81976-70-7

Upstream product

• 53162-40-6 1-(3-phenyl-acryloyl)-aziridine 
• 126437-20-5 1-cinnamoylaziridine 
• 950849-47-5 ethyl 4-azido-2-benzylbutanoate 
• 7732-18-5 water 
• 170304-80-0 methyl 2-(cyanomethyl)-3-phenylpropanoate 
• 1015069-81-4 tert-butyl 3-benzyl-2-oxopyrrolidine-1-carboxylate 
• 102-92-1 Cinnamoyl chloride 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 100-44-7 benzyl chloride 
• 68975-07-5 3-benzyltetrahydrofuran-2-one 

Downstream Products

• 119397-08-9 4-benzyl-5-ethoxy-2H 3,4-dihydropyrrole 
• 373356-31-1 3-benzyl-1-(ethoxycarbonylmethyl)-2-pyrrolidinone 
• 1361573-13-8 3-benzyl-N-(4-((6,7-dimethoxyquinolin-4-yl)oxy)-3-fluorophenyl)-2-oxopyrrolidine-1-carboxamide 
• 1361573-09-2 4-nitrophenyl 3-benzyl-2-oxopyrrolidine-1-carboxylate 
• 1015069-81-4 tert-butyl 3-benzyl-2-oxopyrrolidine-1-carboxylate 
• 178371-86-3 1-benzyl-3-(phenylmethyl)-2-oxo-pyrrolidine 
• 53101-33-0 3-benzyl-1-methylpyrrolidine-2-one 
• 1232954-02-7 t-butyl 3-benzyl-2-oxo-3-(trifluoromethyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction

A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.

Structure-based design of novel class II c-Met inhibitors: 1. Identification of pyrazolone-based derivatives

Deregulation of c-Met receptor tyrosine kinase activity leads to tumorigenesis and metastasis in animal models. More importantly, the identification of activating mutations in c-Met, as well as MET gene amplification in human cancers, points to c-Met as a

Direct acyl substitution of carboxylic acids: A chemoselective o- to N-acyl migration in the traceless staudinger ligation

A chlorophosphite-modified, Staudinger-like acylation of azides involving a highly chemoselective, direct nucleophilic acyl substitution of carboxylic acids is described. The reaction provides the corresponding amides with analytical purity in 32-97 % yield after a simple aqueous workup without the need for a pre-activation step. The use of chlorophosphites as dual carboxylic acid-azide activating agents enables the formation of acyl C-N bonds in the presence of a wide range of nucleophilic and electrophilic functional groups, including amines, alcohols, amides, aldehydes, and ketones. The coupling of carboxylic acids and azides for the formation of alkyl amides, sulfonyl amides, lactams, and dipeptides is described. Copyright

Intramolecular and intermolecular Schmidt reactions of alkyl azides with aldehydes

Despite recent advances in the use of alkyl azides in ring expansion reactions of ketones, there has been little work done on the corresponding chemistry of aldehydes. In the present study, the Lewis acid-promoted reactions of alkyl azides with aldehydes

Anticonvulsant and anxiolytic lactam and thiolactam derivatives

This invention relates to lactam and thiolactam derivatives having useful anticonvulsant and anxiolytic activity, pharmaceutical compositions containing these compounds and therapeutic applications using such compositions.

3,3-Dialkyl- and 3-alkyl-3-benzyl-substituted 2-pyrrolidinones: A new class of anticonvulsant agents

A series of 3,3-dialkyl- and 3-alkyl-3-benzyl-substituted 2- pyrrolidinones (lactams) have been prepared and evaluated for their anticonvulsant activities. In the pentylenetetrazole mouse seizure model, 3,3-diethyl lactam 7c and 3-benzyl-3-ethyl lactam 7j

Reactions of N-Cinnamoylaziridines by Generation of Aziridino Ketyls from Homolytic Cleavage of Michael Adducts

High yields of the pyrrolidinones 2a, b are obtained from N-cinnamoylaziridines 1a, b and the carbanion 'anthracene hydride' (anion of dihydroanthracene).Aziridino ketyls 3a, b are intermediates that probably arise by way of base-initiated homolytic fragm

HOMOLYTIC AZIRIDINE OPENING (AZA VARIANT OF CYCLOPROPYLCARBINYL-HOMOALLYL REARRANGEMENT) BY ADDITION OF TRIBUTYLTIN RADICAL TO N-ACYLAZIRIDINES. FACTORS CONTRIBUTING TO THE REGIOSELECTIVITY

AIBN initiated reaction of N-acylaziridines 1 with Bu3SnH in refluxing benzene provided products 5 and 8 of reductive ring opening.Yields (practically quantitative in most cases) fell drastically with steric hindrance of the addition of Bu3Sn to the acyl oxygen of 1.They depended to some extent on the experimental conditions for hydrogen capturing when aziridine homolysis provided a primary radical 3 or 6.The regioselectivity of (probably reversible) ring homolysis can be understood in terms of the stability of the arising radical (3, 6), of stereoelectronic control (e.g. 1i as compared to 1h) and of frontier orbital interactions (1j).A possible difference in bond lengths as explanation for the formation of the primary radical from 1j did not find support from an X-ray structure analysis of N-tosyl-2-methyl-aziridine 11.Isomeric products were obtained only twice (1i, 1j) with a dependence of the ratio 5j:8j on concentration and hydrogen isotope of Bu3SnH.No such dependence was found for the ratio 5:14 (reduction without and with an intervening cyclization of 3 leading to a pyrrolidone) obtained from the N-cinnamoylaziridine 1l.This ratio (1:9 for 1l and 1:3 for 1n) must reflect the E-Z isomers in 3.The observed preference for the formation of E-3 from 2 can be explained by stereoelectronic and steric effects.A cinnamoyl double bond in 5 was saturated depending on experimental conditions.

A MILD AND FACILE ROUTE TO ω-AMINO ESTERS

Lactim ethers are conveniently prepared from the corresponding lactam.The salt prepared by protonation with HCl or HBF4 is hydrolyzed in neutral water at ambient temperatures to give good yields of the ω-amino ester.

INTRAMOLECULAR RADICAL TRAPPING IN "SET" RING OPENING OF N-ENOYL AZIRIDINES. A NEW MECHANISTIC PROBE AND A NEW SYNTESIS OF PYRROLIDONES.

N-Acryloyl aziridines 1a-c form pyrrolidones 4a-c via electron attachment, homolytic ring cleavage of the intermediate ketyl, and intramolecular trapping of the radical by the C=C bond of the acryloyl moiety of 1a-c.