Acid-catalyzed addition of indoles to hydroxyquinones

Tetrahedron

Volumn 61, Issue 46, 2005, Pages 10894-10902

  Koulouri, Sofia ^a   Malamidou Xenikaki, Elizabeth ^a   Spyroudis, Spyros ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Acid catalysis; Hydroxyquinones; Indoles

Indexed keywords

2 HYDROXY 1,4 TRIPTYCENEQUINONE; 2 HYDROXY 5 METHYL 1,4 BENZOQUINONE; 2 HYDROXY 5 PHENYL 1,4 BENZOQUINONE; 2 HYDROXY 5,6 DIMETHYL 1,4 BENZOQUINONE; INDOLE; LAWSONE; QUINONE DERIVATIVE; RESORCINOL; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 26844563741     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.003     Document Type: Article

References (21)

1. R.H. Thomson Naturally occurring quinones IV 1997 Blackie Academic & Professional London
2. S. Spyroudis Molecules 5 2000 1291 1330
3. M. Tišler A.R. Katrizky Advances in heterocyclic chemistry Vol. 45 1989 Academic London 37
4. K. Liu, L. Xu, D. Szalkowski, Z. Li, V. Ding, G. Kwei, S. Huskey, D.E. Moller, J.V. Heck, B.B. Zhang, and A.B. Jones J. Med. Chem. 43 2000 3487 3494
5. J.-C. Henrion, B. Jacquet, M. Hocquaux, C. Lion, and M. Hedayatullah Bull. Soc. Chim. Belg. 105 1996 403 407
6. J.S. Yadav, B.V.S. Reddy, and T. Swamy Tetrahedron Lett. 44 2003 9121 9124
7. J.S. Yadav, B.V.S. Reddy, and T. Swamy Synthesis 2004 106 110
8. M.C. Pirrung, K. Park, and Z. Li Org. Lett. 3 2001 365 367
9. M.C. Pirrung, Z. Li, K. Park, and J. Zhu J. Org. Chem. 67 2002 7919 7926
10. M.C. Pirrung, L. Deng, Z. Li, and K. Park J. Org. Chem. 67 2002 8374 8378
11. O. Ottoni, A. Neder, F. deV, A.K.B. Dias, R.P.A. Cruz, and L.B. Aquino Org. Lett. 3 2001 1005 1007
12. N. Tajima, T. Hayashi, and S.-i. Nakatsuka Tetrahedron Lett. 41 2001 1059 1062
13. J.S. Yadav, B.V. Subba Reddy, Ch.V.S.R. Murthy, G. Majesh Kumar, and Ch. Madan Synthesis 2001 783 787
14. C. Lion, J.-C. Henrion, B. Jacquet, M. Hocquaux, J. Maignan, G. Barre, and R. Baudry Bull. Soc. Chim. Belg. 106 1997 835 836
15. H. Itokawa, Y. Qiao, and K. Takeya Phytochemistry 30 1991 637 640
16. E. Malamidou-Xenikaki, S. Spyroudis, and M. Tsanakopoulou J. Org. Chem. 68 2003 5627 5631
17. L.F. Fieser, and M.L. Ardao J. Am. Chem. Soc. 78 1956 774 781
18. S. Spyroudis, and N. Xanthopoulou J. Org. Chem. 67 2002 4612 4614
19. R.B. Woodward, F. Sondheimer, D. Toup, K. Heusler, and W.M. McLamore J. Am. Chem. Soc. 74 1952 4223 4251
20. L. Fieser J. Am. Chem. Soc. 70 1948 3165 3173
21. L. Fieser J. Am. Chem. Soc. 48 1926 2922 2937