Singlet oxygen oxidation of pyrroles: Synthesis and chemical transformations of novel 4,4-bis(trifluoromethyl)imidazoline analogs

Singlet oxygen oxidation of pyrroles: Synthesis and chemical transformations of novel 4,4-bis(trifluoromethyl)imidazoline analogs

Singlet oxygen or mCPBA oxidation of pyrrole 5b afforded a new series of 4,4-bis(trifluoromethyl)imidazolines with a para-substituted phenacyl side chain which are potent ACAT and cholesterol biosynthesis inhibitors. A novel singlet oxygen ring cleavage of pyrrole 5a and subsequent acid-catalyzed fa...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron Vol. 52; no. 34; pp. 11153 - 11162
Main Authors: Li, Hui-Yin, Drummond, Spencer, DeLucca, Indawati, Boswell, George A.
Format: Journal Article
Language:English
Published: Elsevier Ltd 19-08-1996
Subjects:
Dehydrocyclization
Imidazoline
Oxidation
Pyrrole
Singlet oxygen
Dehydrocyclization
Oxidation
Singlet oxygen
Imidazoline
Pyrrole
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Singlet oxygen or mCPBA oxidation of pyrrole 5b afforded a new series of 4,4-bis(trifluoromethyl)imidazolines with a para-substituted phenacyl side chain which are potent ACAT and cholesterol biosynthesis inhibitors. A novel singlet oxygen ring cleavage of pyrrole 5a and subsequent acid-catalyzed facile dehydrocyclization afforded a new series of 4,4-bis(trifluoromethyl)imidazolines with a p-fluorophenacyl side chain at the 5-position, which have shown potent acyl CoA: cholesterol acyltransferase (ACAT) and cholesterol biosynthesis inhibitory activities.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00578-9