p-Toluenesulfonic acid-promoted selective functionalization of unsymmetrical arylalkynes: a regioselective access to various arylketones and heterocycles

Tetrahedron

Volumn 66, Issue 21, 2010, Pages 3775-3787

  Jacubert, Maud ^a   Provot, Olivier ^a   Peyrat, Jean François ^a   Hamze, Abdallah ^a   Brion, Jean Daniel ^a   Alami, Mouâd ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Alkynes; Benzofuran; Benzothiophene; Cyclization; Hydration; Ketone; p Toluenesulfonic acid

Indexed keywords

1 (2 (2 METHOXYPHENYL)ETHYNYL)NAPHTHALENE; 1 (2 METHOXYPHENYL) 4 (4 METHOXYPHENYL)BUTA 1,3 DIYNE; 1 (4 (2 METHOXYPHENYL)BUTA 1,3 DIYNYL)NAPHTHALENE; 1 (4 (DIPROP 2 YNYLAMINO)PHENYL) 3 ETHOXYPROPAN 1 ONE; 1 (4 AMINOPHENYL) 6 HYDROXYHEXAN 1 ONE; 1 (4 METHOXYPHENYL)HEXAN 1 ONE; 1 METHOXY 2 (4 PHENYLBUT 3 EN 1 YNYL)BENZENE; 1 METHOXY 2 (OCT 3 EN 1 YNYL)BENZENE; 2,4 DIMETHOXY 1 ((2 METHOXYPHENYL)ETHYNYL)BENZENE; 3 (2 HYDROXYETHOXY) 1 (4 METHOXYPHENYL)PROPAN 1 ONE; 3 ETHOXY 1 (4 METHOXYPHENYL)BUTAN 1 ONE; 3 ETHOXY 1 (4 METHOXYPHENYL)PROPAN 1 ONE; 3 HYDROXY 1 (4 METHOXYPHENYL)PROPAN 1 ONE; 3 ISOPROPOXY 1 (4 METHOXYPHENYL)PROPAN 1 ONE; 3 METHOXY 1 (2 METHOXYPHENYL)PROPAN 1 ONE; 4 (2 METHOXYPHENYL) 1 (4 METHOXYPHENYL)BUT 1 EN 3 YNE; 4 (4 TOLYLETHYNYL)BENZENAMINE; 4 ETHOXY 1 (4 METHOXYPHENYL)BUTAN 1 ONE; 5 ETHOXY 1 (4 METHOXYPHENYL)PENTAN 1 ONE; 5 HDYROXY 1 (4 METHOXYPHENYL)PENTAN 1 ONE; 6 HYDROXY 1 (4 METHOXYPHENYL)HEXAN 1 ONE; ALKYNE DERIVATIVE; KETONE DERIVATIVE; METHYL(2 (2 NAPHTHALEN 1 YL)ETHYNYL)PHENYL)SULFANE; METHYL(2 (4 PHENYLBUT 3 EN 1 YNYL)PHENYL)SULFANE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TERT BUTYL(2 ((2 METHOXYPHENYL)ETHYNYL)PHENOXY)DIMETHYL SILANE; TERT BUTYLDIMETHYL[2 [2 [2 (METHYLTHIO)PHENYL]ETHYNYL] PHENOXY]SILANE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CYCLIZATION; ETHERIFICATION; HYDRATION; MICROWAVE IRRADIATION; PRIORITY JOURNAL; REACTION TIME; SYNTHESIS;

EID: 77951294473     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.055     Document Type: Article

References (77)

1. For an excellent review, see:. Hintermann L., and Labonne A. Synthesis (2007) 1121
2. Kucherov M. Chem. Ber. 14 (1881) 1540
3. Marion N., Ramón R.S., and Nolan S.P. J. Am. Chem. Soc. 131 (2009) 448
4. Mizushima E., Sato K., Hayashi T., and Takana M. Angew. Chem., Int. Ed. 41 (2002) 4563
5. Casado R., Contel M., Laguna M., Romero P., and Sanz S. J. Am. Chem. Soc. 125 (2003) 11925
6. Tokunaga M., and Wakatsuki Y. Angew. Chem., Int. Ed. 37 (1998) 2867
7. Chen Y., Valentini M., Pregosin P.S., and Albinati A. Inorg. Chim. Acta 327 (2002) 4
8. Alvarez P., Gimeno J., Lastra E., García-Granda S., Van der Maelen J.F., and Bassetti M. Organometallics 20 (2001) 3762
9. Hirabayashi T., Okimoto Y., Saito A., Morita M., Sakaguchi S., and Ishii Y. Tetrahedron Lett. 62 (2006) 2231
10. Chin C.S., Chang W.-T., Yang S., and Joo K.-S. Bull. Korean Chem. Soc. 18 (1997) 324
11. Kanemitsu H., Uehara K., Fukuzumi S., and Ogo S. J. Am. Chem. Soc. 130 (2008) 17141
12. James B.R., and Rempel G.L. J. Am. Chem. Soc. 91 (1969) 863
13. Blum J., Huminer H., and Alper H. J. Mol. Catal. 75 (1992) 153
14. Baidossi W., Lahav M., and Blum J. J. Org. Chem. 62 (1997) 669
15. Israelsohn O., Vollhardt K.P.C., and Blum J. J. Mol. Catal. 184 (2002) 1
16. Hartman J.W., and Sperry L. Tetrahedron Lett. 45 (2004) 3787
17. Liu B., and De Brabander J.K. Org. Lett. 8 (2006) 4907
18. Boll M., Schink B., Messerschmidt A., and Kroneck P.M.H. Biol. Chem. 386 (2005) 999
19. Alipui O.D., Zhang D., and Schulz H. Biochem. Biophys. Res. Commun. 292 (2002) 1171
20. Wang S.C., Person M.D., Johnson W.H., and Whitman C.P. Biochemistry 42 (2003) 8762
21. Tsuchimoto T., Joya T., Shirakawa E., and Kawakami Y. Synlett (2000) 1777
22. Allen A.D., Chiang Y., Kresge A.J., and Tidwell T.T. J. Org. Chem. 47 (1982) 775 and references cited therein
23. Menash N., and Shvo Y. J. Org. Chem. 58 (1993) 7434
24. Alami M., and Ferri F. Synlett (1996) 755
25. Liron F., Le Garrec P., and Alami M. Synlett (1999) 246
26. Alami M., Liron F., Gervais M., Peyrat J.-F., and Brion J.-D. Angew. Chem., Int. Ed. 41 (2002) 1578
27. Hamze A., Provot O., Alami M., and Brion J.-D. Org. Lett. 7 (2005) 5625
28. Hamze A., Provot O., Brion J.-D., and Alami M. Synthesis (2007) 2025
29. Hamze A., Provot O., Brion J.-D., and Alami M. J. Org. Chem. 72 (2007) 3868
30. Giraud A., Provot O., Hamze A., Brion J.-D., and Alami M. Tetrahedron Lett. 49 (2008) 1107
31. Kwatra M.M., Simon D.Z., Salvador R.L., and Cooper P.D. J. Med. Chem. 21 (1978) 253
32. Olivi N., Thomas E., Peyrat J.-F., Alami M., and Brion J.-D. Synlett (2004) 2175
33. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467
34. Alami M., Ferri F., and Linstrumelle G. Tetrahedron Lett. 34 (1993) 6403
35. For a review see:. Swaminathan S., and Narayanan K.V. Chem. Rev. 71 (1971) 429
36. Tzalis D., Koradin C., and Knochel P. Tetrahedron Lett. 40 (1999) 6193
37. For a review, see:. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079
38. Thierney J.P., and Lidström P. Microwave Assisted Organic Synthesis (2005), Blackwell Publishing Ldt, Oxford
39. Caddick S. Tetrahedron 51 (1995) 10403
40. Perreux L., and Loupy A. Tetrahedron 57 (2001) 9199
41. Lisström P., Thierney J., Wathey B., and Westman J. Tetrahedron 57 (2001) 9225
42. Bekaert A., Provot O., Rasolojaona O., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron Lett. 46 (2005) 4187
43. Le Bras G., Provot O., Bekaert A., Peyrat J.-F., Alami M., and Brion J.-D. Synthesis (2006) 1537
44. L'Hermite N., Giraud A., Provot O., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron 62 (2006) 11994
45. Giraud A., Provot O., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron 62 (2006) 7667
46. Le Bras G., Provot O., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron Lett. 47 (2006) 5497
47. Le Bras G., Radanyi C., Peyrat J.-F., Brion J.-D., Alami M., Marsaud V., Stella B., and Renoir J.-M. J. Med. Chem. 50 (2007) 6189
48. Pettit G.R., Singh S.B., Niven M.L., Hamel E., and Schmidt J.M. J. Nat. Prod. 50 (1987) 119
49. Provot O., Giraud A., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron Lett. 46 (2005) 8547
50. Mousset C., Giraud A., Provot O., Hamze A., Bignon J., Liu J.-M., Thoret S., Dubois J., Brion J.-D., and Alami M. Bioorg. Med. Chem. Lett. 18 (2008) 3266
51. Hamze A., Giraud A., Messaoudi M., Provot O., Peyrat J.-F., Bignon J., Liu J.-M., Wdzieczak-Bakala J., Thoret S., Dubois J., Brion J.-D., and Alami M. ChemMedChem 4 (2009) 1912
52. Messaoudi S., Tréguier B., Hamze A., Provot O., Peyrat J.-F., Rodrigo De Losada J., Liu J.-M., Bignon J., Wdzieczak-Bakala J., Thoret S., Dubois J., Brion J.-D., and Alami M. J. Med. Chem. 52 (2009) 4538
53. Jacubert M., Hamze A., Provot O., Peyrat J.-F., Brion J.-D., and Alami M. Tetrahedron Lett. 50 (2009) 3588
54. For benzofuran derivatives, see for example:
55. Donnelly D.M.X., and Meegan M.J. In: Katritzky A.R. (Ed). Comprehensive Heterocyclic Chemistry Vol. 4 (1984), Pergamon, New York, NY
56. Bakunov S., Bakunova S., Wenzler T., Barszcz T., Werbovetz K., Brun R., and Tidwell R. J. Med. Chem. 51 (2008) 6927
57. McCallion G.D. Curr. Org. Chem. 3 (1999) 67 For benzothiphene derivatives see for example:
58. Palkowitz A.D., Glasebrook A.L., Thrascher K.J., Hauser K.L., Short L.L., Phillips D.L., Muehl B.S., Sato M., Shetler P.K., Cullinan G.J., Pell T.R., and Bryant H.U. J. Med. Chem. 40 (1997) 1407
59. Chen Z., Mocharla V.P., Farmer J.M., Pettit G.R., Hamel E., and Pinney K.G. J. Org. Chem. 65 (2000) 8811
60. Fournier Dit Chabert J.F., Joucla L., David E., and Lemaire M. Tetrahedron 60 (2004) 3221
61. Le Bras G., Hamze A., Messaoudi S., Provot O., Le Calvez P.-B., Brion J.-D., and Alami M. Synthesis (2008) 1607
62. Seck M., Franck X., Hocquemiller R., Figadère B., Peyrat J.-F., Provot O., Brion J.-D., and Alami M. Tetrahedron Lett. 45 (2004) 1881
63. Ramiandrasoa P., Bréhon B., Thivet A., Alami M., and Cahiez G. Tetrahedron Lett. 38 (1997) 2447
64. Peyrat J.-F., Thomas E., L'Hermite N., Alami M., and Brion J.-D. Tetrahedron Lett. 44 (2003) 6703
65. Alami M., and Ferri F. Tetrahedron Lett. 37 (1996) 2763
66. Byun J.H., Kim H., Kim Y., Mook-Jung I., Kim D.J., Lee W.L., and Yoo K.H. Bioorg. Med. Chem. Lett. 18 (2008) 5591
67. Hayakawa I., Shioya R., Agatsuma T., Furukawa H., Naruto S., and Sugano Y. Bioorg. Med. Chem. Lett. 14 (2004) 455
68. Yoo H., Lee L.Y., Park J.H., Chung B.Y., and Lee Y.S. Farmaco 58 (2003) 1243
69. Bietti M., and Capone A. J. Org. Chem. 73 (2008) 618
70. Atkinson R.S. J. Chem. Soc. C 4 (1971) 784
71. Commercially available
72. Park J.Y., Ullapu P.R., Choo H., Lee J.K., Min S.-J., Pae A.N., Kim Y., Baek D.-J., and Cho Y.S. Eur. J. Org. Chem. (2008) 5461
73. Duan X.-F., Zeng J., Zhang Z.-B., and Zi G.-F. J. Org. Chem. 72 (2007) 10283
74. Clerici A., and Porta O. J. Org. Chem. 55 (1990) 1240
75. Ohta A., Akita Y., Ohkuwa T., Chiba M., and Fukunaga R. Heterocycles 31 (1990) 1951
76. Macleod C., McKiernan G.J., Guthrie E.J., Farrugia L.J., Hamprecht D.W., Macritchie J., and Hartley R.C. J. Org. Chem. 68 (2003) 387
77. Bryan C.S., Braunger J.A., and Lautens M. Angew. Chem., Int. Ed. 48 (2009) 7064