Anti-tumour heterocycles. Part xiv. A new route to pyrrolo-[3,2-f]indoles and the novel pyrrolo[3,2-f; 4,5-f′]diindole system

Chunchatprasert, Laddawan; Shannon, P. V. R.

doi:10.1039/p19960001787

Cited by 21 publications

(9 citation statements)

References 7 publications

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“…Unfortunately treatment of 13 with TFA and TFAA, under the conditions that had been successful for the synthesis of 2, gave only the pyrrolo-[3,2-f]indole 18 where presumably mono-trifluoracylation had been followed by acid-catalyzed intramolecular condensation (Scheme 4). [32][33][34] Since 18 exhibits indolic, rather than pyrrolic, reactivity traits, and because 18 does not feature the required prochiral signature, we sought an alternative route for the synthesis of 12.…”

Section: Figure 4 Retrosynthetic Analysis Of Bis(dipyrrin) 10mentioning

confidence: 99%

Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton — Electron-poor pyrroles exhibit dramatically reduced nucleophilicity

Beshara¹,

Pearce²,

Thompson³

2008

Can. J. Chem.

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With the aim of furthering our investigations into the asymmetric complexation of dipyrrinato ligands, a dipyrrin bearing a stereogenic centre directly adjacent to the conjugated skeleton was synthesized. The electron-withdrawing nature of the chiral 4-(2,2,2-trifluoro-1-hydroxyethyl)- substituent significantly reduced the nucleophilicity of corresponding pyrroles, such that 2,2′-symmetrically substituted bis(dipyrrin)s bearing this motif were inaccessible. Furthermore, solutions of mononuclear dipyrrinato complexes were found to be less stable to acid-catalyzed decomplexation than the corresponding dinuclear complexes.Key words: dipyrrin, dipyrromethene, complexation, electron-poor pyrrole, chirality.

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Section: Figure 4 Retrosynthetic Analysis Of Bis(dipyrrin) 10mentioning

confidence: 99%

Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton — Electron-poor pyrroles exhibit dramatically reduced nucleophilicity

Beshara¹,

Pearce²,

Thompson³

2008

Can. J. Chem.

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“…Dielectrophiles can react twice with pyrroles in a one-pot reaction in a similar fashion. Chunchatprasert and Shannon disclosed the double substitution of 2,3-unsubstituted pyrrolocyclohexanones 72 with pyrrole 76 ( Scheme 14 ) [ 58 ]. N-H pyrrolocyclohexanone 72 was unreactive under the given conditions.…”

Section: Synthesis Of [23]-fused Polyheterocyclic Structuresmentioning

confidence: 99%

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

Horsten¹,

Dehaen²

2021

Molecules

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This review focuses on the synthesis of polyheterocyclic structures with a variety of medicinal and optoelectronic applications, starting from readily available 4,5,6,7-tetrahydroindol-4-one analogs. First, routes toward the 4,5,6,7-tetrahydroindol-4-one starting materials are summarized, followed by synthetic pathways towards polyheterocyclic structures which are categorized based on the size and attachment point of the newly formed (hetero)cyclic ring.

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“…Chunchatprasert et al have prepared pyrrolo[2,3- f ]indole 151 (24%) by condensing biselectrophilic 5-acetoxy-4-acetylpyrrole 149 with 2,3-unsubstituted pyrrole 150 under the influence of montmorillonite clay in 1,2-dichloroethane solvent (Scheme 39) [87].…”

Section: Smaller Organic Donor Systemsmentioning

confidence: 99%

Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

Vlasselaer

Dehaen

2016

Molecules

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Abstract:The objective of this review is to give an overview of the synthetic methods to prepare different indolo [3,2-b]carbazoles and similar systems with a potential use in electro-optical devices such as OLEDs (organic light emitting diode), OPVs (organic photovoltaic) and OFETs (organic field effect transistor). Some further modifications to the core units and their implications for specific applications are also discussed.

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Anti-tumour heterocycles. Part xiv. A new route to pyrrolo-[3,2-f]indoles and the novel pyrrolo[3,2-f; 4,5-f′]diindole system

Abstract: Anti-tumour heterocycles. Part XIV.' A new route to pyrrolo-[ 3,2-fJ indoles and the novel pyrrolo [ 3,2& 4,5-f'] diindole system

Cited by 21 publications

References 7 publications

Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton — Electron-poor pyrroles exhibit dramatically reduced nucleophilicity

Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton — Electron-poor pyrroles exhibit dramatically reduced nucleophilicity

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

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