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, Norbert A.,Ousmer, Malika,Bray, Jonathan D.,Bouchu, Denis,Peters, Karl,Peters, Eva-Maria,Ciufolini, Marco A.
p. 4397 - 4408
(2007/10/03)
Synthesis of spirolactams from tyrosine amides and related substances
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
Braun, Norbert A.,Ciufolini, Marco A.,Peters, Karl,Peters, Eva-Maria
p. 4667 - 4670
(2007/10/03)
Liquid Crystalline trans-4-(ω-Cyanalkyl)cyclohexylester and 4-(ω-Cyanalkyl)phenylesters
The synthesis of the title esters 1 and 2a-e (n = 0-3) and their mesomorphic properties are described.When the alkyl-spacer n between the polar CN-group and the cyclohexane ring of cyanalkyl-cyclohexylesters 1 is increased the difference of the clearing points between the phenylesters 2 and the cyclohexylesters 1 decreases to nearly zero.The reason of higher clearing temperatures of 2 is a dynamic conformational effect of ring inversion of cyclohexane in the ester 1 with two polar substituents at the ring.
Deutscher, H.-J.,Krieg, R.,Frach, R.,Kresse, H.,Zaschke, H.
p. 963 - 974
(2007/10/02)
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