A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation.
ORG BIOMOL CHEM
167 - 177.
A facile, moderate to high yielding synthesis of hexahydro-(di)-benzazocinones is described via an intramolecular N-acyliminium ion cyclisation. The iminium ion intermediates are formed from the readily available 4,4-diethoxybutyl amides with an excess of triflic acid. For electron-withdrawing substituents, better yields were obtained from the pre-formed 2-hydroxypyrrolidine amides. From NMR studies, at ambient temperatures the pyrrolo-benzazocin-3-ones exist as a slowly equilibrating mixture of two conformations.
|Title:||A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation|
|Keywords:||DOPAMINE D-3 RECEPTOR, CONFORMATIONAL-ANALYSIS, BIOLOGICAL EVALUATION, FUSED HETEROCYCLES, DERIVATIVES, DESIGN, 1,2,3,4-TETRAHYDROISOQUINOLINES, SELECTIVITY, ANALOGS, RINGS|
|UCL classification:||UCL > School of BEAMS > Faculty of Maths and Physical Sciences
UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
Archive Staff Only