Synthesis of 7-hydroxy-2-(2-hydroxybenzoyl)benzo[c]chromen-6-ones by sequential application of domino reactions of 1,3-bis(silyl enol ethers) with benzopyrylium triflates

Tetrahedron

Volumn 62, Issue 50, 2006, Pages 11755-11759

  Lubbe, Mathias ^a   Appel, Bettina ^b   Flemming, Anke ^a   Fischer, Christine ^c   Langer, Peter ^a,c  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

^c LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Chromones; Cyclizations; Domino reactions; Oxygen heterocycles; Silyl enol ethers

Indexed keywords

2,4 BIS(TRIMETHYLSILYLOXY)PENTA 1,3 DIENE; 7 HYDROXY 2 (2 HYDROXY 5 METHYLBENZOYL)BENZO[C]CHROMEN 6 ONE; 7 HYDROXY 2 (2 HYDROXYBENZOYL) 8 (METHYL)BENZO[C]CHROMEN 6 ONE; 7 HYDROXY 2 (2 HYDROXYBENZOYL)BENZO[C]CHROMEN 6 ONE; 7 HYDROXY 2 (5 CHLORO 2 HYDROXYBENZOYL)BENZO[C]CHROMEN 6 ONE; 8 ETHYL 7 HYDROXY 2 (2 HYDROXYBENZOYL)BENZO[C]CHROMEN 6 ONE; BENZOPYRAN DERIVATIVE; CHROMENE DERIVATIVE; CHROMONE DERIVATIVE; PHENOL DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DRUG SYNTHESIS; LACTONIZATION; MICHAEL ADDITION; POLYMERIZATION; PRIORITY JOURNAL;

EID: 33750617155     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.029     Document Type: Article

References (24)

1. Sidwell W.T.L., Fritz H., and Tamm C. Helv. Chim. Acta 54 (1971) 207
2. Tamm C. Arzneim.-Forsch. 22 (1972) 1776
3. Raistrick H., Stilkings C.E., and Thomas R. Biochemistry 55 (1953) 421
4. Pero R.W., Harvan D., and Blois M.C. Tetrahedron Lett. 14 (1973) 945
5. Schmidt J.M., Tremblay G.B., Page M., Mercure J., Feher M., Dunn-Dufault R., Peter M.G., and Redden P.R. J. Med. Chem. 46 (2003) 1289
6. Pandey J., Jha A.K., and Hajela K. Bioorg. Med. Chem. 12 (2004) 2239
7. McGee L.R., and Confalone P.N. J. Org. Chem. 53 (1988) 3695
8. Hart D.J., and Mannino A. Tetrahedron 52 (1996) 3841
9. Fischer C., Lipata F., and Rohr J. J. Am. Chem. Soc. 125 (2003) 7818 and references cited therein
10. Sayer J.M., Haruhiko Y., Wood A.W., Conney A.H., and Jerina D.M. J. Am. Chem. Soc. 104 (1982) 5562
11. Geevanada Y.A., Gunawardana P., Kumar N.S., and Sultanbawa M.U.S. Phytochemistry 18 (1979) 1017
12. For salicylic esters and salicylic glycosides (e.g., salicortin), see for example:. In: Steglich W., Fugmann B., and Lang-Fugmann S. (Eds). Römpp Lexikon Naturstoffe (1997), Thieme, Stuttgart
13. Pettit G.R., Toki B., Herald D.L., Verdier-Pinard P., Boyd M.R., Hamel E., and Pettit R.K. J. Med. Chem. 41 (1998) 1688
14. Liou J.-P., Chang J.-Y., Chang C.-W., Chang C.-Y., Mahindroo N., Kuo F.-M., and Hsieh H.-P. J. Med. Chem. 47 (2004) 2897
15. Liou J.-P., Chang C.-W., Song J.S., Yang Y.S., Yeh C.F., Tseng H.Y., Lo Y.K., Chang C.-L., Chang C.-M., and Hsieh H.-P. J. Med. Chem. 45 (2002) 2556
16. For a review of 1,3-bis(silyl enol ethers), see:. Langer P. Synthesis (2002) 441
17. Langer P., and Appel B. Tetrahedron Lett. 44 (2003) 7921
18. Nguyen V.T.H., Appel B., and Langer P. Tetrahedron 62 (2006) 7674
19. Appel B., Rotzoll S., Kranich R., Reinke H., and Langer P. Eur. J. Org. Chem. (2006) 3638
20. Langer P., Saleh N.N.R., and Freifeld I. Chem. Commun. (2002) 168
21. Appel B., Saleh N.N.R., and Langer P. Chem.-Eur. J. 12 (2006) 1221
22. Ullah E., Appel B., Fischer C., and Langer P. Tetrahedron 62 (2006) 9694
23. Banyopadhyay C., Sur K.R., and Patra R. J. Chem. Res., Synop. 12 (1998) 802
24. Jean J.C., Wise L.D., Heffner T.G., Pugsley T.A., and Meltzer L.T. J. Med. Chem. 34 (1991) 248