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

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 journal › Article › peer-review

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 language	English
Pages (from-to)	11230-11243
Number of pages	14
Journal	Tetrahedron
Volume	61
Publication status	Published - 21 Nov 2005

Keywords

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

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

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.",

keywords = "pigments, heterocycles, pyrrolopyrroles, cyclisation, enamines, microwaves, FLUORESCENT DYES, REARRANGEMENT, DERIVATIVES, AMIDATION, NITRILES, HALIDES",

author = "Riggs, {R L} and Morton, {C J H} and Slawin, {A M Z} and Smith, {D M} and Westwood, {N J} and Austen, {W S D} and Stuart, {K E}",

year = "2005",

month = nov,

day = "21",

language = "English",

volume = "61",

pages = "11230--11243",

journal = "Tetrahedron",

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}

TY - JOUR

T1 - Synthetic studies related to diketopyrrolopyrrole (DPP) pigments. Part 3: Syntheses of tri- and tetra-aryl DPPs

AU - Riggs, R L

AU - Morton, C J H

AU - Slawin, A M Z

AU - Smith, D M

AU - Westwood, N J

AU - Austen, W S D

AU - Stuart, K E

PY - 2005/11/21

Y1 - 2005/11/21

N2 - 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.

AB - 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.

KW - pigments

KW - heterocycles

KW - pyrrolopyrroles

KW - cyclisation

KW - enamines

KW - microwaves

KW - FLUORESCENT DYES

KW - REARRANGEMENT

KW - DERIVATIVES

KW - AMIDATION

KW - NITRILES

KW - HALIDES

UR - http://www.scopus.com/inward/record.url?scp=27144469886&partnerID=8YFLogxK

M3 - Article

SN - 0040-4020

VL - 61

SP - 11230

EP - 11243

JO - Tetrahedron

JF - Tetrahedron

ER -

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

Abstract

Keywords

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