Generation of 1-(trifluoromethyl)-1,2-dihydroisoquinolines via a silver(I)-catalyzed reaction of 2-alkynylaryl aldimine with trimethyl(trifluoromethyl)silane

Tetrahedron Letters

Volumn 55, Issue 4, 2014, Pages 962-964

  Wang, Xianbo ^a   Qiu, Guanyinsheng ^b   Zhang, Ling ^a   Wu, Jie ^b,c  

^a NANCHANG UNIVERSITY   (China)

^b FUDAN UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1 (Trifluoromethyl) 1,2 dihydroisoquinoline; 2 Alkynylaryl aldimine; Amine; Silver hexafluorostiboranuide; Trimethyl(trifluoromethyl)silane

Indexed keywords

1 (TRIFLUOROMETHYL) 1,2DIHYDROISOQUINOLINE DERIVATIVE; 2 ALKYNYLARYL ALDIMINE; ANILINE; ISOQUINOLINE DERIVATIVE; SILVER; TRIMETHYL(TRIFLUOROMETHYL)SILANE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ELECTRON; SYNTHESIS;

EID: 84892440930     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.12.064     Document Type: Article

References (55)

1. R. Filler, and Y. Kobayashi Biomedicinal Aspects of Fluorine Chemistry 1982 Elsevier Amsterdam
2. J.T. Welch, and S. Eswarakrishman Fluorine in Bioorganic Chemistry 1991 Wiley New York
3. J.-P. Begue, and D. Bonnet-Delpon Bioorganic and Medicinal Chemistry of Fluorine 2008 Wiley Hoboken
4. For some reviews on the synthesis of fluorinated heterocycles, see: V.A. Petrov Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications 2009 John Wiley & Sons Inc. Hoboken, NJ
5. E.V. Nosova, G.N. Lipunova, V.N. Charushin, and Q.N. Chupakhin J. Fluorine Chem. 131 2010 1267
6. S. Zhu, Y. Wang, W. Peng, L. Song, and G. Jin Curr. Org. Chem. 6 2002 1057
7. M.J. Silvester Aldrichim. Acta 24 1991 31
8. For some selective examples, see: P. Kwiatkowski, T.D. Beeson, J.C. Conrad, and D.W.C. MacMillan J. Am. Chem. Soc. 133 2011 1738
9. Y. Kishi, H. Nagura, S. Inagi, and T. Fuchigami Chem. Commun. 2008 3876
10. S. Fustero, S. Catalan, M. Sanchez-Rosello, A. Simon-Fuentes, and C. del Pozo Org. Lett. 12 2010 3484
11. S. Ye, J. Liu, and J. Wu Chem. Commun. 2012 5028
12. K.W. Bentley The Isoquinoline Alkaloids 1998 Hardwood Academic Amsterdam
13. T. Eicher, and S. Hauptmann The Chemistry of Heterocycles 2003 Wiley-VCH Weinheim
14. F. Dzierszinski, A. Coppin, M. Mortuaire, E. Dewally, C. Slomianny, J.-C. Ameisen, F. DeBels, and S. Tomavo Antimicrob. Agents Chemother. 46 2002 3197
15. L. Kong, C. Cheng, and R. Tan Planta Med. 67 2001 74
16. R. Davis, A. Carroll, G. Pierens, and R. Quinn J. Nat. Prod. 62 1999 419
17. E. Marco, W. Laine, C. Tardy, A. Lansiaux, M. Iwao, F. Ishibashi, C. Bailly, and F. Gago J. Med. Chem. 48 2005 3796
18. For some reviews, see: K.C. Majumdar, P. Debnath, N. De, and B. Roy Curr. Org. Chem. 15 2011 1760
19. A.G. Montalban Heterocycl. Nat. Prod. Synth. 2011 299
20. Y. Yamamoto, I.D. Gridnev, N.T. Patil, and T. Jin Chem. Commun. 2009 5075
21. F. Fulop, and G. Bernath Curr. Org. Chem. 3 1999 1
22. For selected examples, see: H. Gao, and J. Zhang Adv. Synth. Catal. 351 2009 85
23. N. Asao, Y.S. Salprima, T. Nogami, and Y. Yamamoto Angew. Chem., Int. Ed. 44 2005 5526
24. Q. Huang, and R.C. Larock J. Org. Chem. 68 2003 980
25. For selected examples, see: M. Balasubramanian, and J.G. Keay Isoquinoline Synthesis A.E. McKillop, A.R. Katrizky, C.W. Rees, E.F.V. Scrivem, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Elsevier Oxford 245 300
26. For a review on the synthesis of isoquinoline alkaloid, see: M. Chrzanowska, and M.D. Rozwadowska Chem. Rev. 104 2004 3341
27. S. Roy, B. Neuenswander, D. Hill, and R.C. Larock J. Comb. Chem. 11 2009 1061 and references cited therein
28. For some recent patents involving fluorinated isoquinolines, see: (a) Yamada, R.; Seto, M. U.S. Patent 201,093,789, 2010.
29. (b) Zeng, Q.; Yuan, C. C.; Yao, G.; Wang, X.; Tadesse, S.; Jean, D. J. S. Jr.; Reichelt, A.; Liu, Q.; Hong, F.-T.; Han, N.; Fotsch, C.; Davis, C.; Bourbeau, M. P. K.; Ashton, S.; Allen, J. G. WO 201,083,246, 2010.
30. (c) Matsubara, K.; Iesato, A.; Oomura, A.; Kawasaki, K.; Yamada, R.; Seto, M. U.S. Patent 200,948,223 A1, 2009.
31. T. Xu, and G. Liu Org. Lett. 14 2012 5416
32. Q. Xiao, J. Sheng, Q. Ding, and J. Wu Eur. J. Org. Chem. 2014 217
33. C. Si, and A.G. Myers Angew. Chem., Int. Ed. 50 2011 10409
34. Q. Liu, Y. Wu, P. Chen, and G. Liu Org. Lett. 15 2013 6210
35. For the selected reviews, see: M. Shimizu, and T. Hiyama Angew. Chem., Int. Ed. 44 2005 214
36. M. Schlosser Angew. Chem., Int. Ed. 45 2006 5432
37. O.A. Tomashenko, and V.V. Grushin Chem. Rev. 111 2011 4475
38. T. Furuya, A.S. Kamlet, and T. Ritter Nature 473 2011 470
39. T. Besset, C. Schneider, and D. Cahard Angew. Chem., Int. Ed. 51 2012 5048
40. A. Studer Angew. Chem., Int. Ed. 51 2012 8950
41. T. Liang, C. Neumann, and T. Ritter Angew. Chem., Int. Ed. 52 2013 8214
42. For the selected examples, see: Q. Huang, and R.C. Larock J. Org. Chem. 68 2003 980
43. G. Dai, and R.C. Larock J. Org. Chem. 68 2003 920
44. G. Dai, and R.C. Larock J. Org. Chem. 67 2002 7042
45. Q. Huang, J.A. Hunter, and R.C. Larock J. Org. Chem. 67 2002 3437
46. K.R. Roesch, and R.C. Larock J. Org. Chem. 67 2002 86
47. K.R. Roesch, H. Zhang, and R.C. Larock J. Org. Chem. 66 2001 8042
48. K.R. Roesch, and R.C. Larock Org. Lett. 1 1999 553
49. G. Dai, and R.C. Larock Org. Lett. 3 2001 4035
50. G.X. Dai, and R.C. Larock Org. Lett. 4 2002 193
51. H. Nakamura, H. Saito, and M. Nanjo Tetrahedron Lett. 49 2008 2697
52. N. Asao, S. Yudha, T. Nogami, and Y. Yamamoto Angew. Chem., Int. Ed. 44 2005 5526
53. N. Asao, K. Iso, and S. Yudha Org. Lett. 8 2006 4149
54. J. Jayakumar, K. Parthasarathy, and C.-H. Cheng Angew. Chem., Int. Ed. 51 2012 12343
55. G. Qiu, X. Qiu, and J. Wu Adv. Synth. Catal. 355 2013 3205