A novel Barton decarboxylation produces a 1,4-phenyl radical rearrangement domino reaction
Tetrahedron(2018)
Abstract
A novel 1,4-Phenyl radical rearrangement (1,4-PhRR) is described in a typical Barton decarboxylation procedure. While carrying out this reaction in presence of a N,N-disubstituted β-amino acid derivative, the decarboxyphenyl rearranged derivative is obtained, as well as in presence of β-N,N-acylamide. On the other hand, secondary amines give the β-lactam derivative without rearrangement, as well as N-Fmoc derivatives give the normal decarboxylation reaction. In regards of amines which are far away from the carboxylic group, such as δ-amino acid derivatives, the reaction occur through a typical Barton decarboxylation without rearrangement. The diversity of the reaction proves synthetic usefulness paving the way to interesting biologically active compounds.
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Key words
Barton decarboxylation,Radical rearrangement,Domino reaction,Phenethylamine,Amphetamine,Ethamphetamine,Adrenaline,Ephedrine
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