Base-Catalyzed Povarov Reaction: An Unusual [1,3] Sigmatropic Rearrangement to Dihydropyrimidobenzimidazoles

A novel base-catalyzed Povarov reaction of arylamines, aldehydes, and electron-deficient dienophiles has been developed. An unprecedented in situ [1,3] sigmatropic rearrangement leading to 4,10-dihydropyrimido[1,2-a]benzimidazoles has also been discovered. An insight of the plausible mechanism is di...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (19), p.5120-5123
Main Authors: Chen, Chih-Hau, Yellol, Gorakh S, Lin, Po-Tsung, Sun, Chung-Ming
Format: Article
Language:English
Subjects:
Benzimidazoles - chemistry
Catalysis
Crystallography, X-Ray
Hydrogen - chemistry
Models, Molecular
Molecular Structure
Pyridines - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel base-catalyzed Povarov reaction of arylamines, aldehydes, and electron-deficient dienophiles has been developed. An unprecedented in situ [1,3] sigmatropic rearrangement leading to 4,10-dihydropyrimido[1,2-a]benzimidazoles has also been discovered. An insight of the plausible mechanism is discussed and supported by X-ray crystal study. This cascade reaction is achieved in a one-pot multicomponent fashion on soluble support under microwave conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201985p