Functionalization of anthracene by strategic utilization of the Diels-Alder reaction and the ring-closing metathesis

Journal of the Indian Chemical Society

Volumn 90, Issue 10, 2013, Pages 1789-1794

  Kotha, Sambasivarao ^a   Meshram, Milind ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Anthracene; C C bond cleavage; Diels Alder reaction; Grignard reaction; Ring closing metathesis

Indexed keywords

ANTHRACENE DERIVATIVE; ANTHRAQUINONE; DIKETONE;

ALLYLATION; AROMATIZATION; ARTICLE; ATMOSPHERIC PRESSURE; CARBON NUCLEAR MAGNETIC RESONANCE; DEHYDROGENATION; DIELS ALDER REACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 84891333201     PISSN: 00194522     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. (a) J. C. C. Atherton and S. Jones, Tetrahedron, 2003, 59, 9039;
2. (b) P. Hodge, G. A. Power and M. A. Rabjohns, Chem. Commun., 1997, 73;
3. (c) H. Yamada, Y. Yamashita, M. Kikuchi, H. Watanabe, T. Okujima, T. Ogawa, K. Ohara and N. Ono, Chem. Eur. J., 2005, 11, 6212;
4. (c) I. Okamoto, T. Ohwada and K. Shudo, J. Org. Chem., 1996, 61, 3155.
5. S. Kotha, Acc. Chem. Res., 2003, 36, 342.
6. (a) S. Kotha, A. K. Ghosh and M. Behera, Indian J. Chem., Sect. B, 2002, 41, 2330;
7. (b) B. V. Yang and L. M. Doweyko, Tetrahedron Lett., 2005, 46, 2857;
8. (c) J.-F. Lohier, K. Wight, C. Peggion, F. Formaggio, C. Toniolo, M. Wakselman and J. -P. Mazaleyrat, Tetrahedron, 2006, 62, 6203.
9. (a) A. Suzuki, N. Miyaura and K. Yamada, Tetrahedron Lett., 1979, 36, 3437;
10. (b) A. Suzuki and N. Miyaura, J. Chem. Soc., Chem. Commun., 1979, 866;
11. (c) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457;
12. (d) S. Kotha, K. Lahiri and D. Kashinath, Tetrahedron, 2002, 58, 9633;
13. (e) S. Kotha and K. Lahiri, Eur. J. Org. Chem., 2007, 1221.
14. (a) S. Kotha and A. K. Ghosh, Synlett, 2002, 451;
15. (b) S. Kotha, V. R. Shah, P. P. Mishra and A. Datta, Amino Acid, 2008, 35, 83;
16. (c) S. Kotha, A. K. Ghosh and K. D. Deodhar, Synthesis, 2004, 549;
17. (d) S. Kotha and V. R. Shah, Synthesis, 2008, 3653.
18. (a) O. Diels and K. Alder, Liebigs Ann. Chem., 1931, 486, 191;
19. (b) W. Carruthers, "Cycloaddition Reactions in Organic Synthesis", 'Tetrahedron Organic Chemistry Series', Vol. 8, Pergamon Press, 1990;
20. (c) F. Fringuelli and A. Taticchi, "The Diels-Alder Reaction, Selected Practical Methods", John Wiley & Sons, Ltd., England, 2002.
21. (a) R. H. Grubbs, Tetrahedron, 2004, 60, 7117;
22. (b) S. Kotha and K. Lahiri, Synlett, 2007, 2767;
23. (c) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012;
24. Angew. Chem., 2000, 112, 3140.
25. (a) R. Mondal, B. K. Shah and D. C. Neckers, J. Am. Chem. Soc., 2006, 128, 9612;
26. (b) H. Yamada, Y. Yamashita, M. Kikuchi, H. Watanabe, T. Okujima, T. Ogawa, K. Ohara and N. Ono, Chem. Eur. J., 2005, 11, 6212;
27. (c) M. W. Wright and M. E. Welker, J. Org. Chem., 1996, 61, 133;
28. (d) T. Kobayashi and S. Kobayashi, Molecules, 2000, 5, 1062.
29. (a) G. H. Posner and T. D. Nelson, Tetrahedron, 1990, 46, 4573;
30. (b) S. Vijgen, K. Nauwelaerts, J. Wang, A. V. Aerschot, I. Lagoja and P. Herdewijn, J. Org. Chem., 2005, 70, 4591;
31. (c) M. S. Newman and R. W. Addor, J. Org. Chem., 1955, 77, 3790.
32. (a) J. Mendez-Andino and L. A. Paquette, Org. Lett., 2000, 2, 1263;
33. (b) E. P. Balskus, J. Mendez-Andino, R. M. Arbit and L. A. Paquette, J. Org. Chem., 2001, 66, 6695.