Copy the page URI to the clipboard
Lory, Pedro M.J.; Jones, Raymond C.F.; Iley, James N.; Coles, Simon J. and Hursthouse, Michael B.
(2006).
DOI: https://doi.org/10.1039/b605458g
Abstract
N-Alkylation of 4,5-dihydroimidazoles with alkene-containing bromomethyl ketones and treatment of
the so-formed 4,5-dihydroimidazolium ions with DBU gives rise to an intramolecular 1,3-dipolar
cycloaddition reaction that affords (via a reaction cascade involving eliminative ring-opening,
recyclisation and prototropic tautomerism) unexpected hexahydropyrrolo[1,2,3-de]quinoxaline
products. Steric bulk in both the dihydroimidazole and the dipolarophile allows isolation of an
imidazo[1,2-a]indole, the initial product of cycloaddition. When the bromomethyl ketone contains no
other functionality, or when cycloaddition is inhibited due to steric constraints, the dihydroimidazolium
ion undergoes ring-opening hydrolysis followed by recyclization of the exposed amino ketone to afford
either 3-alkyl-1-formylpiperazine-2-ones or 3-aryl-1-formyl-1,4,5,6-tetrahydropyrazines.
Viewing alternatives
Metrics
Public Attention
Altmetrics from AltmetricNumber of Citations
Citations from DimensionsItem Actions
Export
About
- Item ORO ID
- 5954
- Item Type
- Journal Item
- ISSN
- 1477-0520
- Extra Information
- Some of the symbols may not have transferred correctly into this bibliographic record and/or abstract.
- Keywords
- intramolecular; 1,3-dipolar cycloaddition; dihydroimidazolium ylides; imidazoline ylides;
- Academic Unit or School
-
Other Departments > Other Departments
Other Departments - Depositing User
- James Iley