24059-71-0

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Methylphenyl)-2-pyrrolizinone is used as a building block for the synthesis of pharmaceutical compounds due to its potential biological activities and therapeutic properties. It serves as a precursor in the development of new drugs, contributing to the creation of innovative medications.
Used in Drug Synthesis:
In the field of drug synthesis, 1-(2-Methylphenyl)-2-pyrrolizinone is utilized as a key component for creating various pharmaceutical compounds. Its unique structure and properties make it a valuable asset in the design and production of novel medications with potential therapeutic benefits.

InChI:InChI=1/C11H13NO/c1-9-5-2-3-6-10(9)12-8-4-7-11(12)13/h2-3,5-6H,4,7-8H2,1H3

Upstream product

• 96-48-0 4-butanolide 
• 95-53-4 o-toluidine 
• 41790-76-5 N-(4-Chlorbutyryl)-o-toluidin 
• 616-45-5 2-pyrrolidinon 
• 615-37-2 ortho-methylphenyl iodide 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 110-63-4 Butane-1,4-diol 
• 15924-70-6 Cyclopropancarbonsaeure-o-toluidid 
• 4641-57-0 1-phenylpyrrolidin-2-one 
• 624-31-7 4-tolyl iodide 
• 1036030-62-2 [bis(1,10-phenanthroline)copper][bis(pyrrolidin-2-one)copper] 
• 6729-60-8 tris(2-methylphenyl)bismuth dichloride 

Downstream Products

• 186667-86-7 N-(2-methylphenyl)pyrrolidine-2-thione 
• 208646-52-0 N-(2-methylphenyl)-6-aminohexan-3-one 
• 13691-29-7 1-(4-amino-2-methyl-phenyl)-pyrrolidin-2-one 
• 208646-53-1 3-methoxy-2-oxo-4-propionyl-1-(2-methylphenyl)-1,2,5,6-tetrahydropyridine 
• 162142-33-8 3-hydroxy-2-oxo-4-propionyl-1-(2-methylphenyl)-1,2,5,6-tetrahydropyridine 
• 186667-91-4 diethyl [1-(2-methylphenyl)pyrrolidin-2-ylidene]malonate 
• 860361-32-6 1-(2-methyl-4-nitro-phenyl)-pyrrolidin-2-one 
• 41790-73-2 2-(2-oxopyrrolidin-1-yl)-benzoic acid 

Relevant academic research and scientific papers

Conformational Analysis of Rotational Barriers in N-Arylpyrrolidin-2-ones

The structures of N-phenylpyrrolidin-2-one and the three isomeric N-tolylpyrrolidin-2-ones have been studied by single-crystal X-ray diffraction, as a basis for the conformational analysis of the barrier to rotation around the single bond between the rings.Force-field simulation of the molecular structure is consistent with a rotational barrier of 7 kJ mol-1.Crystal data: N-phenylpyrrolidin-2-one, orthorhombic, Pbca, a = 14.114 (3), b = 6.879 (4), c = 17.386 (5) Angstroem, R = 0.059 for 1110 unique reflections o4?(Fo)>; N-(2-methylphenyl)pyrrolidin-2-one,orthorhombic, Pbca, a = 16.999 (4), b = 16.411 (2), c = 7.008 (2) Angstroem, R = 0.077 for 1479 unique reflections o4?(Fo)>; N-(3-methylphenyl)pyrrolidin-2-one, monoclinic, P21/c, a = 10.411 (2), b = 7.645 (2), c = 12.782 (1) Angstroem, β = 110.32 (1) deg, R = 0.065 for 1641 unique reflections o4?(Fo)>; N-(4-methylphenyl)pyrrolidin-2-one, orthorhombic, P212121, a = 7.668 (2), b = 10.804 (2), c = 11.456 (1) Angstroem, R = 0.054 for 1155 unique reflections o4?(Fo)>.

Ruthenium-catalyzed synthesis of: N -substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines

Herein, we report the first example of synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step, which was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene-phosphine-phosphine ligand as the catalyst.

Aluminium Chloride-Mediated Synthesis of 1-Chloro-2,2,2-Trifluoroethylidene-Substituted Pyrrolidones

An aluminium chloride-mediated cascade reaction between pyrrolidones and trifluoroacetic anhydride is reported. Functionally diverse 1-chloro-2,2,2-trifluoroethylidene-substituted pyrrolidones were obtained in moderate to high yields through electrophilic trifluoroacetylation, nucleophilic chlorination, and elimination. This procedure has a wide scope, good functional-group tolerance and the reaction conditions are amenable to scale up. Additionally the obtained 1-chloro-2,2,2-trifluoroethylidene products can be applied to further functionalization as trifluoromethyl-containing building blocks. Some of the title compounds showed fungicidal activity against cucumber downy mildew (CDM). (Figure presented.).

Novel tertiary sulfonamides as potent anti-cancer agents

For adult women in the United States, breast cancer is the most prevalent form of cancer. Compounds that target dysregulated signal transduction can be efficacious anti-cancer therapies. A prominent signaling pathway frequently dysregulated in breast canc

An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C?H Bond Activations

C?H activation is a versatile tool for appending aryl groups to aromatic systems. However, heavy demands on multiple catalytic cycle operations and site-selectivity have limited its use for graphene segment synthesis. A Pd-catal- yzed one-step synthesis of functionalized triphenylene frameworks is disclosed, which proceeds by 2- or 4-fold C?H arylation of unactivated benzene derivatives. A Pd2(dibenzylideneacetone)3 catalytic system, using cyclic diaryliodonium salts as π-extending agents, leads to site-selective inter- and intramolecular tandem arylation sequences. Moreover, N-substituted triphenylenes are applied to a field-effect transistor sensor for rapid, sensitive, and reversible alcohol vapor detection.

Green alternative solvents for the copper-catalysed arylation of phenols and amides

Investigation of the use of green organic solvents for the Cu-catalysed arylation of phenols and amides is reported. Alkyl acetates proved to be efficient solvents in the catalytic processes, and therefore excellent alternatives to the typical non-green solvents used for Cu-catalysed arylation reactions. Solvents such as isosorbide dimethyl ether (DMI) and diethyl carbonate also appear to be viable possibilities for the arylation of phenols. Finally, a novel copper catalysed acyl transfer process is reported.

Cyclization of N-arylcyclopropanecarboxamides into N-arylpyrrolidin-2-ones under electron ionization and in the condensed phase

Rationale: Mass spectrometry is known as an excellent method to predict the behavior of organic compounds in solution. The behavior of organic compounds in the gas phase inside the ion source of a mass spectrometer allows their intrinsic properties to be defined, avoiding the influence of intermolecular interactions, counter ions and solvent effects. Methods: Arylpyrrolidin-2-ones were obtained by condensed-phase synthesis from the corresponding N-arylcyclopropanecarboxamides. Electron ionization (EI) with accurate mass measurements by high-resolution time-of-flight mass-spectrometry and quantum chemical calculations were used to understand the behavior of the molecular radical cations of N-arylcyclopropanecarboxamides and N-arylpyrrolidin-2-ones in the ion source of a mass spectrometer. The geometries of the molecules, transition states, and intermediates were fully optimized using DFT-PBE calculations. Results: Fragmentation schemes, ion structures, and possible mechanisms of primary isomerisation were proposed for isomeric N-arylcyclopropanecarboxamides and N-arylpyrrolidin-2-ones. Based on the fragmentation pattern of the N-arylcyclopropanecarboxamides, isomerisation of the original M+? ions into the M+? ions of the N-arylpyrrolidin-2-ones was shown to be only a minor process. In contrast, this cyclization proceeds easily in the condensed phase in the presence of Br?nsted acids. Conclusions: Based on the experimental data and quantum chemical calculations the principal mechanism of decomposition of the molecular ions of N-arylcyclopropanecarboxamides involves their direct fragmentation without any rearrangements. An alternative mechanism is responsible for the isomerisation of a small portion of the higher energy molecular ions into the corresponding N-arylpyrrolidin-2-one ions. Copyright

Mild palladium-catalyzed C-H alkylation using potassium alkyltrifluoroborates in combination with MnF3

A Pd-catalyzed method for ligand-directed C-H alkylation with organoboron reagents is described. The combination of potassium organotrifluoroborates, MnF3, and a PdII catalyst effects pyridine and amide-directed C-H alkylation. These reactions proceed under mild conditions (25-40 C in weakly acidic media), are effective for installing methyl and 1 alkyl groups, and do not require promoters such as benzoquinone.

Copper-catalyzed N-arylation of amides using (S)-N-methylpyrrolidine-2- carboxylate as the ligand

(S)-N-methylpyrrolidine-2-carboxylate, a derivative of natural L-proline, was found to be an efficient ligand for the copper-catalyzed Goldberg-type N-arylation of amides with aryl halides under mild conditions. A variety of N-arylamides were synthesized in good to high yields.

Copper-catalyzed N-arylation of amides and azoles using phosphine-free hydrazone ligands

Phosphine-free hydrazone such as 1c was found to be an efficient ligand for the copper-catalyzed Goldberg-type N-arylation of amides and Ullmann-type N-arylation of azoles with aryl halides under mild conditions. A variety of N-arylamides and N-arylazoles were synthesized in good to high yields. Georg Thieme Verlag Stuttgart.