930296-79-0Relevant academic research and scientific papers
An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: A facile synthesis of Pyrrolo-tetrahydroisoquinolones and Pyrrolo-benzazepinones
King, Frank D.,Aliev, Abil E.,Caddick, Stephen,Copley, Royston C. B.
experimental part, p. 3561 - 3571 (2010/01/06)
The triflic acid-mediated cyclisation of N-arylmethyl- and N-arylethyl-acylpyrrolidinium ions gave moderate to good yields of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones respectively. Electron-donating R substituents enhanced the rate of reaction and gave higher yields than electron-withdrawing substituents. Substituents on the methyl or ethyl chain in general enhanced the reaction, unless sterically encumbered. The equivalent acylpiperidinium ions cyclised much slower and in lower yield.
A facile three-step synthesis of (±)-crispine A via an acyliminium ion cyclisation
King, Frank D.
, p. 2053 - 2056 (2007/10/03)
A high yielding cyclisation of the readily available N-(4,4-diethoxybutyl)-2-(3,4-dimethoxyphenyl)acetamide to 8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-o ne is described. The latter can be reduced with either AlH3
