22217-78-3

Usage

Uses

Used in Pharmaceutical Industry:
5-(4-CHLORO-PHENYL)-3,4-DIHYDRO-2H-PYRROLE is used as a therapeutic agent for the treatment of cognitive disorders such as Alzheimer's disease and schizophrenia. Its ability to modulate neurotransmitter systems in the brain makes it a promising candidate for further research and development in these areas.

Upstream product

• 189079-77-4 4-Azido-1-(4-chloro-phenyl)-butan-1-one 
• 616-45-5 2-pyrrolidinon 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 7347-71-9 N-[4-(4-chloro-phenyl)-4-oxo-butyl]-phthalimide 
• 29480-09-9 1-(4-chlorophenyl)cyclobutan-1-ol 
• 74-11-3 para-chlorobenzoic acid 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 40877-09-6 4-chloro-1-(4-chlorophenyl)butan-1-one 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 14774-78-8 4-chlorophenyl lithium 
• 106-39-8 bromochlorobenzene 
• 628-20-6 4-Chlorobutyronitrile 
• 40394-87-4 4-(4-chloro-phenyl)-4-oxo-butyronitrile 

Downstream Products

• 189079-86-5 4,4-Dichloro-5-(4-chloro-phenyl)-3,4-dihydro-2H-pyrrole 
• 189079-90-1 4,4-Dibromo-5-(4-chloro-phenyl)-3,4-dihydro-2H-pyrrole 
• 1217651-75-6 (S)-2-(4-chlorophenyl)-pyrrolidine 
• 1217831-54-3 (R)-2-(4-chlorophenyl)-pyrrolidine 
• 76532-30-4 6-[2-(4-Chloro-phenyl)-pyrrolidin-1-yl]-pteridine-2,4-diamine 
• 38944-14-8 2-(4-chlorophenyl)pyrrolidine 
• 111399-31-6 1-methyl-2-(4-chlorophenyl)-1-pyrrolinium trifluoromethanesulfonate 

Relevant academic research and scientific papers

Easy one-pot access to substituted 2-phenylpyrrolines from 2-pyrrolidinone

An easy access to 2-aryl pyrrolidines is the reduction, stereospecific or not, of the corresponding 2-aryl-pyrroline (5-aryl-3,4-dihydro-2H-pyrrole). Preparation of the latter has been carried out from 2-pyrrolidinone using an easy one-pot two-step method

Iron-Catalyzed Ring Expansion of Cyclobutanols for the Synthesis of 1-Pyrrolines by Using MsONH3OTf

The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONH3OTf) has been developed. This one-pot procedure achieves C–N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthes

Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions

We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).

Design, synthesis and biological evaluation of N-hydroxy-aminobenzyloxyarylamide analogues as novel selective κ opioid receptor antagonists

Aminobenzyloxyarylamide derivatives 1a-i and 2a-t were designed and synthesized as novel selective κ opioid receptor (KOR) antagonists. The benzoyl amide moiety of LY2456302 was changed into N-hydroxybenzamide and benzisoxazole-3(2H)-one to investigate whether it could increase the binding affinity or selectivity for KOR. All target compounds were evaluated in radioligand binding assays for opioid receptor binding affinity. These efforts led to the identification of compound 1c (κ Ki = 179.9 nM), which exhibited high affinity for KOR. Moreover, the selectivity of KOR over MOR and DOR increased nearly 2-fold and 7-fold, respectively, compared with (±)LY2456302.

Intramolecular Csp3-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

The intramolecular Csp3-H and/or C-C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp3-H and/or C-C bond cleavage. Two C-N single bonds or a CN double bond are efficiently constructed in these transformations. The carbocation mechanism differs from the reported metal nitrene intermediates and therefore enables metal-free and new transformation.

Method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol

The invention discloses a method for synthesizing pyrroline compounds through iron-catalyzed amino alcohol and enol. In the atmosphere of inert gas, the amino alcohol and the enol serve as raw materials, potassium tert-butoxide is used as alkali, a series

Palladium-catalysed anti-Markovnikov selective oxidative amination

In recent years, the synthesis of amines and other nitrogen-containing motifs has been a major area of research in organic chemistry because they are widely represented in biologically active molecules. Current strategies rely on a multistep approach and require one reactant to be activated prior to the carbon-nitrogen bond formation. This leads to a reaction inefficiency and functional group intolerance. As such, a general approach to the synthesis of nitrogen-containing compounds from readily available and benign starting materials is highly desirable. Here we present a palladium-catalysed oxidative amination reaction in which the addition of the nitrogen occurs at the less-substituted carbon of a double bond, in what is known as anti-Markovnikov selectivity. Alkenes are shown to react with imides in the presence of a palladate catalyst to generate the terminal imide through trans-aminopalladation. Subsequently, olefin isomerization occurs to afford the thermodynamically favoured products. Both the scope of the transformation and mechanistic investigations are reported.

Highly effective asymmetric hydrogenation of cyclic N -alkyl imines with chiral cationic Ru-MsDPEN catalysts

A range of cyclic N-alkyl imines were efficiently hydrogenated by using a chiral cationic Ru(η6-cymene)(MsDPEN)(BArF) complex (MsDPEN = N-(methanesulfonyl)-1,2-diphenylethylenediamine) in high yields and up to 98% ee. A one-pot synthesis of chiral 2-phenylpyrrolidine via reductive amination was also developed.

Iridium-catalyzed enantioselective hydrogenation of cyclic imines

A catalytic complex made from [Ir(COD)Cl]2 [di-μ-chloro- bis(1,5-cyclooctadiene)diiridium(I)] precursor and (S,S)-f-Binaphane ((R,R)-1,1′-bis{(R)-4,5-dihydro-3H-dinaphtho[1,2-c:2′,1′-e] phosphepino}ferrocene) ligand effectively catalyzed the en

Hammett correlation of nornicotine analogues in the aqueous aldol reaction: Implications for green organocatalysis

(Chemical Equation Presented) A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with ρ = 1.14 (R2 = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organocatalyst.