Cascade couplings of N -alkyl- N -methacryloyl benzamides with ethers and benzenesulfonohydrazides to generate isoquinoline-1,3(2 H,4 H)-dione derivatives

Journal of Organic Chemistry

Volumn 80, Issue 8, 2015, Pages 4176-4183

  Zhang, Min ^a   Xie, Ping ^a   Zhao, Wannian ^a   Niu, Ben ^a   Wu, Wei ^a   Bian, Zhaogang ^a   Pittman, Charles U ^b   Zhou, Aihua ^a  

^a JIANGSU UNIVERSITY   (China)

^b MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLINGS;

AROMATIC RINGS; BENZAMIDES; DRUG DISCOVERY; FUNCTIONALIZATIONS; FUNCTIONALIZED; ISOQUINOLINES; RADICAL CYCLIZATIONS;

ETHERS;

2 ETHYL 4 METHYL 4 (TOSYLMETHYL)ISOQUINOLINE 1,3 (2H,4H)DIONE; 2 ETHYL 4 METHYL 4 [(PHENYLSULFONYL)METHYL]ISOQUINOLINE 1,3 (2H,4H)DIONE; 2 ETHYL 4 METHYL 4 [(TETRAHYDROFURAN 2 YL)METHYL]ISOQUINOLINE 1,3 (2H,4H)DIONE; 2 ISOPROPYL 4 METHYL 4 (TOSYLMETHYL)ISOQUINOLINE 1,3 (2H,4H)DIONE; 2 ISOPROPYL 4 METHYL 4 [(PHENYLSULFONYL)METHYL]ISOQUINOLINE 1,3 (2H,4H)DIONE; 2 ISOPROPYL 4 METHYL 4 [(TETRAHYDROFURAN 2 YL)METHYL]ISOQUINOLINE 1,3 (2H,4H)DIONE; 2,4 DIMETHYL 4 (TOSYLMETHYL)ISOQUINOLINE 1,3 (2H,4H)DIONE; 2,4 DIMETHYL 4 [(PHENYLSULFONYL)METHYL]ISOQUINOLINE 1,3 (2H,4H)DIONE; 4 (2 ETHOXYPROPYL) 2 ISOPROPYL 4 METHYLISOQUINOLINE 1,3 (2H,4H)DIONE; 4 [(1,4 DIOXAN 2 YL)METHYL] 2 ETHYL 4 METHYLISOQUINOLINE 1,3 (2H,4H)DIONE; 4 [(1,4 DIOXAN 2 YL)METHYL] 2,4 DIMETHYLISOQUINOLINE 1,3 (2H,4H)DIONE; BENZAMIDE DERIVATIVE; BENZENESULFONOHYDRAZIDE; ETHER DERIVATIVE; HYDRAZIDE DERIVATIVE; ISOQUINOLINE DERIVATIVE; N ALKYL N METHACRYLOYL BENZAMIDE; UNCLASSIFIED DRUG; 1,3(2H,4H)-ISOQUINOLINEDIONE; METHACRYLIC ACID DERIVATIVE;

ARTICLE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; CHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BENZAMIDES; CYCLIZATION; ETHERS; ISOQUINOLINES; METHACRYLATES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84928143311     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00158     Document Type: Article

References (52)

1. Mortier, J.; Masereel, B.; Remouchamps, C.; Ganeff, C.; Piette, J.; Frederick, R. Bioorg. Med. Chem. Lett. 2010, 20, 4515-4520
2. Mayer, S. C.; Banker, A. L. F.; Boschelli, L. D.; Johnson, M.; Kenny, C. H.; Krishnamurthy, G.; Kutterer, K.; Moy, F. Bioorg. Med. Chem. Lett. 2008, 18, 3641-3645
3. Chen, Y. H.; Zhang, Y. H.; Zhang, H. J.; Liu, D. Z.; Gu, M.; Li, J. Y.; Wu, F.; Zhu, X. Z.; Li, J.; Nan, F. J. J. Med. Chem. 2006, 49, 1613-1623
4. Zhang, L.; Zheng, M.; Zhao, F.; Zhai, Y.; Liu, H. ACS Comb. Sci. 2014, 16 (4) 184-191
5. Ji, T.; Wang, Y.; Wang, M.; Niu, B.; Xie, P.; Pittman, C. U., Jr.; Zhou, A. ACS Comb. Sci. 2013, 15 (12) 595-600
6. Noguchi, T.; Sano, H.; Shimazawa, R.; Tanatani, A.; Miyachi, H.; Hashimoto, Y. Bioorg. Med. Chem. Lett. 2004, 14, 4141-4145
7. Billamboz, M.; Bailly, F.; Lion, C.; Touati, N.; Vezin, H.; Calmels, C.; Andreola, M. L.; Christ, F.; Debyser, Z.; Cotelle, P. J. Med. Chem. 2011, 54, 1812-1824
8. Zou, J. W.; Luo, C. C.; Zhang, H. X.; Liu, H. C.; Jiang, Y. J.; Yu, Q. S. J. Mol. Graphics Modell. 2007, 26, 494-504
9. Miyachi, H.; Kato, M.; Kato, F.; Hashimoto, Y. J. Med. Chem. 1998, 41, 263-265
10. Komoda, M.; Kakuta, H.; Takahashi, H.; Fujimoto, Y.; Kadoya, S.; Kato, F.; Hashimoto, Y. Bioorg. Med. Chem. 2001, 9, 121-131
11. Lu, X. Y.; Chen, Y. D.; Sun, N. Y.; Jiang, Y. J.; You, Q. D. J. Mol. Model. 2010, 16, 163-173
12. Campagnola, G.; Gong, P.; Peersen, O. B. Antiviral Res. 2011, 91, 241-251
13. Ma, T.; Chen, W. T.; Zhang, G. L.; Yu, Y. P. J. Comb. Chem. 2010, 12, 488-490
14. Nakagawa, A.; Uno, S.; Makishima, M.; Miyachi, H.; Hashimoto, Y. Bioorg. Med. Chem. 2008, 16, 7046-7054
15. Billamboz, M.; Suchaud, V.; Bailly, F.; Lion, C.; Demeulemeester, J.; Calmels, C.; Andréola, M.; Christ, F.; Debyser, Z.; Cotelle, P. ACS Med. Chem. Lett. 2013, 4 (7) 606-611
16. Billamboz, M.; Bailly, F.; Lion, C.; Touati, N.; Vezin, H.; Calmels, C.; Andréola, M.; Christ, F.; Debyser, Z.; Cotelle, P. J. Med. Chem. 2011, 54 (6) 1812-1824
17. Tsou, H.; Otteng, M.; Tran, T.; Floyd, M. B.; Reich, M., Jr.; Birnberg, G.; Kutterer, K.; Kaloustian, S. A.; Ravi, M.; Nilakantan, R.; Grillo, M.; McGinnis, J. P.; Rabindran, S. K. J. Med. Chem. 2008, 51 (12) 3507-3525
18. Chen, Y. H.; Zhang, Y. H.; Zhang, H. J.; Liu, D. Z.; Gu, M.; Li, J. Y.; Wu, F.; Zhu, X. Z.; Li, J.; Nan, F. J. J. Med. Chem. 2006, 49 (5) 1613-1623
19. Young, S. D.; Wiggins, J. M.; Huff, J. R. J. Org. Chem. 1988, 53, 1115-1116
20. Ozcan, S.; Dengiz, C.; Deliömeroglu, M. K.; Sahin, E.; Balci, M. Tetrahedron Lett. 2011, 52, 1495-1497
21. Pan, Y. J.; Holmes, C. P.; Tumelty, D. J. Org. Chem. 2005, 70, 4897-4900
22. Dongare, M. K.; Bhagwat, V. V.; Ramana, C. V.; Gurjar, M. K. Tetrahedron Lett. 2004, 45, 4759-4762
23. Vicente, J.; Pablo, G. H.; Roberto, F. P.; Chicote, M. T. Organometallics 2011, 30, 1079-1093
24. Béatrice, Q. S.; Zard, S. Z. Chem. Commun. 2002, 38, 2306-2307
25. Li, L.; Deng, M.; Zheng, S. C.; Xiong, Y. P.; Tan, B.; Liu, X. Y. Org. Lett. 2014, 16, 504-507
26. Kong, W. Q.; Casimiro, M.; Fuentes, N.; Merino, E.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 13086-13090
27. Xie, J.; Xu, P.; Li, H. M.; Xue, Q. C.; Jin, H. M.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2013, 49, 5672-5674
28. Wei, H. L.; Piou, T.; Four, J. D.; Neuville, L.; Zhu, J. P. Org. Lett. 2011, 13 (9) 2244-2247
29. Wei, W.; Wen, J. G.; Yang, D. S.; Liu, X. X.; Guo, M. Y.; Dong, R. M.; Wang, H. J. Org. Chem. 2014, 79, 4225-4230
30. Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985-7989
31. Meng, Y.; Guo, L. N.; Wang, H.; Duan, X. H. Chem. Commun. 2013, 49, 7540-7542
32. Gong, W.; Xu, L.; Ji, T.; Xie, P.; Qi, X.; Pittman, C. U., Jr.; Zhou, A. RSC Adv. 2014, 4, 6854-6857
33. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054-3131
34. Wasa, M.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 14058-14059
35. Wei, H. L.; Piou, T.; Dufour, J.; Neuville, L.; Zhu, J. P. Org. Lett. 2011, 13, 2244-2247
36. Tang, B. X.; Song, R. J.; Wu, C. Y.; Liu, Y.; Zhou, M. B.; Wei, W. T.; Deng, G. B.; Yin, D. L.; Li, J. H. J. Am. Chem. Soc. 2010, 132, 8900-8902
37. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748-8758
38. Jia, C. G.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633-639
39. Tian, Q. S.; He, P.; Kuang, Ch. X. Org. Biomol. Chem. 2014, 12, 6349-6353
40. Li, Z. J.; Zhang, Y.; Zhang, L. Z.; Liu, Z. Q. Org. Lett. 2014, 16, 382-385
41. Zhou, S. L.; Guo, L. N.; Wang, H.; Duan, X. H. Chem.-Eur. J. 2013, 19, 12970-12973
42. Zhou, S. L.; Guo, L. N.; Wang, S.; Duan, X. H. Chem. Commun. 2014, 50, 3589-3591
43. Wei, W. T.; Zhou, M. B.; Fan, J. H.; Liu, W.; Song, R. J.; Liu, Y.; Hu, M.; Xie, P.; Li, J. H. Angew. Chem., Int. Ed. 2013, 52, 3638-3641
44. Li, X. Q.; Xu, X. S.; Hu, P. Z.; Xiao, X. Q.; Zhou, C. J. Org. Chem. 2013, 78, 7343-7348
45. Wang, H.; Guo, L. N.; Duan, X. H. Org. Biomol. Chem. 2013, 11, 4573-4576
46. Zhao, J. C.; Fang, H.; Qian, P.; Han, J. L.; Pan, Y. Org. Lett. 2014, 16, 5342-5345
47. Yuan, Y. C.; Hou, W. J.; Negrerie, D. Z.; Zhao, K.; Du, Y. F. Org. Lett. 2014, 16, 5410-5413
48. Zhou, S. L.; Guo, L. N.; Wang, S.; Duan, X. H. Chem. Commun. 2014, 50, 3589-3591
49. Liu, Z. Q.; Sun, L.; Wang, J. G.; Han, J.; Zhao, Y. K.; Zhou, B. Org. Lett. 2009, 11, 1437-1439
50. Liu, Z. Q.; Zhao, L.; Shang, X.; Cui, Z. Org. Lett. 2012, 14, 3218-3221
51. Cui, Z.; Shang, X.; Shao, X. F.; Liu, Z. Q. Chem. Sci. 2012, 3, 2853-2858
52. Li, Z.; Fan, F.; Yang, J.; Liu, Z. Q. Org. Lett. 2014, 16, 3396-3399