Synthesis of substituted N-hydroxyureas via the in situ generation of t-butoxy isocyanate

Treatment of primary and secondary amines with tert-butylmesitylenesulfonoxycarbamate and a base afforded tert-butoxyurea, which when treated with an acid ultimately yielded substituted N-hydroxyureas. It is proposed that this proceeded via the generation of t-butoxy isocyanate in situ. This method...

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Bibliographic Details
Published in:Tetrahedron letters 2010-07, Vol.51 (27), p.3568-3570
Main Authors: Krause, Josef G., Leskiw, Brian D., Emery, Michelle L., McGahan, Megan E., McCourt, Mary P., Priefer, Ronny
Format: Article
Language:English
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Summary:Treatment of primary and secondary amines with tert-butylmesitylenesulfonoxycarbamate and a base afforded tert-butoxyurea, which when treated with an acid ultimately yielded substituted N-hydroxyureas. It is proposed that this proceeded via the generation of t-butoxy isocyanate in situ. This method allows for the synthesis of both mono and disubstituted N-hydroxyureas.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.05.002