Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums

Journal of Organic Chemistry

Volumn 80, Issue 14, 2015, Pages 7099-7107

  Feng, Yadong ^a   Li, Yudong ^a   Cheng, Guolin ^a   Wang, Lianhui ^a   Cui, Xiuling ^a  

^a HUAQIAO UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER;

COPPER CATALYZED; ENVIRONMENTAL FRIENDLINESS; MILD REACTION CONDITIONS; QUINAZOLINONES; SIMPLE OPERATION;

AMINES;

2 (2,4 DICHLOROPHENYL) 3 PHENETHYLQUINAZOLIN 4(3H) ONE; 2 (4 BROMOPHENYL) 3 PHENETHYLQUINAZOLIN 4(3H) ONE; 2 (4 CHLOROPHENYL) 3 PHENETHYLQUINAZOLIN 4(3H) ONE; 2 (4 FLUOROPHENYL) 3 PHENETHYLQUINAZOLIN 4(3H) ONE; 2 (4 METHOXYPHENYL) 3 PHENETHYLQUINAZOLIN 4(3H) ONE; 2 (NAPHTHALEN 2 YL) 3 PHENETHYLQUINAZOLIN 4(3H) ONE; 2 ARYLINDOLE DERIVATIVE; 2 ARYLQUINAZOLINONE DERIVATIVE; 2 PHENYL 3 (3 PHENYLPROPYL)QUINAZOLIN 4(3H) ONE; 2 PHENYL 3 [4 (TRIFLUOROMETHYL)BENZYL]QUINAZOLIN 4(3H) ONE; 3 BENZYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 3 BUTYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 3 DODECYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 3 ETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 3 PHENETHYL 2 (M TOLYL)QUINAZOLIN 4(3H) ONE; 3 PHENETHYL 2 (O TOLYL)QUINAZOLIN 4(3H) ONE; 3 PHENETHYL 2 (P TOLYL)QUINAZOLIN 4(3H) ONE; 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 3 PHENETHYL 2 [4 (TRIFLUOROMETHYL)PHENY]QUINAZOLIN 4(3H) ONE; 3 [4 (TERT BUTYL)BENZYL] 2 PHENYLQUINAZOLIN 4(3H) ONE; 6 BROMO 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 6 CHLORO 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 6 FLUORO 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 6 ISOPROPYL 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 6 METHYL 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 7 FLUORO 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; 7 METHYL 3 PHENETHYL 2 PHENYLQUINAZOLIN 4(3H) ONE; INDOLE DERIVATIVE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; AMINE; AMMONIUM DERIVATIVE; COPPER;

AMINATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; HYDROLYSIS; OXIDATION; REACTION ANALYSIS; REACTION TIME; STEREOSPECIFICITY; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINES; AMMONIUM COMPOUNDS; CATALYSIS; COPPER; INDOLES; MOLECULAR STRUCTURE; QUINAZOLINONES;

EID: 84937561831     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00957     Document Type: Article

References (50)

1. Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787-9826
2. Nanda, A. K.; Ganguli, S.; Chakraborty, R. Molecules 2007, 12, 2413-2426
3. Chan, J.-H.; Hong, J.-S.; Kuyper, L. F.; Baccanari, D. P.; Joyner, S. S.; Tansik, R. L.; Boytos, C. M.; Rudolph, S. K. J. Med. Chem. 1995, 38, 3608-3616
4. Kikuchi, H.; Yamamoto, K.; Horoiwa, S.; Hirai, S.; Kasahara, R.; Hariguchi, N.; Matsumoto, M.; Oshima, Y. J. Med. Chem. 2006, 49, 4698-4706
5. Takase, Y.; Saeki, T.; Watanabe, N.; Adachi, H.; Souda, S.; Saito, I. J. Med. Chem. 1994, 37, 2106-2111
6. Dupuy, M.; Pinguet, F.; Chavignon, O.; Chezal, J. M.; Teulade, J. C.; Chapat, J. P.; Blache, Y. Chem. Pharm. Bull. 2001, 49, 1061-1065
7. Chandrika, P. M.; Yakaiah, T.; Rao, A. R. R.; Narsaiah, B.; Reddy, N. C.; Sridhar, V.; Rao, J. V. Eur. J. Med. Chem. 2008, 43, 846-852
8. Yen, M.-H.; Sheu, J.-R.; Peng, I.-H.; Lee, Y.-M.; Chern, J.-W. J. Pharm. Pharmacol. 1996, 48, 90-95
9. Kunes, J.; Bazant, J.; Pour, M.; Waisser, K.; Slosarek, M.; Janota, J. Farmaco. 2000, 55, 725-729
10. Waisser, K.; Gregor, J.; Dostal, H.; Kunes, J.; Kubicova, L.; Klimesova, V.; Kaustova, J. Farmaco. 2001, 56, 803-807
11. Archana, A.; Shrivastava, V. K.; Chandra, R.; Kumar, A. Indian J. Chem. 2002, 41B, 2371-2375
12. Matsuno, K.; Ushiki, J.; Seishi, T.; Ichimura, M.; Giese, N. A.; Yu, J.-C.; Takahashi, S.; Oda, S.; Nomoto, Y. J. Med. Chem. 2003, 46, 4910-4925
13. Baba, A.; Kawamura, N.; Makino, H.; Ohta, Y.; Taketomi, S.; Sohda, T. J. Med. Chem. 1996, 39, 5176-5182
14. Daniel, B. Y.; Jason, W. G.; Stephanie, L. S.; Arely, V. P.; Matthew, T. C.; David, A. B. J. Dermatol. Sci. 2006, 42, 13-21
15. Malecki, N.; Carato, P.; Rigo, G.; Goossens, J. F.; Houssin, R.; Bailly, C.; Henichart, J. P. Bioorg. Med. Chem. 2004, 12, 641-647
16. Rudolph, J.; Esler, W. P.; O'Connor, S.; Coish, P. D. G.; Wickens, P. L.; Brands, M.; Bierer, D. E.; Bloomquist, B. T.; Bondar, G.; Chen, L.; Chuang, C.-Y.; Claus, T. H.; Fathi, Z.; Fu, W.; Khire, U. R.; Kristie, J. A.; Liu, X.-G.; Lowe, D. B.; McClure, A. C.; Michels, M.; Ortiz, A. A.; Ramsden, P. D.; Schoenleber, R. W.; Shelekhin, T. E.; Vakalopoulos, A.; Tang, W.; Wang, L.; Yi, L.; Gardell, S. J.; Livingston, J. N.; Sweet, L. J.; Bullock, W. H. J. Med. Chem. 2007, 50, 5202-5216
17. Zhang, X.-D.; Ye, D.-J.; Sun, H.-F.; Guo, D.-L.; Wang, J.; Huang, H.; Zhang, X.; Jiang, H.-L.; Liu, H. Green Chem. 2009, 11, 1881-1888
18. Xu, W.; Jin, Y.-B.; Liu, H.-X.; Jiang, Y.-Y.; F, H. Org. Lett. 2011, 13, 1274-1277
19. Xu, L.; Jiang, Y.; Ma, D. Org. Lett. 2012, 14, 1150-1153
20. Witt, A.; Bergman, J. Curr. Org. Chem. 2003, 7, 659-677
21. Connolly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J. Tetrahedron. 2005, 61, 10153-10202
22. Dabiri, M.; Baghbanzadeh, M.; Delbari, S. J. Comb. Chem. 2008, 10, 700-703
23. Wu, H.; Xie, X.; Liu, G. J. Comb. Chem. 2010, 12, 346-355
24. Feng, E.; Zhou, Y.; Zhang, D.; Zhang, L.; Sun, H.; Jiang, H.; Liu, H. J. Org. Chem. 2010, 75, 3274-3282
25. Heravi, M. M.; Tavakoli-Hoseini, N.; Bamoharram, F. F. Synth. Commun. 2011, 41, 707-714
26. Zhou, J.; Fang, J. J. Org. Chem. 2011, 76, 7730-7736
27. Tavakoli-Hoseini, N.; Davoodnia, A. Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 2012, 42, 76-81
28. Watson, A. J. A; Maxwell, A. C.; Williams, J. M. J. Org. Biomol. Chem. 2012, 10, 240-243
29. Hikawa, H.; Ino, Y.; Suzuki, H.; Yokoyama, Y. J. Org. Chem. 2012, 77, 7046-7051
30. Zhu, Y.-P.; Fei, Z.; Liu, M.-C.; Jia, F.-C.; Wu, A.-X. Org. Lett. 2013, 15, 378-381
31. Soliman, R.; Soliman, F. S. G. Synthesis 1979, 803-804
32. Ramana, D. V.; Kantharaj, E. Indian J. Heterocycl. Chem. 1994, 3, 215-218
33. Xu, W.; Fu, H. J. Org. Chem. 2011, 76, 3846-3852
34. Wu, X.-F.; He, L.; Neumann, H.; Beller, M. Chem.-Eur. J. 2013, 19, 12635-12638
35. Nguyen, T. B.; Bescont, J. L.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2013, 15, 6218-6221
36. Romero, A. H.; Salazar, J.; López, S. E. Synthesis 2013, 45, 2043-2050
37. Cheng, R.; Guo, T.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Synthesis 2013, 45, 2998-3006
38. Nakano, H.; Kutsumura, N.; Saito, T. Synthesis 2012, 44, 3179-3184
39. Adib, M.; Sheikhi, E.; Bijanzadeh, H. R. Synlett 2012, 23, 85-88
40. Shcherbakova, I.; Balandrin, M.; Fox, J.; Heaton, W.; Conklin, R.; Papac, D. PCT Int. Appl. 2004, 5, 77
41. Dandia, A.; Singh, R.; Sarawgi, P. Org. Prep. Proced. Int. 2005, 37, 397-402
42. Wang, L.; Wang, Y.; Chen, M.; Ding, M. W. Adv. Synth. Catal. 2014, 356, 1098-1104
43. Sadig, J. E. R.; Foster, R.; Wakenhut, F.; Willis, M. C. J. Org. Chem. 2012, 77, 9473-9486
44. Ma, B.; Wang, Y.; Peng, J.; Zhu, Q. J. Org. Chem. 2011, 76, 6362-6366
45. Jiang, X.; Tang, T.; Wang, J.-M.; Chen, Z.; Zhu, Y.-M.; Ji, S.-J. J. Org. Chem. 2014, 79, 5082-5087
46. Zheng, Z. Y.; Alper, H. Org. Lett. 2008, 10, 829-832
47. Yamashita, M.; Iida, A. Tetrahedron Lett. 2014, 55, 2991-2993
48. Lian, X.-L.; Lei, H.; Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Chem. Commun. 2013, 8196-8198
49. Nelson, A. C.; Lei, H.; Kalinowski, E. S.; Czerniecki, N. J.; Jacobson, T. L.; Grundt, P. Org. Biomol. Chem. 2013, 11, 7455-7457
50. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357-2367