Site-selective Suzuki-Miyaura reactions of the bis(triflate) of 1,3-dihydroxythioxanthone

Tetrahedron Letters

Volumn 52, Issue 27, 2011, Pages 3451-3454

  Zinad, Dhafer Saber ^a   Hussain, Munawar ^a   Akrawi, Omer Adeeb ^a   Villinger, Alexander ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Catalysis; Palladium; Regioselectivity; Suzuki Miyaura reaction; Thioxanthones

Indexed keywords

1,3 DIHYDROXYTHIOXANTHONE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; SUZUKI REACTION;

EID: 79957946930     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.102     Document Type: Article

References (39)

1. M.P. Wentland, R.B. Perni, A.G. Hlavac, T.H. Corbett, S.A. Coughlin, and J.B. Rake Bioorg. Med. Chem. Lett. 4 1994 609
2. M. Watanabe, M. Pate, M. Tsukazaki, and S. Furukawa Chem. Pharm. Bull. 37 1989 36
3. H.D.H. Showalter, M.M. Angelo, and E.M. Berman J. Med. Chem. 31 1988 1527
4. L. Vacek, and H.M. Foster Chem. Abstr. 90 1979 72060a
5. S. Archer, L.P. Mattoccia, D. Cioli, A. Seyed-Mozaffari, and A.H. Zayed J. Med. Chem. 31 1988 254
6. G.M. Laidlaw, J.C. Collins, S. Archer, D. Rosi, and J.W. Schulenberg J. Org. Chem. 38 1973 1743
7. B.J. Foster, R.A. Wiegand, S.P. Partricia, M. LoRusso, J. Rake, and T.H. Corbett Clin. Cancer Res. 3 1997 2047
8. J.P. Horwitz, I. Massova, T.E. Wiese, B.H. Besler, and T.H. Corbett J. Med. Chem. 37 1994 781
9. A. Banerji, A.D. Deshpande, B.R. Prabhu, and P. Pradhan J. Nat. Prod. 57 1994 396
10. D. Rosi, G. Peruzzoti, E.W. Dennis, D.A. Berberian, H. Freele, B. Tullar, and S. Archer J. Med. Chem. 10 1967 867
11. R.B. Perni, M.P. Wentland, J.I. Huang, R.G. Powles, S. Aldous, K.M. Klingbeil, A.D. Peverly, R.G. Robinson, T.H. Corbett, J.L. Jones, K.C. Mattes, J.B. Rake, and S.A. Coughlin J. Med. Chem. 41 1998 3645
12. I. Kostakis, N. Pouli, P. Marakos, E. Mikros, A. Skaltsounis, S. Leonce, G. Atassi, and P. Renard Bioorg. Med. Chem. 9 2001 2793
13. G.M. Kolokythas, I. Kostakis, N. Pouli, P. Marakos, D. Kletsasb, and B. Pratsinis Bioorg. Med. Chem. 11 2003 4591
14. M. Harfenist, D.J. Heuser, C.T. Joyner, J.F. Batchelor, and H.L. White J. Med. Chem. 39 1996 1857
15. J. Zhao, and R.C. Larock J. Org. Chem. 72 2007 583
16. H. Morita, S. Mori, and T. Yamaoka Bull. Chem. Soc. Jpn. 61 1988 191
17. R. Ran, and U.C. Pittman J. Heterocycl. Chem. 30 1993 1673
18. I. Okabayashi, and H. Fujiwara J. Heterocycl. Chem. 31 1994 733
19. I. Okabayashi, H. Fujiwara, and C. Tanaka J. Heterocycl. Chem. 28 1991 1977
20. S. Schröter, C. Stock, and T. Bach Tetrahedron 61 2005 2245
21. M. Schnürch, R. Flasik, A.F. Khan, M. Spina, M.D. Mihovilovic, and P. Stanetty Eur. J. Org. Chem. 2006 3283
22. For Suzuki-Miyaura reactions of bis(triflates) of benzene derivatives and other arenes, see for example: M. Takeuchi, T. Tuihiji, and J. Nishimura J. Org. Chem. 58 1993 7388
23. H. Sugiura, Y. Nigorikawa, Y. Saiki, K. Nakamura, and M. Yamaguchi J. Am. Chem. Soc. 126 2004 14858
24. K. Akimoto, H. Suzuki, Y. Kondo, K. Endo, U. Akiba, Y. Aoyama, and F. Hamada Tetrahedron 63 2007 6887
25. K. Akimoto, Y. Kondo, K. Endo, M. Yamada, Y. Aoyama, and F. Hamada Tetrahedron Lett. 49 2008 7361
26. S. Hosokawa, H. Fumiyama, H. Fukuda, T. Fukuda, M. Seki, and K. Tatsuta Tetrahedron Lett. 48 2007 7305
27. M. Nawaz, M. Farooq Ibad, A. Obaid-Ur-Rahman, R.A. Khera, A. Villinger, and P. Langer Synlett 2010 150
28. A. Mahal, A. Villinger, and P. Langer Synlett 2010 1085
29. M. Nawaz, M.F. Ibad, O.-U.-R. Abid, R.A. Khera, A. Villinger, and P. Langer Synlett 2010 150
30. O.-U.-R. Abid, M.F. Ibad, M. Nawaz, A. Ali, M. Sher, N.H. Rama, A. Villinger, and P. Langer Tetrahedron Lett. 51 2010 1541
31. O.A. Akrawi, M. Hussain, and P. Langer Tetrahedron Lett. 52 2011 1093
32. H. Sharghi, and S. Beni Synthesis 2004 2900
33. +): 507.91744; found: 507.916890.
34. 4), filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (flash silica gel, heptanes-EtOAc).
35. +: 499.05858; found: 499.058160.
36. 2: 466.01510; found: 466.015129.
37. CCDC-821684 (5b) and CCDC-821685 (6b) contain all crystallographic details of this publication and are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: (+44)1223 336 033; or deposit@ccdc.cam.ac.uk.
38. +: 458.07379; found: 458.074006.
39. 1H NMR chemical shift values, see: S.T. Handy, and Y. Zhang Chem. Commun. 2006 299