7661-33-8

Usage

InChI:InChI=1/C10H10ClNO/c11-8-3-5-9(6-4-8)12-7-1-2-10(12)13/h3-6H,1-2,7H2

Upstream product

• 110-63-4 Butane-1,4-diol 
• 106-47-8 4-chloro-aniline 
• 40832-73-3 N-(4-chlorophenyl)piperidine 
• 27473-98-9 4-chloro-N-(4-chlorophenyl)butyramide 
• 2969-81-5 Ethyl 4-bromobutyrate 
• 14372-01-1 N-(4-chlorophenyl)cyclopropanecarboxamide 
• 616-45-5 2-pyrrolidinon 
• 1679-18-1 4-Chlorophenylboronic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4641-57-0 1-phenylpyrrolidin-2-one 
• 7661-18-9 4-bromo-N-(4-chlorophenyl)butyramide 

Downstream Products

• 96333-21-0 1-(4-chloro-phenyl)-5-hydroxy-pyrrolidin-2-one 
• 6943-00-6 1-(4-chlorophenyl)pyrrolidine-2,5-dione 
• 171054-81-2 1-(4-chlorophenyl)-3-ethoxycarbonyl-2-pyrrolidinone 

Relevant academic research and scientific papers

Synthetic method of N - aryl substituted lactam compound

The invention discloses a method. NSynthesis method of - aryl substituted lactam compound, and synthesis method thereof is promoted by tertiary butyl hydroperoxide and-tert-butyl hydroperoxideNMulti-step series reaction synthesis - aryl substituted saturated cyclic amine compoundN- Aryl substituted lactam compounds are simple and convenient to operate. The method has the advantages of no transition metal catalysis, wide substrate application range and the like, and is suitable for industrial production.

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.

Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles: Via the ring contraction and deformylative functionalization of piperidine derivatives

In this paper, a selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the cascade reactions of N-substituted piperidines is presented. Mechanistically, the formation of pyrrolidin-2-ones involves a domino process including the in situ formation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation and ipso-oxidation. On the other hand, 3-iodopyrroles are believed to be formed via the initial generation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation, dehydrogenation, iodination and aromatization. Interestingly, either pyrrolidin-2-ones or 3-iodopyrroles could be obtained selectively from the same substrates, and the selectivity was easily tuned by using a specific oxidant and additive.

Pyrrolidone compound synthesis method

The invention discloses a pyrrolidone compound synthesis method, and belongs to the technical field of organic synthesis. Saturated cyclic tertiary amine 1 is added into solvents, and heating reactionis performed in the presence of oxidizing agent, cupric salt, potassium hydrogen persulfate compound salt (Oxone) and oxygen mixture, additives, elementary iodine or iodated metal salt and the like to obtain pyrrolidone 2. According to the method, a pyrrolidone compound is synthesized by cascade reaction of oxidization retraction, decarbonylation and in-situ oxidization of saturated cyclic tertiary amine compounds, the method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like, and an economical, practical, green and environment-friendly novel method is provided for synthesis of the pyrrolidone compound.

Efficient Synthesis of N-Substituted 2,4-Azepandione Ring System as an Active Intermediate for Heterocyclic Syntheses

An improved efficient synthesis for 2,4-azepandiones (3, 8, and 14) could be achieved by a careful control of the reaction conditions to cyclize ethyl 4-(N-acetylarylamino) butanoate (1, 7, and 13), respectively. The ethyl 4-arylamino butanoate (9 or 12) was prepared by stirring the ethyl 4-bromobutanoate and substituted anilines at room temperature. Then, they were acetylated with acetyl chloride and triethylamine under the conditions that avoid the formation of 2-pyrrolidinone derivatives 10. Due to the rapid decomposition of the acetylated product (7 or 13) to its starting material (9 or 12), the reaction mixture is directly transferred without workup to the next cyclization step. The azepandione synthesis is favored by using a weak base at low temperature, where it is in a competition with the other modes of ring closure. The structures of the new compounds were supported by correct analytical and spectral data.

Synthesis and pharmacological evaluation of benzamide derivatives as potent and selective sigma-1 protein ligands

A series of novel benzamide-derived compounds was designed, synthesized and pharmacologically evaluated. Among all 37 synthesized compounds, two series were developed with the modulation of the nature, the position of atoms or groups on the benzamide scaffold, but also the nature of the amine group separated from the benzamide with 2, 3 or 4 methylene groups. In vitro competition binding assays against sigma proteins (sigma-1 S1R and sigma-2 S2R) revealed that most of them conferred S2R/S1R selectivity toward without cytotoxic effects on SY5Y cells, especially with the first series with compounds 7a-z. Some selected compounds were also evaluated for their agonist and antagonist activities on a panel of 40 receptors. Results showed the importance of the nature and the position with halogeno atom on the benzamide scaffold, the length chain but also the contribution of the hydrophobic part on the amine group. Among them, compounds 7i, w, y with Cl, CN or NO2 groups at the 4-position of the benzamide scaffold showed excellent affinity for S1R (Ki = 1.2–3.6 nM), selectivity for S2R (Ki up to 1400 nM) and high selectivity index (IC50(SY5Y)/Ki (S1R) ratio from 28 000 to 83 000). Futhermore, these compounds presented an excellent safety profile over 40 other receptors. These derivatives will be selected for further biological investigations.

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

Selective copper-catalyzed N-arylation of lactams with arylboronic acids under base- and ligand-free conditions

An oxidative copper-catalyzed cross-coupling of arylboronic acids with various ring-size lactams has been developed. The N-arylated lactams were obtained in moderate to excellent yields without any additional bases, ligands, or additives. This reaction shows complete selectivity for N-arylation of lactams in the presence of a hydroxyl group.

Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water

A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C2O4)·2H2O/N,N′-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.

Efficient ligand-free copper-catalyzed N-arylation of amides with aryl halides in water

A convenient and efficient protocol has been developed for the cross-coupling of amides and aryl iodides using a ligand-free copper(I) oxide catalyst in water. A variety of amide derivatives afforded the corresponding N-arylated products in moderate to good yields (up to 88%).