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Cyclization Reaction of Donor-Acceptor Oxiranes with N,N'-Disubstituted Thioureas: A Domino Process to trans-Dihydropyrimidines.

Organic Letters 2018 October 9
An unprecedented cyclization reaction of donor-acceptor oxiranes with N,N'-disubstituted thioureas to construct trans-dihydropyrimidines is presented. Preliminary reaction mechanism studies demonstrated that the reaction underwent sequential cycloaddition/amine ester exchange/oxygen-sulfur exchange/desulfuration/Michael addition process. A wide range of trans-dihydropyrimidines were produced with high yields up to 94% by using this method.

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