Journal
TETRAHEDRON
Volume 65, Issue 26, Pages 5102-5109Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.04.071
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Funding
- NIGMS NIH HHS [R01 GM079644, R01 GM079644-02] Funding Source: Medline
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Vinyl benzoxazinones undergo decarboxylation in the presence of palladium catalysts to form palladium-polarized aza-ortho-xylylenes, which are versatile reaction intermediates. These palladium-polarized aza-ortho-xylylenes are generated under exceptionally mild conditions and undergo a plethora of different reactions depending on the reaction conditions. Specifically, they undergo dimerization reactions to produce macrocycles, cyclizations to form dihydroquinolines, cycloadditions with electrophilic p-bonds, and nucleophilic attack by amines. Thus, a wide array of structurally unique aniline derivatives can be accessed from these unique intermediates. (C) 2009 Elsevier Ltd. All rights reserved.
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