A general procedure for the synthesis of 1,3-bis(indolyl) compounds via Michael addition catalyzed by InBr3/TMSCl

Synthesis

Volumn , Issue 3, 2003, Pages 397-402

  Bandini, Marco ^a   Fagioli, Matteo ^a   Melloni, Alfonso ^a   Umani Ronchi, Achille ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Catalysis; Enones; Indium; Indoles; Michael additions

Indexed keywords

ADDITION REACTIONS; CATALYSIS; KETONES; MIXTURES;

MICHAEL ADDITION;

SYNTHESIS (CHEMICAL);

1,3 BIS(INDOL 3 YL)BUTAN 1 ONE; BROMIDE; INDIUM; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; REPRODUCIBILITY; SYNTHESIS;

EID: 0037231051     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37359     Document Type: Article

References (23)

1. Zhao, S.; Liao, X.; Cook, J. M. Org. Lett. 2002, 4, 687; and references cited therein.
2. (a) Faulkner, D. J. J. Nat. Prod. Rep. 2001, 18, 1.
3. (b) Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2002, 4, 941.
4. (c) Jiang, B.; Yang, C.-G.; Wang, J. J. Org. Chem. 2002, 67, 1396.
5. Nenaidenko, V. G.; Baraznenok, I. L.; Balenkova, F. S. Russ. J. Org. Chem. 1998, 34, 1019.
6. (a) Bandini, M.; Cozzi, P. G.; Giacomini, M.; Melchiorre, P.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 3700.
7. (b) Bandini, M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. Synthesis 2002, 1110.
8. Okuachi, T.; Itonaga, M.; Minami, T.; Owa, T.; Kitoh, K.; Yoshino, H. Org. Lett. 2000, 2, 1485.
9. 3 as Lewis acids in organic transformations was first reported by Mukaiyama et al.: (a) Mukaiyama, T.; Ohno, T.; Han, J. S.; Kobayashi, S. Chem. Lett. 1991, 949. (b) Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han, S. J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1991, 64, 2524.
10. 3 as Lewis acids in organic transformations was first reported by Mukaiyama et al.: (a) Mukaiyama, T.; Ohno, T.; Han, J. S.; Kobayashi, S. Chem. Lett. 1991, 949. (b) Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han, S. J.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1991, 64, 2524.
11. For a discussion concerning the accelerating effects of trimethylsilyl halides in catalyzed conjugate additions, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. (b) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6019. (c) Pollock, P.; Dambacher, J.; Annes, R.; Brgdahl, M. Tetrahedron Lett. 2002, 43, 3639.
12. For a discussion concerning the accelerating effects of trimethylsilyl halides in catalyzed conjugate additions, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. (b) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6019. (c) Pollock, P.; Dambacher, J.; Annes, R.; Brgdahl, M. Tetrahedron Lett. 2002, 43, 3639.
13. For a discussion concerning the accelerating effects of trimethylsilyl halides in catalyzed conjugate additions, see: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015. (b) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6019. (c) Pollock, P.; Dambacher, J.; Annes, R.; Brgdahl, M. Tetrahedron Lett. 2002, 43, 3639.
14. 3/TMSCl (10 mol%) affording the corresponding 1,4-adduct in 18% and 72% yields, respectively. With N-methylpyrrole, the product was isolated as a 1:1 mixture of C-2/C-3 nucleophilic addition.
15. (a) Routier, S.; Saugé, L.; Ayerbe, N.; Couder, G.; Mérour, J.-Y. Tetrahedron Lett. 2002, 43, 589.
16. (b) Nettekoven,M.; Psiorz,M.; Waldmann,H. Tetrahedron Lett. 1995, 36, 1425.
17. 3: Lee, P. H.; Lee, K.; Sung, S.; Chang, S. J. Org. Chem. 2001, 66, 8646.
18. 2, r.t.) analysis of a 1a/TMSCl mixture.
19. Bandini, M.; Cozzi, P. G.; Garelli, A.; Melchiorre, P.; Umani-Ronchi, A. Eur. J. Org. Chem. 2002, 3243.
20. Onishi, Y.; Iko, T.; Yasuda, M.; Baba, A. Tetrahedron 2002, 58, 8227.
21. (a) de Koning, C. B.; Michael, J. P.; Rousseau, A. L. J. Chem. Soc., Perkin Trans. 1 2000, 1705.
22. (b) Vaillancourt, V.; Albizati, K. F. J. Am. Chem. Soc. 1993, 115, 3499.
23. (c) Mahboobi, S.; Teller, S.; Pongratz, H.; Hufsky, H.; Sellmer, A.; Botzki, A.; Uecker, A.; Beckers, T.; Baasner, S.; Schächtele, A.; Überall, F.; Kassack, M. U.; Dove, S.; Böhmer, F. J. Med. Chem. 2002, 45, 1200.