Synthesis of 9-substituted xanthenes by the condensation of arynes with ortho-hydroxychalcones

Tetrahedron Letters

Volumn 53, Issue 17, 2012, Pages 2202-2205

  Lu, Chun ^a   Dubrovskiy, Anton V ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Arynes; Cesium carbonate; Michael addition; Nucleophilic; ortho Hydroxychalcones

Indexed keywords

2 HYDROXYCHALCONE DERIVATIVE; BASE; CHALCONE DERIVATIVE; OXIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MICHAEL ADDITION; POLYMERIZATION; REACTION ANALYSIS; REPRODUCIBILITY; SYNTHESIS;

EID: 84858698324     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.072     Document Type: Article

References (47)

1. C. Lu, and R.C. Larock Abstracts of Papers, 235th National Meeting of the American Chemical Society 2008 New Orleans LA, Aug 6-10
2. X. Huang, and T. Zhang J. Org. Chem. 75 2010 506
3. N. Sekar Colourage 50 2003 59
4. F. Catalina, R. Santamaria, P. Bosch, and C. Peinado Revista de Plasticos Modernos 529 2000 38
5. N. Sekar Colourage 46 1999 43
6. D.C. Neckars, and O.M. Valdes-Aguilera Adv. Photochem. 18 1993 315
7. Farris, R. E. Kirk-Othmer Encycl. Chem. Technol., 3rd Ed. 1983, 24, 662.
8. M. Carmen de la Fuente, and D. Domínguez J. Org. Chem. 72 2007 8804
9. R. Pellicciari, G. Costantino, M. Marinozzi, A. Macchiarulo, L. Amori, P.J. Flor, F. Gasparini, R. Kuhn, and S. Urwyler Bioorg. Med. Chem. Lett. 11 2001 3179
10. B. Henkel, W. Zeng, and E. Bayer Tetrahedron Lett. 38 1997 3511
11. K. McWilliams, and J.W. Kelly J. Org. Chem. 61 1996 7408
12. G.J. Bennett, and H.H. Lee Phytochemistry 28 1989 967
13. C.P. Wu, A. Donelly, V. Schalkwyk, D. Taylor, P.J. Smith, and K. Chibale Int. J. Antimicrob. Ag. 26 2005 170
14. K. Chibale, M. Visser, D.V. Schalkwyk, P.J. Smith, A. Saravanamuthu, and A.H. Fairlamb Tetrahedron 59 2003 2289
15. Burmester, J. K. U. S. Patent WO 2006102102, 2006.
16. Xiao, Y.; Ottenbrite, R. U. S. Patent WO 2006083869, 2006.
17. Greene, M. I.; Murali, R.; Cheng, X.; Ottenbrite, R.; Xiao, Y. U. S. Patent WO 2006083970, 2006.
18. A.I. Zhebentyaev, A.K. Zhernosek, S.I. Egorava, and N.O. Mchedlov-Petrosyan J. Anal. Chem. 52 1997 856
19. T. Nagano, Y. Urano, and S. Kenmoku J. Am. Chem. Soc. 129 2007 10324
20. N. Fitchen, P. O'Shea, P. Williams, and K.R. Hardie Mol. Immunol. 40 2003 407
21. J.D. Hepworth, C.D. Gabutt, and B.M. Heron A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II vol. 5 1996 Elsevier Science Ltd. Oxford 379 For recent contributions, see
22. C. Scala-Valero, D. Doizi, and G. Guillaumet Tetrahedron Lett. 40 1999 4803
23. O. Sirkecioglu, N. Talinli, and A. Akar J. Heterocycl. Chem. 35 1998 457
24. M. Ruth, and W. Steglich Synthesis 2000 677
25. M.B. Dinger, and M.J. Scott J. Chem. Soc., Perkin Trans. 1 2000 1741
26. L. Novak, P. Kovacs, G. Pirok, P. Kolonits, E. Szabo, J. Fekete, V. Weiszfeiler, and C. Szantay Synthesis 1995 693
27. R.J. Caruso, and J.L. Lee J. Org. Chem. 62 1997 1058
28. R.M. Letcher, T.Y. Yue, K.F. Chiu, A.S. Kelkar, and K.K. Cheung J. Chem. Soc., Perkin Trans. 1 1998 3267
29. R. Vázquez, M.C. de la Fuente, L. Castedo, and D. Domínguez Synlett 1994 433
30. A. Mustafa, W. Asker, and M.E.E. Sobhy J. Am. Chem. Soc. 77 1955 5121
31. H. Gilman, and J. Diehl J. Org. Chem. 26 1961 4817
32. J. Shi, X. Zhang, and D.C. Neckers J. Org. Chem. 57 1992 4418
33. N.D. Xuong, and N.P. Buu-Hoi J. Chem. Soc. 1952 3741
34. Y. Himeshina, T. Sonoda, and H. Kobayashi Chem. Lett. 1983 1211
35. Z. Liu, and R.C. Larock J. Org. Chem. 71 2006 3198
36. Z. Liu, and R.C. Larock Org. Lett. 1 2004 99
37. Z. Liu, and R.C. Larock Org. Lett. 24 2003 4673
38. H. Yoshida, E. Shiakawa, Y. Honda, and T. Hiyama Angew. Chem., Int. Ed. 41 2002 3247
39. U.K. Tambar, and B.M. Stoltz J. Am. Chem. Soc. 127 2005 5340
40. Z. Liu, and R.C. Larock J. Am. Chem. Soc. 127 2005 13112
41. D.G. Pintori, and M.F. Greaney Org. Lett. 12 2010 168
42. H. Yoshida, Y. Mimura, J. Ohshita, and A. Kunai Chem. Commun. 23 2007 2405
43. J. Zhao, and R.C. Larock Org. Lett. 19 2005 4273
44. J. Zhao, and R.C. Larock J. Org. Chem. 72 2007 583
45. 1 M Tetrabutylammonium fluoride in THF solution with 5% water.
46. R. Sanz Org. Prep. Proced. Int. 40 2008 215
47. P.H.-Y. Cheong, R.S. Paton, S.M. Bronner, G.-Y.J. Im, N.K. Garg, and K.N. Houk J. Am. Chem. Soc. 132 2010 1267