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Anion polarity-induced dual oxidation states in a dual-layered purely organic paramagnetic charge-transfer salt, (TTF)(3)(PO-CON(CH3)C2H4SO3)(2), where PO=2,2,5,5-tetramethyl-3-pyrrolin-1-oxyl free radical

The purely organic paramagnetic charge-transfer salt (TTF)(3)(PO-CON(CH3)C2H4SO3)(2) was prepared. The anisotropic anion forms a head-to-head arrangement in the anionic layer, giving dual donor layers with different oxidation states. SQUID magnetometry indicates that spins are localized not only on the free radical (PO) but also on both TTF layers.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Triarylborane catalysed N-alkylation of amines with aryl esters

The ability of halogenated triarylboranes to accept a lone pair of electrons from donor substrates renders them excellent Lewis acids which can be exploited as a powerful tool in organic synthesis. Tris(pentafluorophenyl)borane has successfully demonstrated its ability to act as a metal-free catalyst for an ever-increasing range of organic transformations. Herein we report the N-alkylation reactions of a wide variety of amine substrates including diarylamines, N-methylphenyl amines, and carbazoles with aryl esters using catalytic amounts of B(C6F5)(3). This mild reaction protocol gives access to N-alkylated products (35 examples) in good to excellent yields (up to 95%). The construction of a C-N bond at the propargylic position has also been demonstrated to yield synthetically useful propargyl amines. On the other hand, unsubstituted 1H-indoles and 1H-pyrroles at the C3/C2 positions afforded exclusively C-C coupled products. Extensive DFT studies have been employed to understand the mechanism for this transformation.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Group 6 Metal Carbonyl Complexes Supported by a Bidentate PN Ligand: Syntheses, Characterization, and Catalytic Hydrogenation Activity

We report on the preparation of a series of phosphorusnitrogen donor ligand complexes [M(CO)(4)(PN)], where M = Cr, Mo, W and PN is 2-(diphenylphosphino)-ethylamine. The organometallic compounds were readily obtained upon reacting the respective metal hexacarbonyls with equimolar amounts of the pertinent ligand in the presence of tetraethylammonium bromide. The PN-ligated metal carbonyls were fully characterized by standard spectroscopic techniques and X-ray crystallography. The ability of the title compounds to function as homogeneous hydrogenation catalysts was probed in the reduction of acetophenone and benzaldehyde derivatives to yield the corresponding alcohols. The reaction setup was easily assembled by simply combining the components in the autoclave on the bench outside an inert-gas-operated glovebox system

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Interaction of 1,5-substituted pyrrolin-2-ones with dichlorocarbene under phase transfer catalysis conditions

Treatment of 5-alkyl(aryl)-3H-pyrrolin-2-ones with dichlorocarbene under phase transfer catalysis conditions at 20-30 degreesC results in a cycloaddition of the carbene to the C=C bond followed by skeletal rearrangement.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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H-1 and C-13 2D NMR studies on substituted Delta 3-pyrrolin-2-ones

The H-1 and C-13 2D NMR studies of pyrrolinones derivatives were performed using the method of proton detected 2D H-1, C-13 correlation spectroscopy. HMQC and HMBC experiments were achieved in order to obtain the unambiguous assignment of the structures.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Construction of Vicinal Tetrasubstituted Stereogenic Centers via a Mannich-Type Organocatalyzed Addition of Delta(2)-Pyrrolin-4-ones to Isatin Imines

Racemic (2)-pyrrolin-4-ones (i.e. 4-pyrrolones), easily available in two steps from N-protected -amino acids, undergo organocatalysed asymmetric Mannich-type addition to isatin-derived ketimines to furnish the non-racemic oxindole-(2)-pyrrolin-4-one adducts, stereoselectively (up to 96% ee, dr15:1). The oxindole-pyrrolone products feature vicinal tetrasubstituted carbon stereocenters. The developed protocol has a broad substrate scope and tolerates diverse substituents at position C-5 in 4-pyrrolones and at positions N-1 and C-5/7 in isatin imines.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Inactivation of Thioglucosidase from Sinapis alba (White Mustard) Seed by Metal Salts

The glucosinolates which are specialized plant metabolites of Brassica vegetables are prone to hydrolysis catalyzed by an endogenous enzyme myrosinase (thioglycoside hydrolase, thioglucosidase) that exists in Brassica plant tissue causing volatile isothiocyanates release. Currently existing literature data on the inactivation of myrosinase is insufficient in particular for use in the analysis of volatile and odor compounds in vegetables rich in glucosinolates. In this study, the impact of different metal salts in effective inactivation of enzyme activity was investigated by solid-phase microextraction (SPME) and GC/MS system in aqueous samples and kohlrabi matrix. A saturated solution of calcium chloride which is commonly used to stop enzyme activity in plant tissue inactivates the myrosinase-glucosinolate system. However, even without the participation of myrosinase, it changes the reaction pathway towards nitrile formation. The model experiment shows that optimum efficiency in inhibition of the enzyme system shows iron(III) ions, silver ions, and anhydride sodium sulfate resulting in no volatile products derived from glucosinolates. However, in the kohlrabi matrix, the strongest enzyme inhibition effect was observed for silver salt resulting in no volatile products, also both anhydrous Na2SO4 and saturated CaCl2 solution seem to be useful inhibitors in flavor studies.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Insights on the Pseudo-Enantiomeric Properties of Bifunctional Cinchona Alkaloid Squaramide-Derived Organocatalyst

The use of pseudo enantiomers is a well-known method of achieving products of complementary stereochemistry. Only rarely can different enantiomers of a product be accessed without modulation of the catalyst. Recently, a system was reported wherein two different enantiomers of spirocycles were obtained by a cascade reaction of unsaturated pyrrolin-4-ones with mercaptoacetaldehyde catalyzed by a single optimized cinchona alkaloid squaramide-derived organocatalyst. It was originally proposed that the E/Z geometry of the unsaturated pyrrolin-4-one dictated the stereochemistry of the spirocycle product, but this was not investigated further. In the present work, we have investigated the nature of a pseudo-enantiomeric organocatalyst conformation applying density functional theory calculations for investigating the transition states for the reaction. Furthermore, the influence of the double-bond geometry of the pyrrolin-4-one has been studied beyond what is possible to test experimentally. The results provide a greater understanding for this class of reactions that may be applicable in future methodology development.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 1-(4-AMINOSULFONYLPHENYL)-5-ARYL-4-ACYL-3-HYDROXY-3-PYRROLIN-2-ONES

Interaction of 4-aminobenzenesulfamide with a mixture of an aromatic aldehyde and the methyl ester of an acylpyruvic acid was used to prepare 1-(4-aminosulfonylphenyl)-5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones. The antibacterial activity of these compounds was studied.

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Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem

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Chemical Research Letters, May 2021. As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world., Product Details of 107-97-1, Introducing a new discovery about 107-97-1, Name is Sarcosine, molecular formula is C3H7NO2, belongs to pyrrolines compound. In a document, author is Gao, Peng.

K2S2O8/TEMPO-Induced Cascade Oxidative Cyclization/1,2-Migration of Electron-Deficient Groups: Strategy for the Construction of 1H-Pyrrol-2(3H)-ones

A K2S2O8/TEMPO-induced oxidative cyclization of N-unprotected enaminoesters and enaminones that gave 1H-pyrrol-2(3H)-ones in good yields with broad functional group compatibility is reported. This method provides easy access to 1,2-carbon migration of ester or acyl group under transition-metal-free conditions.

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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem