Parallel synthesis and spectroscopic analysis of a collection of heterocycles based on the diazabenz[e]aceanthrylene core structure

Alan M. Jones, Tomas Lebl, Stephen Patterson, Tanja van Mourik, Herbert A. Früchtl, Douglas Philp, Alexandra M.Z. Slawin, Nicholas J. Westwood*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

A practical strategy for the synthesis of diazabenz[e]aceanthrylene-based heterocycles is reported. The key step in this approach is a microwave-assisted condensation and cyclisation reaction between an anthranilic acid derivative and a 2′-carbomethoxy substituted N-aryl lactam. The scope of the reaction has been explored as a function of both the nature and position of substituents in both components and variations in lactam ring size. Interesting structural and spectroscopic variations observed across the compound collection are described and explored using NMR, X-ray crystallography and computational techniques.

Original languageEnglish (US)
Pages (from-to)563-578
Number of pages16
JournalTetrahedron
Volume65
Issue number2
DOIs
StatePublished - Jan 10 2009

Keywords

  • Computational analysis
  • Heterocycles
  • Microwave
  • Variable temperature NMR analysis
  • Zipper reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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