CuCl2-promoted 6- endo-dig chlorocyclization and oxidative aromatization cascade: Efficient construction of 1-azaanthraquinones from N -propargylaminoquinones

Organic Letters

Volumn 13, Issue 16, 2011, Pages 4208-4211

  Fei, Na ^a   Yin, Hao ^a   Wang, Shaozhong ^a   Wang, Huaqin ^a   Yao, Zhu Jun ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOQUINOLINE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; COPPER; CUPRIC CHLORIDE; HETEROCYCLIC COMPOUND; PROPANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

AMINOQUINOLINES; ANTHRAQUINONES; AZA COMPOUNDS; COPPER; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROPANE;

EID: 80051699216     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201542h     Document Type: Article

References (25)

1. Chaves, M. H.; Santos, L. A.; Lago, J. H. G.; Roque, N. F. J. Nat. Prod. 2001, 64, 240
2. Molinski, T. F. Chem. Rev. 1993, 93, 1825
3. Marshall, K. M.; Barrows, L. R. Nat. Prod. Rep. 2004, 21, 731
4. Pautet, F.; Nebois, P.; Bouaziz, Z.; Fillion, H. Heterocycles 2001, 54, 1095
5. Lazny, R.; Nodzewska, A. Chem. Rev. 2010, 110, 1386
6. Jiang, C.; Xu, M.; Wang, S.; Wang, H.; Yao, Z.-J. J. Org. Chem. 2010, 75, 4323
7. Fei, N.; Hou, Q.; Wang, S.; Wang, H.; Yao, Z.-J. Org. Biomol. Chem. 2010, 8, 4096
8. For a review on naturally occurring organohalogen compounds, see: Gribble, G. W. Acc. Chem. Res. 1998, 31, 141
9. Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245
10. Zhu, G.; Ma, S.; Lu, X.; Huang, Q. Chem. Commun. 1995, 271
11. Lee, C.-Y.; Wu, M.-J. Eur. J. Org. Chem. 2007, 3463
12. Yin, G.; Liu, G. Angew. Chem., Int. Ed. 2008, 47, 5442
13. Ye, S.; Gao, K.; Zhou, H.; Yang, X.; Wu, J. Chem. Commun. 2009, 5406
14. Li, Y.; Jardine, K. J.; Tan, R.; Song, D.; Dong, V. M. Angew. Chem., Int. Ed. 2009, 48, 784
15. For an account on chloropalladation, see: Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115
16. Ma, S. Acc. Chem. Res. 2003, 36, 701
17. Jithunsa, M.; Ueda, M.; Miyata, O. Org. Lett. 2011, 13, 518
18. Liang, Y.; Xie, Y.-X.; Li, J.-H. Synthesis 2007, 400
19. Hashmi, A. S. K.; Schuster, A. M.; Zimmer, M.; Rominger, F. Chem.-Eur. J. 2011, 17, 5511
20. Shen, Z.; Lu, X. Adv. Synth. Catal. 2009, 351, 3107
21. Chen, C.-C.; Chin, L.-Y.; Yang, S.-C.; Wu, M.-J. Org. Lett. 2010, 12, 5652
22. Yu, X.; Wu, J. J. Comb. Chem. 2009, 11, 895
23. CCDC 780630 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www. Ccdc.cam.ac.uk/data-request/cif.
24. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068
25. Castitas, A.; King, A. E.; Parella, T.; Costas, M.; Stahl, S. S.; Ribas, X. Chem. Sci. 2010, 1, 326