Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 2: The use of esters in place of nitriles in standard DPP syntheses: Claisen-type acylations and furopyrrole intermediates

C J H Morton, R L Riggs, D M Smith, N J Westwood, P Lightfoot, A M Z Slawin

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22 Citations (Scopus)

Abstract

Ethyl 2-aryl-4,5-dihydro-5-oxopyrrole-3-carboxylates react with esters or acyl halides in the presence of a strong base to give 4-acyl derivatives, which exist predominantly as either E- or Z-enols. These are cyclised, either in solution at temperatures > 200degreesC or by microwave irradiation, to 3,6-di substituted 1H-furo[3,4-c]pyrrolediones which, after N-protection, are convertible by reaction with primary amines into novel NN'-disubstituted DPP derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)727-738
Number of pages12
JournalTetrahedron
Volume61
DOIs
Publication statusPublished - 17 Jan 2005

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