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A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation

King, FD; Aliev, AE; Caddick, S; Tocher, DA; Courtier-Murias, D; (2009) A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation. ORG BIOMOL CHEM , 7 (1) 167 - 177. 10.1039/b815195d.

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Abstract

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.

Type:Article
Title:A facile synthesis of pyrrolo-(di)-benzazocinones via an intramolecular N-acyliminium ion cyclisation
DOI:10.1039/b815195d
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 > Chemistry

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