Three-component one-pot process to propargylic amines and related amide and sulfonamide compounds: application to the construction of 2-(aminomethyl)benzofurans and indoles

Tetrahedron

Volumn 63, Issue 43, 2007, Pages 10671-10683

  Russo, Olivier ^a   Messaoudi, Samir ^a,b   Hamze, Abdallah ^a,b   Olivi, Nathanäel ^b   Peyrat, Jean François ^a,b   Brion, Jean Daniel ^a,b   Sicsic, Sames ^a,b   Berque Bestel, Isabelle ^a,c   Alami, Mouâd ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

^c INSERM U869   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 (AMINOMETHYL)BENZOFURAN DERIVATIVE; 2 (AMINOMETHYL)BENZO[B]FURAN; AMIDE; AMINE; BENZOFURAN DERIVATIVE; DI TERT BUTYLIMINODICARBONATE; HALIDE; INDOLE DERIVATIVE; PHTHALIMIDE; PHTHALIMIDE POTASSIUM; PROPARGYL HALIDE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DEPROTECTION REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 34548480983     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.096     Document Type: Article

References (62)

1. Shirota F.N., DeMaster E.G., and Nagasawa H.T. J. Med. Chem. 22 (1979) 463-464
2. Yu P.H., Davies B.A., and Boulton A.A. J. Med. Chem. 35 (1992) 3705-3713
3. Connolly P.J., Wetter S.K., Beers K.N., Hamel S.C., Chen R.H.K., Wachter M.P., Ansell J., Singer M.M., Steber M., Ritchie D.M., and Argentieri D.C. Bioorg. Med. Chem. Lett. 9 (1999) 979-984
4. Corriu R.J.P., Bolin G., and Moreau J.J.E. Tetrahedron Lett. 32 (1991) 4121-4124
5. Campi E.M., Jackson W.R., and Nilsson Y. Tetrahedron Lett. 32 (1991) 1093-1094
6. Mandai T., Ryoden K., Kawada M., and Tsuji J. Tetrahedron Lett. 32 (1991) 7683-7686
7. Clive D.L.J., Cole D.C., and Tao Y. J. Org. Chem. 59 (1994) 1396-1406
8. Ripin D.H.B., Bourassa D.E., Brandt T., Castaldi M.J., Frost H.N., Hawkins J., Johnson P.J., Massett S.S., Neumann K., Phillips J., Raggon J.W., Rose P.R., Rutherford J.L., Sitter B., Stewart III A.M., Vetelino M.G., and Wei L. Org. Process Res. Dev. 9 (2005) 440-450
9. Hertner F.W., Hsiao Y., Eng K.K., Rivera N.R., Palucki M., Tan L., Yasuda N., Hughes D.L., Weissman S., Zewge D., King T., Tschaen D., and Volante R.P. J. Org. Chem. 69 (2004) 8723-8730
10. Kopka I.E., Fataftah Z., and Rathke M.W. J. Org. Chem. 45 (1980) 4616-4622
11. Imada Y., Yuassa M., Nakamura I., and Murahashi S.I. J. Org. Chem. 59 (1994) 2282-2284
12. Czernecki S., and Valery J.M. J. Carbohydr. Chem. 9 (1990) 767-770
13. Basak A., and Rudra K.R. Tetrahedron Lett. 41 (2000) 7231-7234
14. Basak A., and Shain J.C. Tetrahedron Lett. 39 (1998) 3029-3030
15. Glase S.A., Akunne H.C., Heffner T.G., Jaen J.C., Mackenzie R.G., Meltzer L.T., Pudsley T.A., Smith S.J., and Wise L.D. J. Med. Chem. 39 (1996) 3179-3187
16. Mahrwald R., and Quint S. Tetrahedron Lett. 42 (2001) 1655-1656
17. Fisher C., and Carreira E.M. Org. Lett. 3 (2001) 4319-4321
18. Wie C., and Li C.J. J. Am. Chem. Soc. 124 (2002) 5638-5639
19. Jiang B., and Si Y.G. Tetrahedron Lett. 44 (2003) 6767-6768
20. Díez R., Badorrey R., Díaz-de-Villegas M.D., and Gálvez J.A. Eur. J. Org. Chem. (2007) 2114-2120
21. Mladenova M., Alami M., and Linstrumelle G. Synth. Commun. 25 (1995) 1401-1410
22. Bleicher L.S., Cosford N.D.P., Herbaut A., Mc Callum J.S., and Mc Donald I.A. J. Org. Chem. 63 (1998) 1109-1118
23. Lemhadri M., Doucet H., and Santelli M. Synthesis (2005) 1359-1367
24. Tramontini M. Synthesis (1973) 703-775
25. Li C.J., and Wei C. Chem. Commun. (2002) 268-269
26. Wie C., Li Z., and Li C. J. Org. Lett. 5 (2003) 4473-4475
27. Wie C., and Li C. J. Am. Chem. Soc. 125 (2003) 9584-9585
28. Kabalka G.W., Venkataiah B., and Dong G. Tetrahedron Lett. 45 (2004) 729-731
29. Lo V.K.-Y., Liu Y., Wong M.K., and Che C.-M. Org. Lett. 8 (2006) 1529-1532
30. Aschwanden P., Stephenson C.R.J., and Carreira E.M. Org. Lett. 8 (2006) 2437-2440
31. Kwatra M.M., Simon D.Z., Salvador R.L., and Cooper P.D. J. Med. Chem. 21 (1978) 253-257
32. Olivi N., Spruyt P., Peyrat J.-F., Alami M., and Brion J.-D. Tetrahedron Lett. 45 (2004) 2607-2610
33. Russo O., Alami M., Brion J.-D., Sicsic S., and Berque-Bestel I. Tetrahedron Lett. 45 (2004) 7069-7072
34. Youngman M.A., and Dax S.L. J. Comb. Chem. 3 (2001) 469-472
35. For the multicomponent synthesis of heterocycles, see for instance:
36. Braun R.U., and Müller T.J.J. Synthesis (2004) 2391-2406
37. Braun R.U., Zeitler K., and Müller T.J.J. Org. Lett. 3 (2001) 3297-3300
38. Wyatt P.G., Allen M.J., Chilcott J., Gardner C.J., Livermore D.G., Mordaunt J.E., Nerozzi F., Patel M., Perren M.J., Weingarten G.G., Shabbir S., Woollard P.M., and Zhou P. Bioorg. Med. Chem. Lett. 12 (2002) 1405-1411
39. Kessler A., Faure H., Petrel C., Ruat M., Dauban P., and Dodd R.H. Bioorg. Med. Chem. Lett. 14 (2004) 3345-3349
40. Mustafa S.M., Bavadekar S.A., Ma G., Moore B.M., Feller D.R., and Miller D.D. Bioorg. Med. Chem. Lett. 15 (2005) 2758-2760
41. Alami M., Ferri F., and Linstrumelle G. Tetrahedron Lett. 34 (1993) 6403-6406
42. Unroe M.R., and Reinhardt B.A. Synthesis (1987) 981-985
43. Alami M., Peyrat J.-F., and Brion J.-D. Synthesis (2000) 1499-1518
44. Alami M., and Linstrumelle G. Tetrahedron Lett. 32 (1991) 6109-6112
45. Alami M., Ferri F., and Gaslain Y. Tetrahedron Lett. 37 (1996) 57-58
46. Alami M., Crousse B., and Ferri F. J. Organomet. Chem. 624 (2001) 114-123
47. Alami M., Peyrat J.-F., and Brion J.-D. Tetrahedron Lett. 43 (2002) 3007-3009 and references cited therein
48. Hashmi A.S.K., Haufe P., Rivas N.A., and Bats J.W. Adv. Synth. Catal. 346 (2004) 421-424
49. Denton T.T., Zhang X., and Cashman J.R. J. Med. Chem. 48 (2005) 224-239
50. Kitbunnadaj R., Zuiderveld O.P., De Esch I.J., Vollinga R.C., Bakker R., Lutz M., Spek A.L., Cavoy E., Deltent M.F., Menge W.M., Timmerman H., and Leurs R. J. Med. Chem. 46 (2003) 5445-5457
51. Hernandez J.N., Ramirez M.A., and Martin V.S. J. Org. Chem. 68 (2003) 743-746
52. Berque-Bestel I., Soulier J.L., Giner M., Rivail L., Langlois M., and Sicsic S. J. Med. Chem. 46 (2003) 2606-2620
53. Hilt G., and Galbiati F. Synlett (2005) 829-833
54. Nilsson B.M., Ringdahl B., and Hacksell U. J. Med. Chem. 33 (1990) 580-584
55. Youseung, K.; Soon bang, K.; Gyochang, K.; Min Seok, J.; Jae Yang, K.; Dae Yong, J. U.S. Pat. Appl. Publ. 2003, 119,880, 26 June 2003.
56. Seefeld M.A., Miller W.H., Newlander K.A., Burgess W.J., Payne D.J., Rittenhouse S.F., Moore T.D., DeWolf W.E., Keller P.M., Qiu X., Janson C.A., Vaidya K., Fosberry A.P., Smyth M.G., Joworski D.D., Slatter-Radosti C., and Huffman W.F. Bioorg. Med. Chem. Lett. 11 (2001) 2241-2244
57. Kabalka G.W., Wang L., and Pagni R.M. Tetrahedron Lett. 42 (2001) 6049-6051
58. Zhang H.-C., Brumfield K.K., Jaroskova L., and Maryanoff B.E. Tetrahedron Lett. 39 (1998) 4449-4452
59. For reviews, see:
60. Humphrey G.R., and Kuethe J.T. Chem. Rev. 106 (2006) 2857-2911
61. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873-2920
62. Cacchi S., Fabrizi G., and Goggiomani A. Heterocycles 56 (2001) 613-632