Synthesis of Substituted Azepino[3,4-b]indole-1,5-diones
✍ Scribed by Julien Perron; Benoît Joseph; Jean-Yves Mérour
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 164 KB
- Volume
- 2004
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
Cyclic β‐amino esters 4, obtained from lactams, were condensed with indole‐2‐carbonyl chloride to afford the corresponding amides. Similarly, unusual conditions led to cyclisation at the 3‐position of the indole moiety in the presence of __p__TSA and ethylene glycol to afford previously unknown pentacyclic derivatives 12 and 15. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
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Preparation of the 5-substituted azepino [3,4-b]indole core structure can be realised through a catalytic Heck reaction. The scope and limitations of this methodology are reported. The reactivity of di-tert-butyl 5ethoxycarbonylmethylene-1,3,4,5-tetrahydro-1-oxoazepino[3,4-b]indole-2,10-dicarboxylat
## Abstract 3‐Amino‐4‐(3‐indolyl)pyrrolin‐2,5‐diones are condensed with various aldehydes and ketones to the cor responding imines. Under Pictet‐Spengler conditions, the latter do not cyclize to pyrrolo‐β‐carbolines, but readily yield pyrrolo[3′,4′:2,3]azepino[4,5,6‐__cd__]indole‐8,10‐diones.