Synthesis of 4-substituted azepino[3,4-b]indole-1,5-diones
✍ Scribed by Julien Perron; Benoı̂t Joseph; Jean-Yves Mérour
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 213 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
✦ Synopsis
Monoor dibromo derivatives 2 and 3 were prepared by an efficient two-step route from 10-methyl-azepino [3,4-b]indole-1,5dione 1. Elimination reaction on 2 gave access to 4-bromo-10-methyl-2H,10H-azepino[3,4-b]indole-1,5-diones 4. Finally, 4-substituted 10methyl-2H,10H-azepino [3,4-b]indole-1,5-diones 6 -14 were synthesised in good yields from 4 via palladium-mediated cross-coupling reactions.
📜 SIMILAR VOLUMES
## 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 previo
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.