New synthesis of 2,3-diarylxanthones

Synlett

Volumn , Issue 20, 2005, Pages 3095-3098

  Santos, Clementina M M ^a,b   Silva, Artur M S ^b   Cavaleiro, José A S ^b  

^a INSTITUTO POLITÉCNICO DE BRAGANÇA   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

2 styrylchromones; 3 bromo 2 methylchromone; Diarylxanthones; Electrocyclisation; Heck reaction

Indexed keywords

3 BROMO 2 METHYLCHROMONE; 3 BROMO 2 STYRYLCHROMONE; BENZALDEHYDE; BROMINE; CHROMONE DERIVATIVE; HETEROCYCLIC COMPOUND; PALLADIUM; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 29744458203     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921928     Document Type: Article

References (36)

1. (a) Hostettman, K.; Hostettman, M. In Methods in Plant Biochemistry: Plant Phenolics; Dey, P. M.; Harbone, J. B., Eds.; Academic Press: New York, 1989, Vol. 1, 493.
2. (b) Bennett, G. J.; Lee, H.-H. Photochemistry 1989, 28, 967.
3. (a) Abdel-Lateff, A.; Klemke, C.; König, G. M.; Wright, A. D. J. Nat. Prod. 2003, 66, 706.
4. (b) Chiang, Y.-M.; Kuo, Y.-H.; Oota, S.; Fukuyama, Y. J. Nat. Prod. 2003, 66, 1070.
5. (c) Pedro, M.; Cerqueira, F.; Sousa, M. E.; Nascimento, M. S. J.; Pinto, N. Bioorg. Med. Chem. 2002, 10, 3725.
6. (d) Schaper, K.-J.; Pickert, M.; Frahm, A. W. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 91.
7. (e) Minami, H.; Kinoshita, M.; Fukuyama, Y.; Komoda, M.; Yoshizawa, T.; Sugiura, M.; Nakagawa, K.; Tago, H. Phytochemistry 1994, 36, 501.
8. Fukawa, I.; Yoneda, H.; Asahi, K. K. K. K. Eur. Pat. EP0237004, 1987.
9. Kelkar, A. S.; Letcher, R. M.; Cheung, K.-K.; Chiu, K.-F.; Brown, G. D. J. Chem. Soc., Perkin Trans. 1 2000, 3732.
10. (a) Cassilas, L. K.; Townsend, C. A. J. Org. Chem. 1999, 64, 4050.
11. (b) Afzal, M.; Al-Hassan, J. M. Heterocycles 1980, 14, 1173.
12. (c) Grover, P. K.; Shah, G. D.; Shah, R. C. J. Chem. Soc. 1955, 3982.
13. Mahal, H. S.; Venkataraman, K. J. Chem. Soc. 1934, 1767.
14. Ares, J. J.; Outt, P. E.; Kakodkar, S. V.; Buss, R. C.; Geiger, J. C. J. Org. Chem. 1993, 58, 7903.
15. Ibrahim, S. S. Ind. Eng. Chem. Res. 2001, 40, 37.
16. (a) Price, W. A.; Silva, A. M. S.; Cavaleiro, J. A. S. Heterocycles 1993, 36, 2601.
17. (b) Alonso, R.; Brossi, A. Tetrahedron Lett. 1988, 29, 735.
18. (c) Ayyangar, N. R.; Khan, R. A.; Desphande, V. H. Tetrahedron Lett. 1988, 29, 2347.
19. 2 as eluent. The solvent was evaporated to dryness and the residue was recrystallised from EtOH to give the 3-bromo-2-styryl-chromones 6a,b in good yields (Table 1).
20. 3: C, 66.53; H, 3.95. Found: C, 66.48; H, 4.27.
21. Bigi, F.; Conforti, M. L.; Maggi, R.; Piccinno, A.; Sartori, G. Green Chem. 2000, 2, 101.
22. (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442.
23. (b) Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
24. (c) Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559.
25. (d) Heidenreich, R. G.; Köhler, K.; Krauter, J. G. E.; Pietsch, J. Synlett 2002, 1118.
26. (e) Biffis, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001, 173, 249.
27. (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
28. 2-light PE as eluent). The product was crystallised from EtOH giving, in each case, the 2,3-diarylxanthones 9a-f (yields described in Table 2).
29. 2: 348.1150; found: 348.1158.
30. 2: 350.1307; found: 350.1315.
31. (a) Clarke, D. S.; Gabbutt, C. D.; Hepworth, J. D.; Heron, B. M. Tetrahedron Lett. 2005, 46, 5515.
32. (b) de Meijere, A.; Schelper, M.; Knoke, M.; Yucel, B.; Sünnemann, H. W.; Scheurich, R. P.; Arve, L. J. Organomet. Chem. 2003, 687, 249.
33. Santos, C. M. M.; Silva, A. M. S.; Cavaleiro, J. A. S. unpublished results.
34. 3: C, 82.52; H, 4.79. Found: C, 82.23; H, 4.94.
35. 3: 456.1725; found: 456.1735.
36. The relative stereochemistry of protons H-3 and H-4 is referred as cis and trans.