A novel ruthenium-catalyzed dehydrogenative synthesis of 2-arylquinazolines from 2-aminoaryl methanols and benzonitriles

Organic Letters

Volumn 16, Issue 22, 2014, Pages 6028-6031

  Chen, Mengmeng ^a,b   Zhang, Min ^a   Xiong, Biao ^a   Tan, Zhenda ^a   Lv, Wan ^a   Jiang, Huanfeng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b JIANGNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84912544490     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503052s     Document Type: Article

References (57)

1. Parhi, A. K.; Zhang, Y.; Saionz, K. W.; Pradhan, P.; Kaul, M.; Trivedi, K.; Pilch, D. S.; LaVoie, E. J. Bioorg. Med. Chem. Lett. 2013, 23, 4968
2. Chien, T.-C.; Chen, C.-S.; Yu, F.-H.; Chern, J.-W. Chem. Pharm. Bull. 2004, 52, 1422
3. Ugale, V. G.; Bari, S. B. Eur. J. Med. Chem. 2014, 80, 447
4. Juvale, K.; Gallus, J.; Wiese, W. Bioorg. Med. Chem. 2013, 21, 7858
5. Ple, P. A.; Green, T. P.; Hennequin, L. F.; Curwen, J.; Fennell, M.; Allen, J.; Lambertvan der Brempt, C.; Costello, G. J. Med. Chem. 2004, 47, 871
6. Zhao, D.; Shen, Q.; Zhou, Y. R.; Li, J. X. Org. Biomol. Chem. 2013, 11, 5908
7. Zhang, Y. L.; Sheets, M. R.; Raja, E. K.; Boblak, K. N.; Klumpp, D. A. J. Am. Chem. Soc. 2011, 133, 8467
8. Fang, J.; Zhou, J. G.; Fang, Z. J. RSC Adv. 2013, 3, 334
9. Han, B.; Yang, X. L.; Wang, C.; Bai, Y. W.; Pan, T. C.; Chen, X.; Yu, W. J. Org. Chem. 2012, 77, 1136
10. Yuan, H.; Yoo, W. J.; Miyamura, H.; Kobayashi, S. Adv. Synth. Catal. 2012, 354, 2899
11. Maheswari, C. U.; Kumar, G. S.; Venkateshwar, M.; Kumar, R. A.; Kantam, M. L.; Reddy, K. R. Adv. Synth. Catal. 2010, 352, 341
12. Han, B.; Wang, C.; Han, R. F.; Yu, W.; Duan, X. Y.; Fang, R.; Yang, X. L. Chem. Commun. 2011, 47, 7818
13. Zhang, J. T.; Yu, C. M.; Wang, S. J.; Wan, C. F.; Wang, Z. Y. Chem. Commun. 2010, 46, 5244
14. Yan, Y. Z.; Zhang, Y. H.; Feng, C. T.; Zha, Z. G.; Wang, Z. Y. Angew. Chem., Int. Ed. 2012, 51, 8077
15. Panja, S. K.; Saha, S. RSC Adv. 2013, 3, 14495
16. Panja, S. K.; Dwivedi, N.; Saha, S. Tetrahedron Lett. 2012, 53, 6167
17. Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. Chem. Commun. 2008, 2935
18. Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. J. Org. Chem. 2009, 74, 4934
19. Alonso, R.; Caballero, A.; Campos, P. J.; Sampedro, D.; Rodríguez, M. A. Tetrahedron 2010, 66, 4469
20. Chen, Y. C.; Yang, D. Y. Tetrahedron 2013, 69, 10438
21. Ju, J.; Hua, R. M.; Su, J. Tetrahedron 2012, 68, 9364
22. Truong, V. L.; Morrow, M. Tetrahedron Lett. 2010, 51, 758
23. Malakar, C. C.; Baskakova, A.; Conrad, J.; Beifuss, U. Chem.-Eur. J. 2012, 18, 8882
24. Omar, M. A.; Conrad, J.; Beifuss, U. Tetrahedron 2014, 70, 5682
25. Omar, M. A.; Conrad, J.; Beifuss, U. Tetrahedron 2014, 70, 3061
26. Zhang, W.; Guo, F.; Wang, F.; Zhao, N.; Liu, L.; Li, J.; Wang, Z. H. Org. Biomol. Chem. 2014, 12, 5752
27. Ohta, Y.; Tokimizu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2010, 12, 3963
28. Lin, J. P.; Zhang, F. H.; Long, Y. Q. Org. Lett. 2014, 16, 2822
29. Chen, M. M.; Zhang, M.; Xie, F.; Wang, X. T.; Jiang, H. F. ChemCatChem 2014, 6, 2993
30. Xie, F.; Zhang, M.; Jiang, H. F.; Chen, M. M.; Lv, W.; Zhen, A. B.; Jian, X. J. Green Chem. 2014, DOI: 10.1039/C4GC01316F.
31. Xie, F.; Chen, M.-M.; Wang, X.-T.; Jiang, H.-F.; Zhang, M. Org. Biomol. Chem. 2014, 12, 2761
32. Wang, X. T.; Chen, M. M.; Xie, F.; Zhang, M. RSC Adv. 2014, 4, 14744
33. Xie, F.; Yan, F. X.; Chen, M. M.; Zhang, M. RSC Adv. 2014, 4, 29502
34. Zhang, M.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 597
35. Zhang, M.; Fang, X.; Neumann, H.; Beller, M. J. Am. Chem. Soc. 2013, 135, 11384
36. Xie, F.; Wang, X. T.; Yan, F. X.; Wang, T.; Chen, M. M.; Ding, Y. Q. RSC Adv. 2013, 3, 6022
37. Zhang, M.; Imm, S.; Bahn, S.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 11197
38. Khusnutdinova, J. R.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2014, 136, 2998
39. Hille, T.; Irrgang, T.; Kempe, R. Chem.-Eur. J. 2014, 20, 5569
40. Michlik, S.; Kempe, R. Nat. Chem. 2013, 140
41. Gunanathan, C.; Milstein, D. Science 2013, 249
42. Balaraman, E.; Khaskin, E.; Leitus, G.; Milstein, D. Nat. Chem. 2013, 5, 122
43. Srimani, D.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2013, 52, 4012
44. Srimani, D.; Ben-David, Y.; Milstein, D. Chem. Commun. 2013, 49, 6632
45. Srimani, D.; Balaraman, E.; Hu, P.; Ben-David, Y.; Milstein, D. Adv. Synth. Catal. 2013, 355, 2525
46. Prechtl, M. H. G.; Wobser, K.; Theyssen, N.; Ben-David, Y.; Milstein, D.; Leitner, W. Catal. Sci. Technol. 2012, 2, 2039
47. Kossoy, E.; Diskin-Posner, Y.; Leitus, G.; Milstein, D. Adv. Synth. Catal. 2012, 354, 497
48. Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468
49. Gnanaprakasam, B.; Ben-David, Y.; Milstein, D. Adv. Synth. Catal. 2012, 354, 2403
50. Gnanaprakasam, B.; Ben-David, Y.; Milstein, D. Adv. Synth. Catal. 2010, 352, 3169
51. Dong, J.-X.; Long, Z.; Song, F.-J.; Wu, N. J.; Guo, Q.; Lan, J.-B.; You, J.-S. Angew. Chem., Int. Ed. 2013, 52, 580
52. Ding, S.-T.; Jiao, N. J. Am. Chem. Soc. 2011, 133, 12374
53. Wang, Z.; Li, K.-Z.; Zhao, D.-B.; Lan, J.-B.; You, J.-S. Angew. Chem., Int. Ed. 2011, 50, 5365
54. Pena, B.; David, A.; Pavani, C.; Baptista, M. S.; Pellois, J.-P.; Turro, C.; Dunbar, K. R. Organometallics 2014, 33, 1100
55. Barnard, J. H.; Wang, C.; Berry, N. G.; Xiao, J. Chem. Sci. 2013, 4, 1234
56. Dong, Y. P.; Shi, M. J.; Tong, B. H.; Zhang, Q. F. Luminescence 2012, 27, 414
57. Yang, W.; Fu, H.; Song, Q.; Zhang, M.; Ding, Y. Organometallics 2011, 30, 77