Reaction of salicyl N-tosylimines with 2-cyclohexenone: A facile access to tetrahydroxanthenones

Synlett

Volumn , Issue 17, 2005, Pages 2623-2626

  Shi, Yong Ling ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

2 cyclohexenone; 2 cyclopentenone; Aza baylis hillman reaction; Salicyl N tosylimine; Tetrahydroxanthenone

Indexed keywords

2 CYCLOHEXENONE; 2 CYCLOPENTEN 1 ONE; ALKANONE; IMINE; SALICYL N TOSYLIMINE; TETRAHYDROXANTHENONE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL STRUCTURE; REACTION TIME;

EID: 27444444356     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917109     Document Type: Article

References (24)

1. (a) Dua, V. K.; Ojha, V. P.; Roy, R.; Joshi, B. C.; Valecha, N.; Devi, C. U.; Bhatnagar, M. C.; Sharma, V. P.; Subbarao, S. K. J. Ethnopharmacol. 2004, 95, 247.
2. (b) Statzger, H.; Schmidt, B.; Root, C.; Zinth, W.; Fierz, B.; Krieger, F.; Kiefhaber, T.; Gilch, P. J. Phys. Chem. A 2004, 108, 10072.
3. (c) Goez, M.; Hussein, B. H. M. PhysChemChemPhys. 2004, 6, 5490.
4. (d) Itoigawa, M.; Ito, C.; Tokuda, H.; Enjo, F.; Nishino, H.; Furukawa, H. Cancer Lett. 2004, 214, 165.
5. (e) Milnesi, S.; Fagnoni, M.; Albini, A. J. Org. Chem. 2005, 70, 603.
6. (a) Sultanbawa, M. U. S. Tetrahedron 1980, 36, 1465.
7. (b) Holker, J. S.; O'Brien, T. E.; Simpson, T. J. J. Chem. Soc., Perkin Trans. 1 1983, 1365.
8. (c) Hase, K.; Kadota, S.; Basnet, P.; Li, J.; Takamura, S.; Namba, T. Chem. Pharm. Bull. 1997, 45, 567.
9. Lesch, B.; Bräse, S. Angew. Chem. Int. Ed. 2004, 43, 115.
10. (a) Shi, M.; Xu, Y.-M. Chem. Commun. 2001, 1876.
11. (b) Shi, M.; Xu, Y.-M. Eur. J. Org. Chem. 2002, 696.
12. (c) Shi, M.; Xu, Y.-M.; Zhao, G.-L.; Wu, X.-F. Eur. J. Org. Chem. 2002, 3666.
13. (d) Shi, M.; Xu, Y.-M. J. Org. Chem. 2004, 69, 417.
14. (e) Shi, Y.-L.; Xu, Y.-M.; Shi, M. Adv. Synth. Catal. 2004, 346, 1220.
15. 2 = 0.1352.
16. For a review related concurrent tandem catalysis, see: Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
17. (a) Kaye, P. T.; Musa, M. A.; Nocanda, X. W.; Robinson, R. S. Org. Biomol. Chem. 2003, 1, 1133.
18. (b) Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin, M. N. Angew. Chem. Int. Ed. 2004, 43, 4330.
19. (c) Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org. Lett. 2005, 7, 147.
20. (d) Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones, G. C. Angew. Chem. Int. Ed. 2005, 44, 1706.
21. (e) Lesch, B.; Toräng, J.; Vanderheiden, S.; Bräse, S. Adv. Synth. Catal. 2005, 347, 555.
22. (f) Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980.
23. (g) Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 3057.
24. 2, EtOAc-PE = 1:10) to yield 4a (86 mg, 86%) as a yellow solid.