Synthesis of novel indole derivatives: Variations in the Bartoli reaction

Synlett

Volumn , Issue 10, 1999, Pages 1594-1596

  Dobbs, Adrian P ^a,b   Voyle, Martyn ^a   Whittall, Neil ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

^b OPEN UNIVERSITY   (United Kingdom)

Author keywords

Bartoli reaction; Grignard reactions; Indoles; Regioselectivity

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0032848528     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2900     Document Type: Article

References (18)

1. For example see: a) Palladium catalysed aryl halide/acetylene coupling and base promoted cyclisation: Kondo, Y., Kojima, S., Sakamoto, T. Heterocycles 1996, 43, 2741-2746; Kondo, Y., Kojima, S., Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511;
2. For example see: a) Palladium catalysed aryl halide/acetylene coupling and base promoted cyclisation: Kondo, Y., Kojima, S., Sakamoto, T. Heterocycles 1996, 43, 2741-2746; Kondo, Y., Kojima, S., Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511;
3. b) Palladium mediated coupling and cyclisation reactions of aryl halides with acetylenes: Ezquerra, J., Pedregal, C., Lamas, C., Barluenga, J., Pérez, M., García-Martín, M. A., González, J. M. J. Org. Chem. 1996, 61, 5804-5812; Rudisill, D. E., Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866;
4. b) Palladium mediated coupling and cyclisation reactions of aryl halides with acetylenes: Ezquerra, J., Pedregal, C., Lamas, C., Barluenga, J., Pérez, M., García-Martín, M. A., González, J. M. J. Org. Chem. 1996, 61, 5804-5812; Rudisill, D. E., Stille, J. K. J. Org. Chem. 1989, 54, 5856-5866;
5. c) Palladium catalysed couplings with boranes: Satoh, M., Miyaura, N., Suzuki, A. Synthesis 1987, 373-377;
6. d) Via palladium catalysed annulations between iodoaniline and ketones: Chen, C.-Y., Lieberman, D.R., Larsen, R.D., Verhoeven, T.R., Reider, P.J. J. Org. Chem. 1997, 62, 2676-2677;
7. e) Via Heck-type reactions: Kasahara, A., Izumi, T., Kikuchi, T., Xiao-ping, L. J. Heterocyclic Chem. 1987, 24, 1555-1556.
8. a) Bartoli, G., Palmieri, G., Bosco, M., Dalpozzo, R. Tetrahedron Lett. 1989, 30, 2129-2132;
9. b) Bartoli, G., Bosco, M., Dalpozzo, R., Palmieri, G., Marcantoni, E. J. Chem. Soc. Perkin Trans. I 1991, 2757-2761;
10. c) Bosco, M., Dalpozzo, R., Bartoli, G., Palmieri, G., Petrini, M. J. Chem. Soc. Perkin Trans.II 1991, 657-663;
11. d) Dobson, D., Todd, A., Gilmore, J. Synth. Commun. 1991, 21, 611-617;
12. e) Dobson, D., Todd, A., Gilmore, J. Synlett 1992, 79-80
13. Giacomoni, J.C., Cambon, A., Rouvier, E. Bull. Soc. Chim. France 1970, 3097-3098 (bromination) and Bandodakar, B.S., Nagendrappa, G. Synthesis 1990, 843-844 (elimination).
14. Giacomoni, J.C., Cambon, A., Rouvier, E. Bull. Soc. Chim. France 1970, 3097-3098 (bromination) and Bandodakar, B.S., Nagendrappa, G. Synthesis 1990, 843-844 (elimination).
15. C (assignment). Coupling constants (J values) are quoted to one decimal place with values in Hz. Mass spectra were recorded on a HP-5890GC-VG-Masslab Trio-2 gas chromatography-mass spectrometer.
16. 3), 6.90 (1H, d, J 7.1, C(5)H), 7.00 (1H, dd, J 7.3, C(6)H), 7.32 (1H, d, J 7.5, C(4)H).
17. Laird, T. Org. Proc. Res. Dev. 1998, 2, 210-213; Beck, C.M., Park, Y.-J., Crabtree, R.H. J. C. S. Chem. Commun. 1998, 693-694 and reference therein.
18. Laird, T. Org. Proc. Res. Dev. 1998, 2, 210-213; Beck, C.M., Park, Y.-J., Crabtree, R.H. J. C. S. Chem. Commun. 1998, 693-694 and reference therein.