New and facile synthesis of 3-styrylflavones

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6761-6764

  Lokshin, Vladimir ^a   Heynderickx, Arnault ^a   Samat, André ^a   Pèpe, Gérard ^a   Guglielmetti, Robert ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Carbonyl compounds; Condensation; Cyclisation; Flavones

Indexed keywords

ALDEHYDE; BENZENE DERIVATIVE; FLAVONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0033543522     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01301-5     Document Type: Article

References (19)

1. (a) Chromenes, Chromanones, and Chromones; Ellis, G. P., Ed.; John Wiley: New York, 1977.
2. (b) The Flavonoids; Harborne, J. B.; Mabry, T. L.; Mabry, H., Eds.; Chapman and Hall: London, 1975.
3. (c) The Flavonoids - Advances in Research since 1980; Harborne, J. B., Ed.; Chapman and Hall: London, 1988.
4. (d) The Flavonoids - Advances in Research since 1986; Harborne, J. B., Ed.; Chapman and Hall: London, 1994.
5. (e) Dauzonne, D.; Folleas, B.; Martinez, L.; Chabot, G. G. Eur. J. Med. Chem. 1997, 32, 71-82.
6. Price, W. A.; Silva, A. M. S.; Cavaleiro, J. A. S. Heterocycles 1993, 36(11), 2601-2612, and references cited therein.
7. (a) Ghosh, C. K.; Ghosh, C. Indian J. Chem. 1997, 36B, 968-980.
8. (b) Silva, A. M. S.; Pinto, D. C. G. A.; Tavares, H. R.; Cavaleiro, J. A. S.; Jimeno, M. L.; Elguero, J. Eur. J. Org. Chem. 1998, 2031-2038.
9. (c) Silva, A. M. S.; Silva, A. M. G.; Tome, A. C.; Cavaleiro, J. A. S. J. Eur. J. Org. Chem. 1999, 135-139.
10. Reddy, B. P.; Krupadanam, G. L. D. J. Heterocyclic Chem. 1996, 33, 1561-1565, and references cited therein.
11. Silva, A. M. S.; Cavaleiro, J. A. S.; Elguero, J. Liebigs. Ann. 1997, 2065-2068, and references cited therein.
12. Goyal, S.; Parthasarathy, M. R. Indian J. Chem. 1992, 31B, 391-395.
13. Compounds 5, 9 and 10 were purified by silica gel column chromatography.
14. 3, δ ppm): 117.9 (s); 118.1 (d); 120.4 (d); 123.8 (s); 125.4 (d); 126.5 (d); 126.8 (d); 127.8 (d); 128.8 (d); 130.1 (d); 131.0 (d); 133.5 (s); 133.7 (d); 134.7 (d); 138.5 (s); 155.7 (s); 163.3 (s); 177.7 (s).
15. Satisfactory microanalyses were obtained for all new compounds.
16. 2). Atomic co-ordinates, thermal parameters and bond lengths and angles have been deposited at the Cambridge Crystallographic Data Centre.
17. The 1,3-diketones 1a, 1b, 1d and the aldehyde 2a were commercially available from Aldrich®.
18. (a) Huffmann, K. R.; Kuhn, C. E.; Zweig, A. J. Am. Chem. Soc. 1970, 92, 599-605.
19. (b) Cummings, R. T.; Dizio, J. P.; Krafft, G. A. Tetrahedron Lett. 1988, 29, 69-72.