RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2002(10): 1351-1354
DOI: 10.1055/s-2002-33105
DOI: 10.1055/s-2002-33105
PAPER
© Georg Thieme Verlag Stuttgart · New York
Indoles as Nucleophiles in a Self-Catalytic Michael Reaction
Weitere Informationen
Received
27 February 2002
Publikationsdatum:
01. August 2002 (online)
Publikationsverlauf
Publikationsdatum:
01. August 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200210/lookinside/thumbnails/10.1055-s-2002-33105-1.jpg)
Abstract
C-3 Substituted indoles 7a-c were regioselectively synthesized in high yields by reacting indole 2 and electron-rich indoles 3,4 with acrylate 1. Additions of electron-deficient indoles 5,6 to the acrylate 1 gave N-substituted indoles 9a,b.
Key words
indoles - Michael reaction - regioselectivity - phosphonic acids
- 1
Houlihan WJ. In Indoles Vol. 1: Wiley; New York: 1972. - 2
Sundberg RJ. In Indoles Academic Press; London: 1996. - 3
Iqbal Z.Jackson AH.Rao KRN. Tetrahedron Lett. 1988, 29: 2577 - 4
Dujardin G.Poirier J.-M. Bull. Soc. Chim. Fr. 1994, 131: 900 - 5
Harrington PE.Kerr MA. Synlett 1996, 1047 - 6
Harrington P.Kerr MA. Can. J. Chem. 1998, 76: 1256 - 7
Krawczyk H. Synlett 1998, 1114 - 8
Krawczyk H. Synth. Commun. 2000, 30: 1787 - 9
Krawczyk H.Bodalski R. J. Chem. Soc., Perkin Trans. 1 2001, 1559 - 10
Gavuzzo E.Pochetti G.Mazza F.Gallina C.Gorini B.D’Alessio S.Pieper M.Tschesche H.Tucker PA. J. Med. Chem. 2000, 43: 3377 - 11
Lavielle G.Hautefaye P.Schaeffer C.Boutin JA.Cudennec CA.Pierrè A. J. Med. Chem. 1991, 34: 1998 - 12
Chen SF.Kumar SD.Tishler M. Tetrahedron Lett. 1983, 24: 5461 - 13
Subotkowski W.Kowalik J.Tyka R.Mastalerz P. Pol. J. Chem. 1981, 55: 853