Consecutive Ring Expansion and Contraction for the Synthesis of 1-Aryl Tetrahydroisoquinolines and Tetrahydrobenzazepines from Readily Available Heterocyclic Precursors

Jessica E. Hill, Johnathan V. Matlock, Quentin Lefebvre, Katie G. Cooper, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

12 Citations (Scopus)
155 Downloads (Pure)

Abstract

Tetrahydroisoquinolines and tetrahydrobenzazepines were prepared by acid-promoted ring contraction of cyclic ureas, which were themselves formed by ring expansion of indolines and tetrahydroquinolines. The consequent overall one-carbon insertion reaction gives these 6- and 7-membered heterocyclic scaffolds in three steps from readily available precursors. Other ring sizes may be formed by an alternative elimination reaction of bicyclic structures. Scalability of the method was demonstrated by operating it in a flow system.
Original languageEnglish
Pages (from-to)5788-5791
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number20
Early online date14 Mar 2018
DOIs
Publication statusPublished - 14 May 2018

Structured keywords

  • BCS and TECS CDTs

Keywords

  • benzazepines
  • heterocycle
  • ring contraction
  • tetrahydroisoquinolines
  • urea

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