Friedel-Crafts cyclization of tertiary alcohols using bismuth(III) triflate

Tetrahedron Letters

Volumn 54, Issue 32, 2013, Pages 4330-4332

  Nammalwar, Baskar ^a   Bunce, Richard A ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

Bismuth(III) triflate; Friedel Crafts cyclization; Heterocycles; Tertiary alcohols

Indexed keywords

ALCOHOL; BISMUTH; CHROMAN DERIVATIVE; LEWIS ACID; QUINOLINE DERIVATIVE; TETRAHYDROISO QUINOLINE DERIVTIVE; TETRAHYDRONAPTHALENE; TETRAHYDROQUINOLINE DERIVATIVE; THIOCHROMAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; FRIEDEL CRAFTS REACTION;

EID: 84879836928     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.06.026     Document Type: Article

References (43)

1. J. Vasudevan, A.T. Johnson, D. Huang, L. Wang, and R.A. Chandraratna Chem. Abstr. 136 2002 216646 World Patent WO 2002018361 (2002)
2. M. Pfahl, C. Tachdjian, H.A. Al-Shamma, A. Fanjul, D.P.M. Pleynet, L.W. Spruce, R. Fine, and J.W. Zapf Chem. Abstr. 127 2002 226654 World Patent WO 2002072543 (2002)
3. G. Benoit, M. Gronemeyer, D. Lanotte, and M. Gottardis Chem. Abstr. 139 2013 255334 US Patent 6624154 (2003)
4. J. Germain, B.C. Askew Jr., D. Bauer, D. Choquette, L.V. Dipietro, R. Graceffa, J.-C. Harmanage, Q. Huang, J.L. Kim, D. La, A. Li, N. Nishimura, R. Nomack, V. Patel, M. Potashman, B. Riahi, T. Storz, S. van der Plas, K. Yang, and C.C. Yuan Chem. Abstr. 146 2007 462141 WO2007048070 (2007)
5. C. Parmenon, J. Guillard, D.-H. Caignard, N. Hennuyer, B. Staels, V. Audinot-Bouchez, J.-A. Boutin, C. Dacquet, A. Ktorza, and M.-C. Vivaud-Massuard Bioorg. Med. Chem. Lett. 18 2008 1617 1622
6. C. Parmenon, J. Guillard, D.-H. Caignard, N. Hennuyer, B. Staels, V. Audinot-Bouchez, J.-A. Boutin, C. Dacquet, A. Ktorza, and M.-C. Vivaud-Massuard Bioorg. Med. Chem. Lett. 19 2009 2683 2687
7. B. Nammalwar, R.A. Bunce, D.M. Benbrook, T. Lu, H.-F. Li, Y.-D. Chen, and K.D. Berlin Phosphorus Sulfur Silicon Relat. Elem. 186 2011 189 204
8. M. Alvarez, M. Salas, and J.A. Joule Heterocycles 32 1991 759 794
9. G.W. Gribble A.R. Katritzky, Comprehensive Heterocyclic Chemistry II Vol. 2 1996 Pergamon UK 207 257
10. M. Balasubramanian, and J.G. Keay A.R. Katritzky, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Pergamon UK 247 300
11. B.A. Keay, and P.W. Dibble A.R. Katritzky, Comprehensive Heterocyclic Chemistry II Vol. 2 1996 Pergamon UK 395 436
12. G.R. Geen, J.M. Evans, and A.K. Vong A.R. Katritzky, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Pergamon UK 470 500
13. Y.-C. Xu Recent Res. Dev. Org. Chem. 4 2000 423 441
14. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945 2964
15. M. Shibasaki, E.M. Vogl, and T. Ohshima Adv. Synth. Catal. 346 2004 1533 1552
16. T. Kametani, and K. Fukumoto Chemistry of Heterocyclic Compounds 1981 Wiley & Sons Chichester, UK 139 274
17. V.M. Kisel, E.O. Kostyrko, and V.A. Kovtunenko Chemistry of Heterocyclic Compounds Vol. 38 2002 Plenum Publishing New York 1295 1318
18. H.M.R. Hoffmann, B. Schmidt, and S. Wolff Tetrahedron 45 1989 6113 6126
19. N. Kurono, E. Honda, F. Komatsu, K. Orito, and M. Tokuda Tetrahedron 60 2004 1791 1801
20. M. Arisawa, Y. Terasa, C. Theeraladanon, K. Takahashi, M. Nagagawa, and A. Nishida J. Organomet. Chem. 690 2005 5398 5406
21. I. Nakamura, and Y. Yamamoto Chem. Rev. 104 2004 2127 2198
22. L.F. Tietze, H. Lla, and H.P. Bell Chem. Rev. 104 2004 3453 3516
23. R.E. Ziegert, J. Torang, K. Knepper, and S. Brase J. Comb. Chem. 7 2005 147 169
24. K. Yip, M. Yang, K. Law, N. Zhu, and D. Yang J. Am. Chem. Soc. 128 2006 3130 3131
25. P. Liu, L. Huang, Y. Lu, M. Dilmeghani, J. Baum, T. Xiang, J. Adams, A. Tasker, R. Larsen, and M.M. Faul Tetrahedron Lett. 48 2007 2307 2310
26. 3: C.R. Tallent, C.E. Twine Jr., P. Risbood, and H.H. Seltzman Org. Prep. Proced. Int. 39 2007 96 101
27. R.A. Bunce, N.R. Cain, and J.G. Cooper Org. Prep. Proced. Int. 45 2013 28 43
28. 2O: I. Iovel, K. Mertins, J. Kischel, A. Zapf, and M. Beller Angew. Chem., Int. Ed. 44 2005 3913 3917
29. C. Liebert, M.K. Brinks, A.G. Capacci, M.J. Fleming, and M. Lautens Org. Lett. 13 2011 3000 3003
30. R.A. Bunce, N.R. Cain, and J.G. Cooper Org. Prep. Proced. Int. 44 2012 131 145
31. Amberlyst-15: R.A. Bunce, and A.N. Cox Org. Prep. Proced. Int. 42 2010 83 93
32. 4: M.T. Bogert, D. Davidson, and P.M. Apfelbaum J. Am. Chem. Soc. 56 1934 959 963
33. PPA: R.B. Miller, and C.G. Gutierrez J. Org. Chem. 43 1978 1569 1573
34. C.W. Brown, S. Liu, J. Klucik, K.D. Berlin, P.J. Brennan, D. Kaur, and D.M. Benbrook J. Med. Chem. 47 2004 1008 1017
35. D.M. Benbrook, S.A. Kamelle, S.B. Guruswamy, S.A. Lightfoot, T.L. Rutledge, N.S. Gould, B.N. Hannafon, S.T. Dunn, and K.D. Berlin Invest. New Drugs 23 2005 417 428
36. Y. Lin, X. Liu, P. Yue, D.M. Benbrook, K.D. Berlin, F.R. Khuri, and S.-Y. Sun Mol. Cancer Ther. 7 2008 3556 3565
37. Y.-D. Lin, S. Chen, P. Yue, W. Zou, D.M. Benbrook, S. Liu, T.C. Le, K.D. Berlin, F.R. Khuri, and S.-Y. Sun Cancer Res. 68 2008 5335 5344
38. T. Liu, C. Masamha, S. Chengedza, K.D. Berlin, S. Lightfoot, F. He, and D.M. Benbrook Mol. Cancer Ther. 8 2009 1227 1238
39. N.M. Leonard, L.C. Wieland, and R.S. Mohan Tetrahedron 58 2002 8373 8397
40. 3 for the Friedel-Crafts cyclization of a tertiary alcohol, see M. Rueping, B.J. Nachtsheim, and W. Ieawsuwan Adv. Synth. Catal. 348 2006 1033 1037
41. J. Cologne, E. LeSech, and R. Marey Bull. Soc. Chim. Fr. 1957 776 779
42. L.W. Spruce, J.B. Gale, K.D. Berlin, A.K. Verma, T.R. Breitman, X. Ji, and D. van der Helm J. Med. Chem. 34 1991 430 439
43. B. Cacciuttolo, S. Poulain-Martini, and E. Duñach Eur. J. Org. Chem. 2011 3710 3714