Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 3: Syntheses of tri- and tetra-aryl DPPs

R L Riggs, C J H Morton, A M Z Slawin, D M Smith, N J Westwood, W S D Austen, K E Stuart

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Novel synthetic methodologies leading towards 2,3,5-triaryl- and 2,3,5,6-tetraaryl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-diones (tri- and tetra-aryl-DPPs) and their derivatives have been investigated. Direct arylation of 3,6-diphenyl-DPP was possible using 1-fluoro-2,4dinitrobenzene. Acylation of ethyl 2-aryl-4,5-dihydro-5-oxopyrrole-3-carboxylates with N-arylbenzimidoyl chlorides in the presence of a strong base gives the novel 2,3,6-triaryl-DPPs together with the corresponding uncyclised enamines. A new and simple method for the synthesis of ethyl 1,2-diaryl-4,5-dihydro-5-oxopyrrole-3-carboxylates has led to an alternative route to triaryl-DPPs via reaction with benzonitrile under basic conditions, and combination of this with the benzimidoyl chloride methodology has enabled the synthesis of variously substituted 2,3,5,6-tetraphenyl-DPPs. (c) 2005 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)11230-11243
Number of pages14
JournalTetrahedron
Volume61
Publication statusPublished - 21 Nov 2005

Keywords

  • pigments
  • heterocycles
  • pyrrolopyrroles
  • cyclisation
  • enamines
  • microwaves
  • FLUORESCENT DYES
  • REARRANGEMENT
  • DERIVATIVES
  • AMIDATION
  • NITRILES
  • HALIDES

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