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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| http://dx.doi.org/10.1021/ol201985p | DOI Listing |
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Base-catalyzed Povarov reaction: an unusual [1,3] sigmatropic rearrangement to dihydropyrimidobenzimidazoles.
Org Lett
October 2011
Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan.
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.
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