Medium-Ring Nitrogen Heterocycles through Migratory Ring Expansion of Metalated Ureas

Jessica Hall, Johnathan Matlock, John Ward, Katharine V. Gray, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalSpecial issue (Academic Journal)peer-review

65 Citations (Scopus)
305 Downloads (Pure)

Abstract

Simple benzo-fused nitrogen heterocycles (indolines, tetrahydroquinolines, and their homologues) undergo migratory ring expansion through deprotonation of their benzylic urea derivatives with lithium diisopropylamide (LDA) in the presence of N,N′-dimethylpropylideneurea (DMPU). The products of the reactions are benzodiazepines, benzodiazocines, and their homologues, with ring sizes of 8–12. The reactions tolerate a range of substituent patterns and types, and may exhibit enantiospecificity or diastereoselectivity. Considerable complexity is rapidly generated in an efficient synthesis of these otherwise difficult-to-obtain medium-ring nitrogen heterocycles.
Original languageEnglish
Pages (from-to)11153-11157
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number37
Early online date21 Jul 2016
DOIs
Publication statusPublished - 5 Sep 2016

Structured keywords

  • BCS and TECS CDTs

Keywords

  • Heterocycles
  • Indolines
  • Organolithium
  • Ring expansion
  • Tetrahydroquinolines

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