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Base-catalyzed Povarov reaction: an unusual [1,3] sigmatropic rearrangement to dihydropyrimidobenzimidazoles.

Authors
  • Chen, Chih-Hau
  • Yellol, Gorakh S
  • Lin, Po-Tsung
  • Sun, Chung-Ming
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Oct 07, 2011
Volume
13
Issue
19
Pages
5120–5123
Identifiers
DOI: 10.1021/ol201985p
PMID: 21888372
Source
Medline
License
Unknown

Abstract

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.

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