The Synthesis of 3-Substituted Pyrroles from Pyrrole

Anderson, Hugh J.; Loader, C. E.

doi:10.1055/s-1985-31211

Cited by 82 publications

(36 citation statements)

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“…Metallation of pyrroles at C3 has enabled convenient preparation of derivatives that were prepared previously by cumbersome means [417]. Selective C3 metallation is achieved conveniently by halogen-metal exchange on 3-bromo-1-(triisopropylsilyl) pyrrole (163) by virtue of the steric bulk of the TIPS group (Scheme 4.79) [245].…”

Section: C-metallated Pyrrolesmentioning

confidence: 99%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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Section: C-metallated Pyrrolesmentioning

confidence: 99%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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“…For this purpose, tBu, [35] triphenylmethyl and triisopropylsilyl (TIPS) groups have been used as bulky substituents. [14] Among them, the TIPS group is likely to be the most practical in terms of b-selectivity [36] as well as easy removability. [37] In fact, there have been some reports on direct b-alkylation of N-TIPS-pyrrole (17) [38] via the S E Ar process (Scheme 14).…”

Section: Use Of Pyrroles With a Bulky Group On The Nitrogen Atommentioning

confidence: 99%

“…Under such situation, how do you alkylate pyrroles at the b-position regioselectively? In order to offer clear and valuable guidance to the query, this Concept article will focus on providing an overview with respect to "selective synthesis of b-alkylpyrroles from pyrroles" mainly through the S E Ar route, [14] wherein our recent achievements will be also presented.…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of β‐Alkylpyrroles

Tsuchimoto

2011

Chemistry A European J

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β-Alkylpyrroles are key structural motifs found in many natural products and biologically active compounds as well as functional organic materials. For this reason, synthetic chemists continue to be interested in construction of the framework of β-alkylpyrroles. Due to sufficient aromaticity and π-excessive nature of pyrroles, a straightforward approach to β-alkylpyrroles should be electrophilic aromatic substitution (S(E)Ar) toward the pyrrole ring. However, since a primary nucleophilic site of pyrroles is an α-position, some "trick" is required to direct incoming alkyl electrophiles toward a β-position. This Concept article focuses on presenting previous efforts that have been devoted to the synthesis of β-alkylpyrroles, mainly through the S(E)Ar route.

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“…Furthermore, this protecting group is easily removed under simple basic hydrolysis. 23 We now report a facile six-step pathway to synthesise ω-(pyrrol-3-yl)alkylphosphonic acids with every step being carried out under mild conditions with good yields. The reaction conditions can be easily modified to accommodate various pyrrole derivatives.…”

Section: Synthetic Pathways To Substituted Pyrrole Derivativesmentioning

confidence: 99%

Synthesis of a Number of 3‐Alkyl Substituted Pyrrole Monomers

2009

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The problem of delamination of electro-deposited polypyrrole (PPY) layers on several substrates can be avoided by using an adhesion promoting system. A new class of compounds-ω-(pyrrol-3-yl)alkylphosphonic acids have been designed to link polypyrrole layers covalently to metal oxide surfaces. Synthetic routes, which lead to the formation of 3-substituted pyrroles with surface active groups are described. The synthesis and characterization are shown in detail. 1-Phenylsulfonyl pyrrole was utilized as a precursor in the synthesis of 3-substituted pyrroles via Friedel-Crafts acylation reaction. Subsequently, two methods were used to synthesize ω-(pyrrol-3-yl)alkylphosphonic acid esters. One starts from the brominated oxoalkyl derivatives by removing the protecting group followed by reduction yielding ω-(pyrrol-3-yl)alkylphosphonic acid esters. This method is suitable for hexyl or longer chain derivatives. The other is the reduction of carbonyl group followed by de-protection, which is successful for short as well as long chain derivatives. Finally, ω-(pyrrol-3-yl)alkylphosphonic acids were obtained by hydrolysis of the ester derivatives.

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The Synthesis of 3-Substituted Pyrroles from Pyrrole

Cited by 82 publications

References 0 publications

Five‐Membered Heterocycles: Pyrrole and Related Systems

Five‐Membered Heterocycles: Pyrrole and Related Systems

Selective Synthesis of β‐Alkylpyrroles

Synthesis of a Number of 3‐Alkyl Substituted Pyrrole Monomers

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