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An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones

King, FD; Aliev, AE; Caddick, S; Copley, RCB; (2009) An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones. ORG BIOMOL CHEM , 7 (17) 3561 - 3571. 10.1039/b907400g.

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Abstract

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.

Type:Article
Title:An investigation into the electrophilic cyclisation of N-acyl-pyrrolidinium ions: a facile synthesis of pyrrolo-tetrahydroisoquinolones and pyrrolo-benzazepinones
DOI:10.1039/b907400g
Keywords:ELECTROORGANIC CHEMISTRY, DERIVATIVES, CARBON
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry
UCL > VP Enterprise

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