CuI-catalyzed C-N bond formation and cleavage for the synthesis of benzimidazo[1,2- a ]quinazoline derivatives

Journal of Organic Chemistry

Volumn 79, Issue 12, 2014, Pages 5847-5851

  Li, Chao ^a   Zhang, Wen Ting ^a   Wang, Xiang Shan ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE; REACTION KINETICS;

BOND CLEAVAGE REACTION; C-N BOND FORMATIONS; DOMINO REACTIONS; EFFICIENT STRATEGY; QUINAZOLINE DERIVATIVES; QUINAZOLINES; ULLMANN REACTION;

CATALYSIS;

2 CHLORO 9,10 DIMETHYLBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 2 CHLOROBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 2 FLUOROBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 2,3 DIMETHOXYBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 3 (1H BENZO[D]IMIDAZOL 2 YL) 2 (2 BROMOPHENYL) 2,3 DIHYDROQUINAZOLIN 4(1H) ONE; 3 (TRIFLUOROMETHYL)BENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 3 CHLOROBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 3 FLUOROBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 4 CHLOROBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 4 FLUOROBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; 9,10 DIMETHYLBENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; BENZIMIDAZO[1,2 A]QUINAZOLINE; BENZO[4,5]IMIDAZO[1,2 A]QUINAZOLINE; BENZO[4,5]IMIDAZO[1,2 A]THIENO[2,3 E]PYRIMIDINE; BENZO[4,5]IMIDAZO[1,2 A][1,3]DIOXOLO[4,5 G]QUINAZOLINE; COPPER; COPPER CHLORIDE; COPPER ION; N(2 BENZIMIDAZOLYL) 2 AMINOBENZAMIDE; PROLINE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; BENZALDEHYDE DERIVATIVE; BENZAMIDE DERIVATIVE; BENZIMIDAZO(1,2-A)QUINAZOLINE; BENZIMIDAZOLE DERIVATIVE; HALOGENATED HYDROCARBON; N-(2-BENZIMIDAZOLYL)-2-AMINOBENZAMIDE;

ARTICLE; CARBON NITROGEN RATIO; CATALYSIS; CHEMICAL REACTION; DRUG METABOLISM; DRUG SYNTHESIS; REACTION ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BENZALDEHYDES; BENZAMIDES; BENZIMIDAZOLES; CATALYSIS; COPPER; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; PROLINE; QUINAZOLINES;

EID: 84903150400     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5007398     Document Type: Article

References (50)

1. Abdel Gawad, N. M.; Georgey, H. H.; Youssef, R. M.; El-Sayed, N. A. Eur. J. Med. Chem. 2010, 45, 6058-6067
2. Kamal, A.; Vijaya Bharathi, E.; Janaki Ramaiah, M.; Dastagiri, D.; Surendranadha Reddy, J.; Viswanath, A.; Sultana, F.; Pushpavalli, S. N. C. V. L.; Pal-Bhadra, M.; Srivastava, H. K.; Narahari Sastry, G.; Juvekar, A.; Sen, S.; Zingde, S. Bioorg. Med. Chem. 2010, 18, 526-542
3. Evarts, J. B.; Ulrich, R. G. Preparation of atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives as anti-inflammatory and anticancer agents. PCT Int. Appl. WO 2010111432 A1, 30 Sep 2010
4. Chem. Abstr. 2010, 153, 456375.
5. Wu, H.; Xie, X.; Liu, G. J. Comb. Chem. 2010, 12, 346-355
6. Giri, R. S.; Thaker, H. M.; Giordano, T.; Williams, J.; Rogers, D.; Vasu, K. K.; Sudarsanam, V. Bioorg. Med. Chem. 2010, 18, 2796-2808
7. Giri, R. S.; Thaker, H. M.; Giordano, T.; Chen, B.; Nuthalapaty, S.; Vasu, K. K.; Sudarsanam, V. Eur. J. Med. Chem. 2010, 45, 3558-3563
8. Liu, J.; Ali, S. M.; Ashwell, M. A.; Ye, P.; Guan, Y.; Ng, S.-C.; Palma, R.; Yohannes, D. Preparation of quinazolinone derivatives useful in treatment of proliferative diseases and cancer. PCT Int. Appl. WO 2009002808 A2, 31 Dec 2008
9. Chem. Abstr. 2009, 150, 98369.
10. Chiu, G.; Gluchowski, C. Aromatic amine derivatives, preparation thereof, and their use for treatment of benign prostatic hyperplasia, lowering intraocular pressure, and inhibiting cholesterol synthesis. PCT Int. Appl. 1995, WO 9507075 A1, 19950316.
11. Gluchowski, C.; Forray, C. C.; Chiu, G.; Branchek, T. A.; Wetzel, J. M.; Hartig, P. R. Use of a1C-adrenergic receptor-specific compounds to treat benign prostatic hyperplasia. PCT Int. Appl. WO 9528157 A1, 1995, 19951026.
12. Chiu, G.; Gluchowski, C. Aromatic amine derivatives as selective α1C adrenergic antagonists useful for the treatment of benign prostatic hyperplasia. US 5508306 A, 1996, 19960416.
13. Roopashree, B.; Gayathri, V.; Gopi, A.; Devaraju, K. S. J. Coord. Chem. 2012, 65, 4023-4040
14. Taher, A. T.; Khalil, N. A.; Ahmed, E. M.; Ragab, Y. M. Chem. Pharm. Bull. 2012, 60, 778-784
15. Wang, X.-J.; Chu, N.-Y.; Wang, Q.-H.; Liu, C.; Jiang, C.-G; Wang, X.-Y.; Ikejima, T.; Cheng, M.-S. Bioorg. Med. Chem. Lett. 2012, 22, 6297-6300
16. El-Nassan, H. B. Eur. J. Med. Chem. 2012, 53, 22-27
17. Lu, Y.; Ou, Z.; Hu, W.; Le, X. Huaxue Xuebao 2012, 70, 973-979
18. Gowda, J.; Khader, A. M. A.; Kalluraya, B.; Hidayathulla, S. Indian J. Chem. Sect. B 2011, 50B, 1491-1495
19. Murray, J. M.; Sweeney, Z. K.; Chan, B. K.; Balazs, M.; Bradley, E.; Castanedo, G.; Chabot, C.; Chantry, D.; Flagella, M.; Goldstein, D. M. J. Med. Chem. 2012, 55, 7686-7695
20. Dale, A. G.; Hinds, J.; Mann, J.; Taylor, P. W.; Neidle, S. Biochemistry 2012, 51, 5860-5871
21. Steinijans, V. W.; Huber, R.; Hartmann, M.; Zech, K.; Bliesath, H.; Wurst, W.; Radtke, H. W. Int. J. Clin. Pharmacol., Ther. 1996, 34, 243-262
22. Lunn, W. H. W.; Harper, R. W.; Stone, R. L. J. Med. Chem. 1971, 14, 1069-1071
23. Dalla Via, L.; Gia, O.; Marciani Magno, S.; Da Settimo, A.; Marini, A. M.; Primofiore, G.; Da Settimo, F.; Salerno, S. Farmaco 2001, 56, 159-162
24. Yang, D.; Wang, Y.; Yang, H.; Liu, T.; Fu, H. Adv. Synth. Catal. 2012, 354, 477-482
25. Xu, H.; Fu, H. Chem.-Eur. J. 2012, 18, 1180-1186
26. Zhao, X.-H.; Liu, C.-J.; Li, Y.-P. Gaodeng Xuexiao Huaxue Xuebao 2010, 31, 1769-1773
27. Zhao, X.; Shi, D.-Q. J. Heterocycl. Chem. 2010, 47, 524-527
28. Shaabani, A.; Rahmati, A.; Farhangi, E.; Rezayan, A. H. Monatsh. Chem. 2007, 138, 615-618
29. Shaabani, A.; Farhangi, E.; Rahmati, A. Comb. Chem. High Throughput Screening 2006, 9, 771-776
30. Carpenter, R. D.; Lam, K. S.; Kurth, M. J. J. Org. Chem. 2007, 72, 284-287
31. Insuasty, B.; Salcedo, A.; Quiroga, J.; Abonia, R.; Nogueras, M.; Cobo, J.; Salido, S. Heterocycl. Commun. 2004, 10, 399-404
32. Bahekar, R. H.; Rao, A. R. R. Indian J. Heterocycl. Chem. 1999, 8, 225-228
33. Lunn, W. H. W.; Harper, R. W. Tetrahedron 1971, 27, 2079-2083
34. Schwaiger, J.; Becker, H. PCT Int. Appl. 2012045384, 12 Apr 2012.
35. Nosova, E. V.; Lipunova, G. N.; Laeva, A. A.; Charushin, V. N. Russ. J. Org. Chem. 2005, 41, 1671-1677
36. da Settimo, A.; Primofiore, G.; da Settimo, F.; Pardi, G.; Simorini, F.; Marini, A. M. J. Heterocycl. Chem. 2002, 39, 1007-1011
37. Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803-3805
38. Xiong, X. D.; Jiang, Y. W.; Ma, D. W. Org. Lett. 2012, 14, 2552-2555
39. Ma, D. W.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453-2455
40. Xie, X. A.; Cai, G. R.; Ma, D. W. Org. Lett. 2005, 7, 4693-4695
41. Li, L.; Wang, M.; Zhang, X. J.; Jiang, Y. W.; Ma, D. W. Org. Lett. 2009, 11, 1309-1312
42. Wang, Y.; Chi, Y.; Zhang, W. X.; Xi, Z. F. J. Am. Chem. Soc. 2012, 134, 2926-2929
43. Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C. G.; Huang, H. M. J. Am. Chem. Soc. 2012, 134, 20613-20616
44. Trost, B. M.; Osipov, M.; Dong, G. B. J. Am. Chem. Soc. 2010, 132, 15800-15807
45. Liu, C. R.; Wang, T. T.; Qi, Q. B.; Tian, S. K. Chem. Commn. 2012, 48, 10913-10915
46. Hao, W.; Geng, W. Z.; Zhang, W. X.; Xi, Z. F. Chem.-Eur. J. 2014, 20, 2605-2612
47. Chen, D. S.; Dou, G. L.; Li, Y. L.; Liu, Y.; Wang, X. S. J. Org. Chem. 2013, 78, 5700-5704
48. Yang, T.; Lin, C.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2005, 7, 4781-4784
49. Ma, D. W.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460
50. Ma, D. W.; Geng, Q.; Zhang, H.; Jiang, Y. W. Angew. Chem., Int. Ed. 2010, 49, 1291-1294