Application of Baylis-Hillman methodology in the synthesis of coumarin derivatives

Synthetic Communications

Volumn 33, Issue 10, 2003, Pages 1755-1770

  Kaye, Perry T ^a   Musa, M A ^a  

^a RHODES UNIVERSITY   (South Africa)

Author keywords

Baylis Hillman reaction; Coumarins; Synthesis

Indexed keywords

2 BENZYLOXY 5 CHLOROBENZALDEHYDE; ANTIBIOTIC AGENT; ANTIRETROVIRUS AGENT; BENZYLAMINE DERIVATIVE; CALANOLIDE A; CALANOLIDE B; CLOROBIOCIN; COUMARIN DERIVATIVE; DICOUMAROL; ESTER; METHYL 2 (BENZYLAMINOMETHYL) 3 (2 BENZYLOXY 3 ETHOXYPHENYL) 3 HYDROXYPROPANOATE; METHYL 2 (BENZYLAMINOMETHYL) 3 (2 BENZYLOXY 3 METHOXYPHENYL) 3 HYDROXYPROPANOATE; METHYL 2 (BENZYLAMINOMETHYL) 3 (2 BENZYLOXY 3,5 DIBROMOMETHYL) 3 HYDROXYPROPANOATE; METHYL 2 (BENZYLAMINOMETHYL) 3 (2 BENZYLOXY 5 BROMOPHENYL) 3 HYDROXYPROPANOATE; METHYL 2 (BENZYLAMINOMETHYL) 3 (2 BENZYLOXY 5 CHLOROPHENYL) 3 HYDROXYPROPANOATE; METHYL 2 (BENZYLAMINOMETHYL) 3 (2 BENZYLOXYPHENYL) 3 HYDROXYPROPANOATE; METHYL 3 (2 BENZYLOXY 3 CHLOROPHENYL) 3 HYDROXY 2 METHYLENEPROPANOATE; METHYL 3 (2 BENZYLOXY 3 ETHOXYPHENYL) 3 HYDROXY 2 (PIPERIDINOMETHYL)PROPANOATE; METHYL 3 (2 BENZYLOXY 3 ETHOXYPHENYL) 3 HYDROXY 2 METHYLENEPROPANOATE; METHYL 3 (2 BENZYLOXY 3 METHOXYPHENYL) 3 HYDROXY 2 (PIPERIDINOMETHYL)PROPANOATE; METHYL 3 (2 BENZYLOXY 3 METHOXYPHENYL) 3 HYDROXY 2 METHYLENEPROPANOATE; METHYL 3 (2 BENZYLOXY 3,5 DIBROMOPHENYL) 3 HYDROXY 2 METHYLENEPROPANOATE; METHYL 3 (2 BENZYLOXY 5 BROMOPHENYL) 3 HYDROXY 2 (PIPERIDINOMETHYL)PROPANOATE; METHYL 3 (2 BENZYLOXY 5 BROMOPHENYL) 3 HYDROXY 2 METHYLENEPROPANOATE; METHYL 3 (2 BENZYLOXY 5 CHLOROPHENYL) 3 HYDROXY 2 (PIPERIDINOMETHYL)PROPANOATE; METHYL 3 (2 BENZYLOXYPHENYL) 3 HYDROXY 2 (PIPERIDINOMETHYL)PROPANOATE; NOVOBIOCIN; PIPERIDINE; SALICYLALDEHYDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; CONJUGATION; CYCLIZATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; VIRUS REPLICATION;

EID: 0038583512     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120018937     Document Type: Article

References (25)

1. Murray, R.D.H. Progress in the Chemistry of Natural Products; Herz, W., Grisebach, H., Kirby, G.W., Eds.; Springer-Verlag: Wien-New York, 1978; 199-429.
2. Hermodson, M.A.; Barker, W.M.; Link, K.P. J. Med. Chem. 1971, 14, 167; Conlin, G.M.; Gear, J.R. J. Nat. Prod. 1993, 56 (8), 1402-1405.
3. Hermodson, M.A.; Barker, W.M.; Link, K.P. J. Med. Chem. 1971, 14, 167; Conlin, G.M.; Gear, J.R. J. Nat. Prod. 1993, 56 (8), 1402-1405.
4. Periers, A.-M.; Laurin, P.; Benedetti, Y.; Lachaud, S.; Ferroud, D.; Iltis, A.; Haesslein, J.-L.; Klich, M.; L'Hermite, G.; Musicki, B. Tetrahedron Lett. 2000, 41, 867-871; Peixoto, C.; Laurin, P.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Tetrahedron Lett. 2000, 41, 1741-1745.
5. Periers, A.-M.; Laurin, P.; Benedetti, Y.; Lachaud, S.; Ferroud, D.; Iltis, A.; Haesslein, J.-L.; Klich, M.; L'Hermite, G.; Musicki, B. Tetrahedron Lett. 2000, 41, 867-871; Peixoto, C.; Laurin, P.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Tetrahedron Lett. 2000, 41, 1741-1745.
6. Fuller, R.W.; Bokesch, H.R.; Gustafson, K.R.; McKee, T.C.; Cardellina, J.H. II; McMahon, J.B.; Cragg, G.M.; Soejarto, D.D.; Boyd, M.R. Bioinorganic and Medicinal Chemistry Letters 1994, 4 (16), 1961-1964.
7. Bode, M.L.; Kaye, P.T. J. Chem Soc., Perkin Trans. 1 1990, 2612-2613.
8. Familoni, O.B.; Kaye, P.T.; Klaas, P.J. Chem. Commun. 1998, 2563-2564.
9. Kaye, P.T.; Robinson, R.S. Synth. Commun. 1996, 26, 2085-2097.
10. Bacsa, J.; Kaye, P.T.; Robinson, R.S. S. Afr. J. Chem. 1998, 51 (1), 47-54; Bode, M.L.; English, R.B.; Kaye, P.T. S. Afr. J. Chem. 1992, 45 (1), 25-27.
11. Bacsa, J.; Kaye, P.T.; Robinson, R.S. S. Afr. J. Chem. 1998, 51 (1), 47-54; Bode, M.L.; English, R.B.; Kaye, P.T. S. Afr. J. Chem. 1992, 45 (1), 25-27.
12. Kaye, P.T.; Nocanda. X.W. J. Chem. Soc., Perkin Trans. 1 2000, 1331-1332.
13. Kaye, P.T.; Nocanda, X.W. Synthesis 2001, (16), 2389-2392.
14. Robinson, R. Ph.D. thesis, Rhodes University, 1997.
15. Drewes, S.E.; Njamela, O.L.; Emslie, N.D.; Ramesar, N.; Field, J.S. Synth. Commun. 1993, 23 (20), 2807-2815.
16. Weir, J.R.; Patel, B.A.; Heck, R.F. J. Org. Chem. 1980, 45, 4926-4931.
17. Harris, T.D.; Roth, G.P. J. Org. Chem. 1979, 44 (12), 2004-2007.
18. Merz, K.W.; Fink, J. Arch. Pharm. 1956, 289, 347-358; Chem. Abstr. 1957, 51, 3498a.
19. Merz, K.W.; Fink, J. Arch. Pharm. 1956, 289, 347-358; Chem. Abstr. 1957, 51, 3498a.
20. Profft, E. J. Prakt. Chem. [4], 1957, 5, 175-181. Chem. Abstr. 1958, 52, 10940d.
21. Profft, E. J. Prakt. Chem. [4], 1957, 5, 175-181. Chem. Abstr. 1958, 52, 10940d.
22. Raiford, L.; Chas.; Tanzer, L.K. J. Org. Chem. 1941, 6, 722-731.
23. Cartwright, G.A.; McNab, H. J. Chem. Res. (S) 1997, 296-297.
24. The chemical shift data reported in this format reflect a mixture (1:1.7) of the geometric isomers.
25. The COSY spectrum indicates weak coupling to the allylic methyl protons and to an aromatic proton.