Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation

Synlett

Volumn , Issue 6, 2005, Pages 1003-1005

  Robinson, Ross S ^a,b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

hydroxy ketones; Direct conversion; Quinoxalines

Indexed keywords

ALPHA HYDROXY KETONE DERIVATIVE; KETOL; KETONE DERIVATIVE; METAL; PALLADIUM; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; OXIDATION; SCREENING; SYNTHESIS;

EID: 17144375635     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-864830     Document Type: Article

References (18)

1. (a) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788.
2. (b) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Chem. Commun. 2003, 2286.
3. Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198.
4. For reviews see: (a) Sakata, G.; Makino, K.; Kurasawa, Y. Heterocycles 1988, 27, 2481.
5. (b) Sato, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier Science Ltd.: Oxford, 1996, Vol. 6, Chap. 6.03.
6. For more recent references see: (a) Aguirre, G.; Cerecetto, H.; Di Maio, R.; González, M.; Alfaro, M. E. M.; Jaso, A.; Zarranz, B.; Onega, M. A.; Aldana, I.; Monge-Vega, A. Bioorg. Med. Chem. Lett. 2004, 14, 3835.
7. (b) Zarranz, B.; Jaso, A.; Aldana, I.; Monge, A. Bioorg. Med. Chem. 2004, 12, 3711.
8. (c) Kim, J. H.; Kim, J. H.; Lee, G. E.; Kim, S. W.; Chung, I. K. Biochem. J. 2003, 373, 523.
9. (d) Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2002, 45, 5604.
10. For recent reviews see: (a) Zhan, B.-Z.; Thompson, A. Tetrahedron 2004, 60, 2917.
11. (b) Muzart, J. Tetrahedron 2003, 59, 5789.
12. Lee, M.; Chang, S. Tetrahedron Lett. 2000, 41, 7507.
13. Dijksman, A.; Marino-González, A.; Payeras, A. M.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826.
14. (a) Schultz, M. J.; Park, C. C.; Sigman, M. S. Chem. Commun. 2002, 3034.
15. (b) See also: Mueller, J. A.; Goller, C. P.; Sigman, M. S. J. Am. Chem. Soc. 2004, 126, 9725.
16. 11a) mp 79-80 °C); spectroscopic data consistent with those published (ref. 10b).
17. (a) Ihmels, H.; Maggini, M.; Prato, M.; Scorrano, G. Tetrahedron Lett. 1991, 32, 6215.
18. (b) Fürstner, A.; Leitner, A.; Méndez, M.; Jrause, H. J. Am. Chem. Soc. 2002, 124, 13856.