Convenient synthesis of tryptophols and tryptophol homologues by hydroamination of alkynes

Tetrahedron

Volumn 61, Issue 32, 2005, Pages 7622-7631

  Khedkar, Vivek ^a   Tillack, Annegret ^a   Michalik, Manfred ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Amination; Catalysis; Indoles

Indexed keywords

2 (1,2 DIMETHYL 1H INDOL 3 YL)ETHANOL; 2 (5 CHLORO 2 METHYL 1H INDOL 3 YL)ETHANOL; 2 (N BENZYL 2 METHYL 1H INDOL 3 YL)ETHANOL; 2 (N BENZYL 4 CHLORO 5 FLUORO 2 METHYL 1H INDOL 3 YL)ETHANOL; 2 (N BENZYL 4,5 DICHLORO 2 METHYL 1H INDOL 3 YL)ETHANOL; 2 (N BENZYL 5 FLUORO 2 METHYL 1H INDOL 3 YL)ETHANOL; 2 (N BENZYL 5 METHOXY 2 METHYL 1H INDOL 3 YL)ETHANOL; 2 (N BENZYL 5,6 DICHLORO 2 METHYL 1H INDOL 3 YL)ETHANOL; 2 (N BENZYL 6 CHLORO 5 FLUORO 2 METHYL 1H INDOL 3 YL)ETHANOL; 3 (1,2 DIMETHYL 1H INDOL 3 YL)PROPANOL; 3 (1,2,3 TRIMETHYL 1H INDOL 3 YL)PROPANOL; 3 (N BENZYL 2 METHYL 1H INDOL 3 YL)PROPANOL; 3 (N BENZYL 4 CHLORO 1H INDOL 3 YL)PROPANOL; 3 (N BENZYL 4,5 DICHLORO 1H INDOL 3 YL)PROPANOL; 3 (N BENZYL 5,6 DICHLORO 1H INDOL 3 YL)PROPANOL; 3 (N BENZYL 6 CHLORO 1H INDOL 3 YL)PROPANOL; 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 1,2 DIMETHYL 1H INDOLE; 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 5 CHLORO 1,2 DIMETHYL 1H INDOLE; 3 [3 (TERT BUTYLDIMETHYLSILYLOXY)PROPYL] 1,2 DIMETHYL 1H INDOLE; ALKYNE DERIVATIVE; N BENZYL 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 2 METHYL 1H INDOLE; N BENZYL 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 4 CHLORO 5 FLUORO 2 METHYL 1H INDOLE; N BENZYL 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 4,5 DICHLORO 2 METHYL 1H INDOLE; N BENZYL 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 5 METHOXY 2 METHYL 1H INDOLE; N BENZYL 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 5,6 DICHLORO 2 METHYL 1H INDOLE; N BENZYL 3 [2 (TERT BUTYLDIMETHYLSILYLOXY)ETHYL] 6 CHLORO 5 FLUORO 2 METHYL 1H INDOLE; N BENZYL 3 [3 (TERT BUTYLDIMETHYLSILYLOXY)PROPYL] 2 DIMETHYL 1H INDOLE; N BENZYL 3 [3 (TERT BUTYLDIMETHYLSILYLOXY)PROPYL] 3 CHLORO 2 METHYL 1H INDOLE; N BENZYL 3 [3 (TERT BUTYLDIMETHYLSILYLOXY)PROPYL] 3 DICHLORO 2 METHYL 1H INDOLE; TRYPTOPHOL; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 21844435769     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.093     Document Type: Article

References (57)

1. K.B. Hong, C.W. Lee, and E.K. Yum Tetrahedron Lett. 45 2004 693 697
2. P. Köhling, A.M. Schmidt, and P. Eilbracht Org. Lett. 5 2003 3213 3216
3. S. Cacchi, G. Fabrizi, and L.M. Parisi Org. Lett. 5 2003 3843 3846
4. H. Siebeneicher, I. Bytschkov, and S. Doye Angew. Chem., Int. Ed. 42 2003 3042 3044
5. K. Onitsuka, S. Suzuki, and S. Takahashi Tetrahedron Lett. 43 2002 6197 6199
6. J.F. Rutherford, M.P. Rainka, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 15168 15169
7. M. Tokunaga, M. Ota, M. Haga, and Y. Wakatsuki Tetrahedron Lett. 42 2001 3865 3868
8. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045 1075
9. G. Verspui, G. Elbertse, F.A. Sheldon, M.A.P.J. Hacking, and R.A. Sheldon Chem. Commun. 2000 1363 1364
10. M. Beller, C. Breindl, T.H. Riermeier, M. Eichberger, and H. Trauthwein Angew. Chem., Int. Ed. 37 1998 3389 3391
11. A. Moballigh, R. Jackstell, and M. Beller Tetrahedron Lett. 45 2004 869 873
12. K. Kumar, A. Zapf, D. Michalik, A. Tillack, M. Arlt, and M. Beller Org. Lett. 6 2004 7 10
13. A. Tillack, H. Jiao, I. Garcia Castro, C.G. Hartung, and M. Beller Chem. Eur. J. 10 2004 2409 2420
14. V. Khedkar, A. Tillack, M. Michalik, and M. Beller Tetrahedron Lett. 45 2004 3123 3126
15. see also (b) C. Cao, Y. Shi, and A.L. Odom Org. Lett. 4 2002 2853 2856
16. P.G. Mantle, and C.M. Weedon Phytochemistry 36 1994 1209 1218
17. D.A. Martens, and W.T. Frankenberger J. Soil Sci. 155 1993 263 271
18. M. Shin, T. Shinguu, K. Sano, and C. Umezawa Chem. Pharm. Bull. 39 1991 1792 1795
19. F. Sugawara, and G.A. Strobel Phytochemistry 26 1987 1349 1352
20. W.A. Ayer, L.M. Browne, M.-C. Feng, H. Orszanska, and H. Saeedi-Ghomi Can. J. Chem. 64 1986 904 909
21. (f) Kawashima, A.; Seto, H.; Kato, M.; Yasuda, A.; Uchida, K.; Otake, N. J. Antibiot. 1986, 39, 1495-1497;
22. Chem. Abstr. 1986, 106, 29752q.
23. G. Lacan, V. Magnus, S. Simaga, S. Iskric, and P.J. Hall Plant Physiol. 78 1985 447 454
24. P. Fenn, R.D. Durbin, and J.E. Kuntz Phytochemistry 16 1977 899 901
25. (i) Ehrlich, F. Ber. 1909, 45, 883-889;
26. Chem. Abstr. 1909, 6, 24272.
27. P. Vincendeau, S. Lesthelle, A. Bertazzo, M.C. Okomo-Assoumou, G. Allegri, and C.V. Costa Adv. Exp. Med. Biol. 467 1999 525 531
28. E.M. Cornford, P.D. Crane, L.D. Braun, W.D. Bocash, A.M. Nyerges, and W.H. Oldendorf J. Neurochem. 36 1981 1758 1765
29. I.N. Fernando, P.L. Francis, and I. Smith J. Neural. Transm. 56 1983 33 41
30. L.G. Humber, E. Ferdinandi, C.A. Demerson, S. Ahmed, U. Shah, D. Mobilio, J. Sabatucci, B.D. Lange, F. Labbadia, P. Hughes, J.D. Virgilio, G. Neuman, T.T. Chau, and B.M. Weichman J. Med. Chem. 31 1988 1712 1719
31. T.T. Chau, T. Walter, A. Katz, and B.M. Weichman Drug Dev. Res. 28 1993 488 495
32. A.H. Katz, C.A. Demerson, C.C. Shaw, A.A. Asselin, L.G. Humber, K.M. Conway, G. Gavin, C. Guinosso, N.P. Jensen, D. Mobilio, R. Noureldin, J. Schmid, U. Shah, D.V. Engen, T.T. Chau, and B.M. Weichman J. Med. Chem. 31 1988 1244 1250
33. S.J. Garden, R.B. Da Silva, and A.C. Pinto Tetrahedron 58 2002 8399 8412
34. S. Wagaw, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 121 1999 10251 10263
35. S. Wagaw, B.H. Yang, and S.L. Buchwald J. Am. Chem. Soc. 120 1998 6621 6622
36. Y. Dong, and C.A. Busacca J. Org. Chem. 62 1997 984 990
37. D. Zhang, and L.S. Liebeskind J. Org. Chem. 61 1996 6464 6465
38. M. Amat, M.D. Coll, D. Passarella, and J. Bosch Tetrahedron: Asymmetry 7 1996 3091 3094
39. (g) Johnson, H. E. US Patent 3,197,479, 27 July, 1965; Chem. Abstr. 1965, 63, P13217f.
40. H. Kotsuki, K. Hayaschida, T. Shimanouchi, and H. Nishizawa J. Org. Chem. 61 1996 984 990
41. H. Kotsuki, M. Teraguchi, N. Shimomoto, and M. Ochi Tetrahedron Lett. 37 1996 3727 3730
42. A. Ghosh, W. Wang, J.P. Freeman, J.S. Althaus, P.F. Von Voigtlander, T.A. Scahill, S.A. Mizsak, and J. Szmuszkovicz Tetrahedron 47 1991 8653 8662
43. R.M. Soll, C. Guinosso, and A. Asselin J. Org. Chem. 53 1988 2844 2847
44. Y. Ito, K. Kobayaschi, N. Seko, and T. Saegusa Bull. Chem. Soc. Jpn. 57 1984 73 84
45. C.A. Demerson, L.G. Humber, A.H. Philip, and R.R. Martel J. Med. Chem. 19 1976 391 395
46. J. Bergman Tetrahedron 27 1971 1167 1171
47. G. Tacconi Farmaco Ed. Sci. 20 1965 891 901
48. B. Robinson The Fischer Indole Synthesis 1982 Wiley Chichester
49. D.L. Hughes Org. Prep. Proced. Int. 25 1993 607 623
50. K.R. Campos, J.C.S. Woo, S. Lee, and R.D. Tillyer Org. Lett. 6 2004 79 82
51. A. Tillack, V. Khedkar, and M. Beller Tetrahedron Lett. 45 2004 8875 8878
52. A.W. Duff, R.A. Kamarudin, M.F. Lappert, and R.J. Norton J. Chem. Soc., Dalton Trans. 1986 489 498
53. V. Khedkar, A. Tillack, and M. Beller Org. Lett. 5 2003 4767 4770
54. For a recent review on Markovnikov and anti-Markovnikov functionalization of olefins and alkynes see: J. Seayad, A. Tillack, H. Jiao, and M. Beller Angew. Chem., Int. Ed. 43 2004 3368 3398
55. B.B. Snider, and Z. Shi J. Am. Chem. Soc. 116 1994 549 557
56. I.I. Grandberg, and G.P. Tokmakov Khim. Geterotsikl. Soedin. 2 1974 204
57. L.B. Dmitriev, and I.I. Grandberg Khim. Geterotsikl. Soedin. 7 1975 946