Copper-catalyzed synthesis of quinoxalines with o-phenylenediamine and terminal alkyne in the presence of bases

Organic Letters

Volumn 13, Issue 17, 2011, Pages 4514-4517

  Wang, Wen ^a,b   Shen, Yongwen ^a,b   Meng, Xu ^a,b   Zhao, Mingming ^a,b   Chen, Yongxin ^a,b   Chen, Baohua ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b Key Laboratory of Nonferrous Metal Chemistry   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 PHENYLENEDIAMINE; 1,2-DIAMINOBENZENE; ALKYNE; CARBONIC ACID DERIVATIVE; CESIUM; CESIUM CARBONATE; COPPER; ORGANOMETALLIC COMPOUND; PHENYLENEDIAMINE DERIVATIVE; QUINOXALINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; CARBONATES; CATALYSIS; CESIUM; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHENYLENEDIAMINES; QUINOXALINES; STEREOISOMERISM;

EID: 80052241634     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201664x     Document Type: Article

References (23)

1. Dailey, S.; Feast, J. W.; Peace, R. J.; Sage, I. C.; Till, S.; Wood, E. L. J. Mater.Chem. 2001, 11, 2238
2. Brock, E. D.; Lewis, D. M.; Yousaf, T. I.; Harper, H. H. The Procter and Gamble Co. WO9951688, 1999.
3. Sonawane, N. D.; Rangnekar, D. W. J. Heterocycl. Chem. 2002, 39, 303
4. Schutz, H. Benzodiazepines; Springer: Heidelberg, 1982.
5. Landquist, J. K. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 1, pp 166-170.
6. Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2002, 45, 5604
7. Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Bioorg. Med. Chem. Lett. 2004, 14, 541
8. He, W.; Meyers, M. R.; Hanney, B.; Spada, A.; Blider, G.; Galzeinski, H.; Amin, D.; Needle, S.; Page, K.; Jayyosi, Z.; Perrone, H. Bioorg. Med. Chem. Lett. 2003, 13, 3097
9. Lindsley, C. W.; Zhao, Z.; Leister, W. H.; Robinson, R. G.; Barnett, S. F.; Defeo- Jones, D.; Jones, R. E.; Hartman, G. D.; Huff, J. R.; Huber, H. E.; Duggan, M. E. Bioorg. Med. Chem. Lett. 2005, 15, 761
10. Porter, A. E. A. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; p 157.
11. Woo, G. H. C.; Snyder, J. K.; Wan, Z. K. Prog. Heterocycl Chem. 2002, 14, 279
12. Katritzky, A. R.; Zhang, D.; Kirichenko., K. J. Org. Chem. 2005, 70, 3271
13. Merkul, E.; Dohe, J.; Gers, C.; Rominger, F.; Muller, T. J. J. Angew. Chem., Int. Ed. 2011, 50, 2966
14. Mousset, C.; Provot, O.; Hamze, A.; Brion, J.-D.; Alami, M. Tetrahedron 2008, 64, 4287
15. Chandrasekhar, S.; Kesava Reddy, N.; Praveen Kumar., V. Tetrahedron Lett. 2010, 51, 3623
16. Deng, X.; Mani, N. S. Org. Lett. 2006, 8, 269
17. Rogatchov, V. O.; Filimonov, V. D.; Yusubov, M. S. Synthesis 2001, 1001
18. Bhosale, R. S.; Sarda, S. R.; Ardhapure, S. S.; Jadhav, W. N.; Bhusare, S. R.; Pawar, R. P. Tetrahedron Lett. 2005, 46, 7183
19. Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28
20. Cai, J.; Zou, J. P.; Pan, X. Q.; Zhang, W. Tetrahedron Lett. 2008, 49, 7386
21. Zhou, L.; Shi, Y.; Xiao, Q,; Liu, Y. z.; Ye, F.; Zhang, Y.; Wang, J. B. Org. Lett. 2011, 13, 968
22. Tetsuya Hamada, Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833
23. Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 1114