Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 31-32, Pages 5563-5571Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900798
Keywords
Quinolines; Spirocycles; Indolenines; Rearrangement; Density functional calculations
Categories
Funding
- EPSRC [EP/R013748/1, EP/H011455/1] Funding Source: UKRI
Ask authors/readers for more resources
A Density functional theory (DFT) approach has been used to shed light on the mechanism of a recently discovered rearrangement reaction for the conversion of spirocyclic indolenines into cyclopentanone-fused quinolines. A new base-mediated variant of this unusual rearrangement reaction has also been developed, that operates at much lower temperatures than those required in the analogous acidic reactions. The DFT study suggests that both the acid and base-mediated variants proceed via an enol/enolate intermediate, and the ease with which this key intermediate forms appears to be crucial in explaining the kinetic outcomes.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available