New oxidative transformations of phenolic and indolic oxazolines: an avenue to useful azaspirocyclic building blocks.
The oxidative cyclization of a phenolic amide to a spirolactam has long been regarded as an "impossible" reaction, because exposure of the substrates to a variety of oxidants results in formation of spirolactones with consequent loss of the amine segment. We recently communicated that this heretofore unknown transformation may be achieved by oxidation of oxazoline analogues of phenolic and indolic amides. Herein, we provide full details of our work.
Braun
N A
NA
Department of Chemistry, MS 60, Rice University, Houston, TX 77005-1892, USA.
Ousmer
M
M
Bray
J D
JD
Bouchu
D
D
Peters
K
K
Peters
E M
EM
Ciufolini
M A
MA
D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*
D001391:Azo Compounds; D007211:Indoles; D010080:Oxazoles; D010636:Phenols