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Synthesis 1991; 1991(1): 86-90
DOI: 10.1055/s-1991-26388
DOI: 10.1055/s-1991-26388
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Electrophilic Cyclization and Thermal Rearrangement of Allylic 1,1-Dimethylisoureas
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Publikationsverlauf
Publikationsdatum:
17. September 2002 (online)
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A series of substituted 2-allyl-1,1-dimethylisoureas (allyl N,N-dimethylcarbamimidates) was prepared by the reaction of the corresponding allylic alcohols with dimethylcyanamide in the presence of sodium hydride. Treatment of the isoureas with mercuric acetate in acetonitrile, followed by reduction with sodium borohydride, afforded substituted 4,5-dihydrooxazoles. Thermal rearrangement of the 1,1-dimethylisoureas occurred in refluxing xylene to give trisubstituted ureas.