76284-14-5

Upstream product

• 616-45-5 2-pyrrolidinon 
• 62-53-3 aniline 
• 63853-74-7 5-methoxypyrrolidin-2-one 
• 86976-26-3 5-(phenylthio)pyrrolidin-2-one 

Downstream Products

• 76284-15-6 5-(benzylamino)pyrrolidin-2-one 

Relevant academic research and scientific papers

Copper catalyzed oxidative cross-coupling of aromatic amines with 2-pyrrolidinone: A facile synthesis of N-aryl-γ-amino-γ-lactams

Synthesis of N-aryl-γ-amino-γ-lactams by oxidative coupling of aromatic amines with 2-pyrrolidinone using catalytic amount of CuO nanoparticles is described. The procedure has broad substrate scope, good yields, complete regioselectivity and catalyst recyclability.

Design, synthesis and antifungal activity of pterolactam-inspired amide Mannich bases

Pterolactam (5-methoxypyrrolidin-2-one) is a heterocycle naturally occurring in plants. In an attempt to identify antifungal agents, a series of novel Mannich bases of amide derivated from Pterolactam have been designed, synthesized and their antifungal activities were evaluated on a panel of nine fungal strains and three non albicans candida yeasts species which have demonstrated reduced susceptibility to commonly used antifungal drugs. A third of the target compounds exhibited good to high antifungal activities on at least one strain with EC50 lower than the control antifungal agent. N,N′-aminals derivated from Pterolactam proved to be good candidates for the development of biosourced fungicides, with compound 3o being the most broader-spectrum agent, active against five strains and devoted of any cytotoxicity.

Electrochemical Oxidative C?H/N?H Coupling between γ-Lactams and Anilines

A mild method for the direct C?H/N?H coupling between γ-lactams and anilines through electrochemical oxidation has been developed. The protocol proceeded smoothly without metal catalysts at room temperature to afford γ-substituted γ-lactams in good yields. It has been revealed that the quasi-divided cell which provided high current density on the anode was crucial for this reaction.

γ-Lactam-Based Antifungal Compounds against the Wheat Pathogen Zymoseptoria tritici

As new environmentally friendly and effective antifungal agents are deeply needed, efficient ecofriendly strategies were designed to access two series of compounds inspired from natural γ-lactams. Designed compounds were fully characterized and evaluated as antifungal candidates against Zymoseptoria tritici, the main pathogen on wheat crops. The targeted derivatives were prepared from natural resources using green solvents, simple procedures, and limited purification steps. These bio-inspired compounds revealed as good candidates for further development of efficient crop protection products. Indeed, the HIT compounds exhibited IC50 around 1 μg/mL and were more active than the references tebuconazole and bixafen towards some multidrug-resistant strains. Two dozen of derivatives have been obtained for each series and allowed to establish early structure-activity relationships useful for the development of next generation of γ-lactam derivatives with improved efficacy.

Cesium salts as superior catalysts for solvent-free modifications of biosourced pterolactam

γ-Lactam derivatives are widespread biologically active compounds, covering a large range of activities. Following our interest in both medicinal and green chemistries, we developed an original, cesium salts-mediated, scalable and solvent-free methodology to transform biosourced pyroglutamic acid and its derivatives to their N,N′-aminals, N,O,N,S-acetals and C5-substituted γ-lactams in good to excellent yields. This protocol is applicable to a large range of substrates, conducting to C5-substituted γ-lactam derivatives as potential new biologically active compounds.

FeCl3 catalyzed sp3 C-H amination: Synthesis of aminals with arylamines and amides

A simple and efficient amination of sp3 C-H bonds adjacent to a nitrogen atom in amides was introduced. The reaction was catalyzed by cheap and low toxic iron salt and used arylamines as nitrogen source. It provides a straightforward construction of acyclic aminals under mild conditions.

FeCl3 catalyzed sp3 C-H amination: Synthesis of aminals with arylamines and amides

A simple and efficient amination of sp3 C-H bonds adjacent to a nitrogen atom in amides was introduced. The reaction was catalyzed by cheap and low toxic iron salt and used arylamines as nitrogen source. It provides a straightforward construction of acyclic aminals under mild conditions.

Copper catalyzed oxidative cross-coupling of aromatic amines with 2-pyrrolidinone: A facile synthesis of N-aryl-γ-amino-γ-lactams

Synthesis of N-aryl-γ-amino-γ-lactams by oxidative coupling of aromatic amines with 2-pyrrolidinone using catalytic amount of CuO nanoparticles is described. The procedure has broad substrate scope, good yields, complete regioselectivity and catalyst recyclability.