210707-18-9Relevant academic research and scientific papers
Synthesis of spirolactams from tyrosine amides and related substances
Braun, Norbert A.,Ciufolini, Marco A.,Peters, Karl,Peters, Eva-Maria
, p. 4667 - 4670 (1998)
Oxidation of oxazolines derived from phenolic ω-arylalkanoic acids such as tyrosine with iodobenzene diacetate leads to spirocyclic amides in moderate yields. This reaction was heretofore unknown due to the propensity of free amide analogs of the oxazolin
New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building-blocks
Braun, Norbert A.,Ousmer, Malika,Bray, Jonathan D.,Bouchu, Denis,Peters, Karl,Peters, Eva-Maria,Ciufolini, Marco A.
, p. 4397 - 4408 (2007/10/03)
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.
