King, FD and Aliev, AE and Caddick, S and Tocher, DA and 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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