19167-98-7

Usage

Uses

Used in Laboratory Research:
2-pyrrol-1-ylacetic acid is used as a research compound for the development of new molecules or substances in laboratories. It is particularly valuable in academic and research studies regarding pyrrole chemistry, where it can serve as a building block or a starting material for the synthesis of more complex molecules.
Used in Academic and Research Studies:
2-pyrrol-1-ylacetic acid is used as a reference compound in academic and research studies focused on pyrrole chemistry. It helps researchers understand the properties and behavior of pyrrole-based compounds, which can be crucial for the development of new chemical processes and applications.

InChI:InChI=1/C6H7NO2/c8-6(9)5-7-3-1-2-4-7/h1-4H,5H2,(H,8,9)

Upstream product

• 5145-67-5 1-ethoxycarbonylmethyl-1H-pyrrole 
• 50966-72-8 pyrrole-1-yl-acetic acid methyl ester 
• 86428-38-8 1,4-dichloro-1,4-dimethoxybutane 
• 56-40-6 glycine 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 108-31-6 maleic anhydride 
• 459-73-4 GlyOEt*HCl 

Downstream Products

• 89059-09-6 1H-pyrrolizine-2(3H)-one 
• 6719-02-4 2-(1H-pyrrol-1-yl)ethanol 

Relevant academic research and scientific papers

Isothiourea-Catalyzed Enantioselective Functionalization of 2-Pyrrolyl Acetic Acid: Two-Step Synthesis of Stereodefined Dihydroindolizinones

Catalytic enantioselective functionalization of 2-pyrrolyl acetic acid with trichloromethyl enones using isothiourea catalysis is reported, leading to a range of stereodefined diesters and diamides after nucleophilic ring opening with either methanol or b

Direct imine acylation for molecular diversity in heterocyclic synthesis

Imines and carboxylic acids have been directly coupled using propylphosphonic acid anhydride and NEt(i-Pr)2 to give N-acyliminium ions, which were intramolecularly trapped with oxygen, nitrogen, sulfur, and carbon nucleophiles to provide a wide range of structurally diverse heterocycles.

Friedel-Crafts alkylation of natural amino acid-derived pyrroles with CF3-substituted cyclic imines

Natural amino acid-derived ethyl 2-(1-pyrrolyl)alkanoates react with 2-trifluoromethyl-1-azacycloalkenes selectivity at the β-position of the pyrrole moiety to afford ethyl 2-[3-(1-trifluoromethyl-2-azacycloalkyl)pyrrol-1- yl]alkanoates.

Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores

Enantiopure alkaloid mimics are synthesized via high yielding intramolecular cycloadditions of photogenerated azaxylylenes tethered to pyrroles, with further growth of molecular complexity via post-photochemical transformations of primary photoproducts. This expeditious access to structurally unprecedented polyheterocyclic cores is being developed in the context of diversity-oriented synthesis, as the modular design allows for rapid "pre-assembly" of diverse photoprecursors from simple building blocks/diversity inputs.

2-(1H-pyrrolyl)carboxylic acids as pigment precursors in garlic greening

Six model compounds having a 2-(1H-pyrrolyl)carboxylic acid moiety and a hydrophobic R group were synthesized to study their effects on garlic greening, the structures of which are similar to that of 2-(3,4-dimethyl-1H-pyrrolyl)-3- methylbutanoic acid (PP

CYCLIC HYDROCARBONS WITH AN AMINOALKYL SIDECHAIN

Provided are cyclic hydrocarbons of Formula I with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.

Peptide Synthesis Using the Pyrrole Ring as an Amino Protecting Group

The utility of a pyrrole ring as an amino protecting group for amino acids in peptide synthesis has been studied.The N-termini of various amino acids (1) were protected with a pyrrole ring by treatment with 2,5-dimethoxytetrahydrofuran (10) to give 2-substituted 2-(1-pyrrolyl)acetic acids (11).The peptide bond between (11) and amino acid methyl ester (2) was formed using N,N'-dicyclohexylcarbodiimide, and the pyrrole ring was cleaved by ozonolysis and hydrolysis without the cleavage of a peptide bond to give the corresponding dipeptide compounds (26) in good yields.

Reactivity of a tetrahedral Intermediate in Hydrolysis of N-Acetylpyrrole

Base hydrolysis of N-acetylpyrrole (1a) involves formation of an anionic tetrahedral intermediate (2a).The equilibrium constant between these two species can be estimated by extrapolation based on the equilibrium constants for hydration of N-trichloroacetyl and N-trifluoroacetylpyrrole and the estimated pKa for deprotonation of the hydrates of these compounds.Inductive effects upon hydration and deprotonation of the hydrates were estimated by analogy with inductive effects upon the equilibrium reactions of chloral and acetaldehyde.The free energies of activation for formation and return of 2a are approximately 16 and 12.5 Kcal mole-1 respectively and for conversion of 2a to products 11 Kcal mole-1 in aqueous 1M OH-.

269. Intramolecular Carbenoid Reaction of Pyrrole Derivatives. Efficient Syntheses of Pyrrolizinone and Dihydroindolizinone

The copper-catalyzed pyrolysis of 1-diazo-3-(pyrrol-1-yl)-2-propanone (1a) and 1-diazo-4-(pyrrol-1-yl)-2-butanone (1b) in benzene solution gave 1H-pyrrolizin-2-(3H)-one (4a) and 5,6-dihydroindolizin-7(8H)-one (4b), respectively, in quantative yield.Similar pyrolysis of 1-diazo-4-(3-methylindol-1-yl)-2-butanone (9) was less efficient giving 1-methylbenzo-5,6-dihydroindolizin-7(8H)-one (10) and 4-(3-methylindol-1-yl)-but-1-en-3-one (11) in 7percent and 24percent yield, respectively.

1,4-Dichloro-1,4-dimethoxybutane as a Mild Reagent for the Conversion of Primary Amines to Pyrroles. Synthesis of a Pyrrole Compound from Tobacco

1,4-dichloro-1,4-dimethoxybutane (2) reacts with primary amines, amino esters, and amino acids to give the corresponding N-substituted pyrroles.The synthesis of compound 9, a compound found in flue-cured tobacco, is described.