54660-08-1

Usage

Chemical Properties

beige crystalline powder

InChI:InChI=1/C10H10FNO/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 
• 371-40-4 4-fluoroaniline 
• 4280-36-8 (4-fluorophenyl)piperidine 
• 616-45-5 2-pyrrolidinon 
• 1765-93-1 4-fluoroboronic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 352-34-1 4-fluoro-1-iodobenzene 

Downstream Products

• 1062574-82-6 [1-(4-fluoro-phenyl)-2-oxo-pyrrolidin-3-yl]-phosphonic acid diethyl ester 
• 4280-34-6 N-(4-fluorophenyl)tetrahydropyrrole 
• 852227-90-8 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidineate 

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.

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.).

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.

α-Aminoamides as ligands in Goldberg amidations

α-Aminoamides are shown to be useful as ligands in Goldberg amidations. A number of α-aminoamides are examined and the importance of substitution on the α-aminoamides is explored. Acetamide is focused on as the nucleophilic coupling partner due to its low cost, stability and convenience as a protecting group. The initial substrate scope for these catalysts is explored and includes electronically activated and deactivated aryl bromides, however o-substituted aryl bromides are problematic.

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%).