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

doi:10.1016/j.tet.2004.10.027

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	727-738
Number of pages	12
Journal	Tetrahedron
Volume	61
DOIs	https://doi.org/10.1016/j.tet.2004.10.027
Publication status	Published - 17 Jan 2005

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title = "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",

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.",

author = "Morton, \{C J H\} and Riggs, \{R L\} and Smith, \{D M\} and Westwood, \{N J\} and P Lightfoot and Slawin, \{A M Z\}",

year = "2005",

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AU - Morton, C J H

AU - Riggs, R L

AU - Smith, D M

AU - Westwood, N J

AU - Lightfoot, P

AU - Slawin, A M Z

PY - 2005/1/17

Y1 - 2005/1/17

N2 - 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.

AB - 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.

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DO - 10.1016/j.tet.2004.10.027

M3 - Article

SN - 0040-4020

VL - 61

SP - 727

EP - 738

JO - Tetrahedron

JF - Tetrahedron

ER -

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

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