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  • Title: Solid-supported nitroso hetero-Diels-Alder reactions. 3. Acid-mediated transformation of cycloadducts by scission of the oxazine C-O bonds.
    Author: Krchnák V, Moellmann U, Dahse HM, Miller MJ.
    Journal: J Comb Chem; 2008; 10(1):112-7. PubMed ID: 18067270.
    Abstract:
    Polymer-supported dihydro[1,2]oxazine derivatives were prepared by acyl- and arylnitroso hetero-Diels-Alder reactions and exposed to strong (trifluoroacetic) acid during cleavage from resin-bound linkers. Cycloadducts prepared from cyclic dienes containing electron-donating substituents at the C6 oxazine carbon promoted formation of carbocations by cleavage of the C-O bond. The carbocations were quenched by nucleophilic reagents including triethylsilane, water, and alcohols and provided access to novel derivatives of N-alkyl hydroxamates. Products were submitted to biological assays, and the results are reported.
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