An iodoacetamide-based free radical cyclisation approach to the 7,12-dihydro-indolo[3,2- d][1]benzazepin-6(5 H)-one (paullone) system

A potentially versatile route to 2-(2-aminoaryl)indoles is described based on a palladium-mediated cyclisation of N-substituted indoles, together with free radical cyclisation of their N-benzyliodoacetamide derivatives to the 7,12-dihydro-indolo[3,2- d][1]benzazepin-6(5 H)-one system. Graphical Abst...

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Bibliographic Details
Published inTetrahedron Vol. 61; no. 23; pp. 5489 - 5498
Main Authors Bremner, John B., Sengpracha, Waya
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.06.2005
Elsevier
Subjects
7-Membered ring
Chemistry
Chemistry, Organic
Indolobenzazepinones
Iodoacetamides
Physical Sciences
Radical cyclisation
Science & Technology
Radical cyclisation
7-Membered ring
Indolobenzazepinones
Iodoacetamides
indolobenzazepinones
INHIBITORS
7-membered ring
radical cyclisation
lodoacetamides
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Summary:A potentially versatile route to 2-(2-aminoaryl)indoles is described based on a palladium-mediated cyclisation of N-substituted indoles, together with free radical cyclisation of their N-benzyliodoacetamide derivatives to the 7,12-dihydro-indolo[3,2- d][1]benzazepin-6(5 H)-one system. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.03.133