE; 2 (PIPERIDIN 1 YL)QUINAZOLINE; 2 (PYRROLIDIN 1 YL)QUINAZOLIN 4(3H) ONE; 2 (PYRROLIDIN 1 YL)QUINAZOLINE; 2 AMINO 4 PHENYLQUINAZOLINE; 2 AMINOQUINAZOLIN 4(3H) ONE; 2 AMINOQUINAZOLINE; 4 METHYL 2 (4 METHYLPIPERAZIN 1 YL)QUINAZOLINE; 4 METHYL 2 (MORPHOLIN 1 YL)QUINAZOLINE; 4 METHYL 2 (PIPERIDIN 1 YL)QUINAZOLINE; 4 METHYL 2 (PYRROLIDIN 1 YL)QUINAZOLINE; 4 METHYL 2 AMINOQUINAZOLINE; 4 PHENYL 2 (4 METHYLPIPERAZIN 1 YL)QUINAZOLINE; 4 PHENYL 2 (MORPHOLIN 1 YL)QUINAZOLINE; 4 PHENYL 2 (PIPERIDIN 1 YL)QUINAZOLINE; 4 PHENYL 2 (PYRROLIDIN 1 YL)QUINAZOLINE; 6 CHLORO (4 METHYLPIPERAZIN 1 YL)QUINAZOLIN 4(3H) ONE; 6 CHLORO 2 (MORPHOLIN 1 YL)QUINAZOLIN 4(3H) ONE; 6 CHLORO 2 (PIPERIDIN 1 YL)QUINAZOLIN 4(3H) ONE; 6 CHLORO 2 (PYRROLIDIN 1 YL)QUINAZOLIN 4(3H) ONE; BENZALDEHYDE DERIVATIVE; COPPER; GUANIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG SYNTHESIS;

EID: 70449396611     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216871     Document Type: Article

References (64)

1. Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093.
2. de Laszlo, S. E.; Chang, R. S.; Cheng, T. B.; Faust, K. A.; Greenlee, W. J.; Kivlighn, S. D.; Lotti, V. J.; O'Malley, S. S.; Schorn, T. W.; Siegl, P. K.; Tran, J.; Zingaro, G. J. Bioorg. Med. Chem. Lett. 1995, 5, 1359.
3. Johne, S. Pharmazie 1981, 36, 583.
4. Pendergast, W.; Johnson, J. V.; Dickerson, S. H.; Dev, I. K.; Duch, D. S.; Ferone, R.; Hall, W. R.; Humphrey, J.; Kelly, J. M.; Wilson, D. C. J. Med. Chem. 1993, 36, 2279.
5. Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128.
6. Grosso, J. A.; Nichols, E. D.; Kohli, J. D.; Glock, D. J. Med. Chem. 1982, 25, 703.
7. Somers, F.; Ouedraogo, R.; Antoine, M.-H.; de Tullio, P.; Becker, B.; Fontaine, J.; Damas, J.; Dupont, L.; Rigo, B.; Delarge, J.; Lebrun, P.; Pirotte, B. J. Med. Chem. 2001, 44, 2575.
8. Alagarsamy, V.; Dhanabal, K.; Parthiban, P.; Anjana, G.; Deepa, G.; Murugesan, B.; Rajkumar, S.; Beevi, A. J. J. Pharm. Pharmacol. 2007, 59, 669.
9. Hess, H.-J.; Cronin, T. H.; Scriabine, A. J. Med. Chem. 1968, 11, 130.
10. Hussain, M. A.; Chiu, A. T.; Price, W. A.; Timmermans, P. B.; Shefter, E. Pharm. Res. 1988, 5, 242.
11. Hrtner, S. R.; Ritschel, T.; Stengl, B.; Kramer, C.; Schweizer, W. B.; Wagner, B.; Kansy, M.; Klebe, G.; Diederich, F. Angew. Chem. Int. Ed. 2007, 46, 8266.
12. Liu, H.; Gao, J.; Kool, E. T. J. Org. Chem. 2005, 70, 639.
13. Ogawa, N.; Yoshida, T.; Aratani, T.; Koshinaha, E.; Kato, H.; Ito, Y. Chem. Pharm. Bull. 1988, 36, 2955.
14. McNamara, D. J.; Berman, E. M.; Fry, D. W.; Werbel, L. M. J. Med. Chem. 1990, 33, 2045.
15. Levin, J. I.; Fanshawe, W. J.; Epstein, J. W.; Beer, B.; Bartus, R. T.; Dean, R. L. Bioorg. Med. Chem. Lett. 1992, 2, 349.
16. Chao, Q.; Deng, L.; Shih, H.; Leoni, L. M.; Genini, D.; Carson, D. A.; Cottam, H. B. J. Med. Chem. 1999, 42, 3860.
17. Smits, R. A.; Lim, H. D.; Hanzer, A.; Zuiderveld, O. P.; Guaita, E.; Adami, M.; Coruzzi, G.; Leurs, R.; de Esch, I. J. P. J. Med. Chem. 2008, 51, 2457.
18. Hu, E.; Tasker, A.; White, R. D.; Kunz, R. K.; Human, J.; Chen, N.; Bürli, R.; Hungate, R.; Novak, P.; Itano, A.; Zhang, X.; Yu, V.; Nguyen, Y.; Tudor, Y.; Plant, M.; Flynn, S.; Xu, Y.; Meagher, K. L.; Whittington, D. A.; Ng, G. Y. J. Med. Chem. 2008, 51, 3065.
19. Li, J.-S.; Fan, Y.-H.; Zhang, Y.; Marky, L. A.; Gold, B. J. Am. Chem. Soc. 2003, 125, 2084.
20. For a recent review, see: Vögtle, M. M.; Marzinzik, A. L. QSAR Comb. Sci. 2004, 23, 440.
21. Kundu, B.; Partani, P.; Duggineni, S.; Sawant, D. J. Comb. Chem. 2005, 7, 909.
22. Wéber, C.; Demeter, A.; Szendrei, G. I.; Greiner, I. Tetrahedron Lett. 2003, 44, 7533.
23. Yang, R.-Y.; Kaplan, A. Tetrahedron Lett. 2000, 41, 7005.
24. Gopalsamy, A.; Yang, H. J. Comb. Chem. 2000, 2, 378.
25. Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 5831.
26. Wilson, L. J. Org. Lett. 2001, 3, 585.
27. Villalgordo, J. M.; Obrecht, D.; Chucholowsky, A. Synlett 1998, 1405.
28. Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron 1989, 45, 4263.
29. Zhang, W.; Mayer, J. P.; Hall, S. E.; Weigel, J. A. J. Comb. Chem. 2001, 3, 255.
30. Larksarp, C.; Alper, H. J. Org. Chem. 2000, 65, 2773.
31. Fray, M. J.; Mathias, J. P.; Nichols, C. L.; Po-Ba, Y. M.; Snow, H. Tetrahedron Lett. 2006, 47, 6365.
32. Zeghida, W.; Debray, J.; Chierici, S.; Dumy, P.; Demeunynck, M. J. Org. Chem. 2008, 73, 2473.
33. For recent reviews on copper-catalyzed N-arylation, see: Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
34. Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400.
35. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
36. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054; and references cited therein.
37. Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2005, 70, 8107.
38. Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Eur. J. 2006, 12, 3636.
39. Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672.
40. Jiang, Q.; Jiang, D.; Jiang, Y.; Fu, H.; Zhao, Y. Synlett 2007, 1836.
41. Guo, X.; Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Catal. 2006, 348, 2197.
42. Liu, X.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem. Int. Ed. 2009, 48, 348.
43. Huang, C.; Fu, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Commun. 2008, 6333.
44. Yang, D.; Fu, H.; Hu, L.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 7841.
45. Martin, R.; Rodríguez, R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 7079.
46. Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
47. Bonnaterre, F.; Bois-Choussy, M.; Zhu, J. Org. Lett. 2006, 8, 4351.
48. Zou, B.; Yuan, Q.; Ma, D. Angew. Chem. Int. Ed. 2007, 46, 2598.
49. Yuan, X.; Xu, X.; Zhou, X.; Yuan, J.; Mai, L.; Li, Y. J. Org. Chem. 2007, 72, 1510.
50. Nicolaou, K. C.; Boddy, C. N. C.; Natarajar, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421.
51. Lindley, J. Tetrahedron 1984, 40, 1433.
52. Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986.
53. Cai, Q.; Zou, B.; Ma, D. Angew. Chem. Int. Ed. 2006, 45, 1276.
54. Plaskon, A. S.; Ryabukhin, S. V.; Volochnyuk, D. M. Synthesis 2008, 1069.
55. Dean, W. D.; Papadopoulos, E. P. J. Heterocycl. Chem. 1982, 19, 1117.
56. Weber, C.; Szendrei, G. I.; Greiner, I. Pharma. Chem. 2003, 2, 25.
57. George, B. J.; Dib, H. H. Tetrahedron 2006, 62, 1182.
58. Leonard, N. J.; Kazmierczak, F.; Rykowski, A. Z. J. Org. Chem. 1987, 52, 2933.
59. Ram, V. J.; Farhanullah; Tripathi, B. K.; Srivastava, A. K. Bioorg. Med. Chem. 2003, 11, 2439.
60. Henriksen, S. T.; Sorensen, U. S. Tetrahedron Lett. 2006, 47, 8251.
61. Sasse, K. Synthesis 1978, 379.
62. Kvaskoff, D.; Bednarek, P.; George, L.; Waich, K.; Wentrup, C. J. Org. Chem. 2006, 71, 4049.
63. Gomez, P. V.; Madronero, R.; Vega, S. Synthesis 1977, 345.
64. Kamal, A.; Rao, M. V.; Sattur, P. B. Heterocycles 1986, 24, 3075.