Solid-supported nitroso hetero-Diels-Alder reactions. 3. Acid-mediated transformation of cycloadducts by scission of the oxazine C-O bonds.
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.
Krchnák
Viktor
V
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556, USA. vkrchnak@nd.edu
Moellmann
Ute
U
Dahse
Hans-Martin
HM
Miller
Marvin J
MJ
D002244:Carbon / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry*
D006571:Heterocyclic Compounds; D009603:Nitroso Compounds; D010078:Oxazines; D011108:Polymers; D002244:Carbon; D014269:Trifluoroacetic Acid; D010100:Oxygen