104310-44-3

Upstream product

• 104310-28-3 4,4-Dichloro-5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 98-16-8 3-trifluoromethylaniline 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 4931-66-2 methyl 5-oxopyrrolidine-2-carboxylate 
• 149-87-1 Pyroglutamic acid 
• 104310-24-9 2,2,4-trichloro-4-methoxycarbonyl-butyric acid chloride 

Downstream Products

• 104310-45-4 1-(3-Trifluoromethyl-phenyl)-pyrrolidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Exploring isoxazoles and pyrrolidinones decorated with the 4,6-dimethoxy-1,3,5-triazine unit as human farnesyltransferase inhibitors

Unprecedented triazinyl-isoxazoles were afforded via an effective cycloaddition reaction between nitrile oxides and the scarcely described 2-ethynyl-4,6-dimethoxy-1,3,5-triazine as dipolarophile. The biological evaluation of the newly synthesized compounds showed that the inhibition of human farnesyltransferase by zinc complexation could be improved with triazine-isoxazole moieties. The replacement of the isoxazole unit by a pyrrolidin-2-one was detrimental to the inhibitory activity while the pyrrolidin-2-thione derivatives conserved the biological potential. The potential of selected compounds to disrupt protein farnesylation in Chinese hamster ovary (CHO) cells transfected with pEGFP-CAAX was also evaluated.

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp2-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.

Studies on pyrrolidinones. On the application of copper-catalyzed arylation of methyl pyroglutamate to obtain a new benzo[de]quinoline scaffold

Optimized conditions for copper-catalyzed N-arylation of methyl pyroglutamate are described. These studies permitted the synthesis of methyl N-naphthylpyroglutamate, which was then cyclized to a ketone. The known dehydration of amidoketones by PPA was extended to this new scaffold to lead to a novel condensed benzo[de]quinoline with potential antioxidative activity.

CONVENIENT APPROACHES TO HETEROCYCLES VIA COPPER-CATALYSED ADDITIONS OF ORGANIC POLYHALIDES TO ACTIVATED OLEFINS

An efficient method for the synthesis of 2,3-dichloro-5-substituted (Cl, CF3, alkyl) pyridines 29 starting from the 1:1 adducts of the copper-catalysed addition of chloral or the corresponding 2,2-dichloroaldehydes to acrylonitrile is presented.Proper choice of experimental conditions allows the preparation of 29 in one-pot process.Similarly, the CuCl-catalysed reaction of methyl itaconate with several trichloromethyl compounds R-CCl3 gives 6-R-substituted 2-pyrone derivatives 40 via dehalogenation and subsequent thermal ring closure of the primary 1:1-adducts. The new electrophilic 2-pyrone 40b undergoes-cycloaddition reactions with inverse electron demand with a number of olefins and acetylenes, allowing thereby regioselective transfer of a trifluoromethyl group from a simple Freon derivative (1,1,1-trichloro-2,2,2-trifluoroethane) into more complex organic molecules.Finally, the 1:1-adduct of trichloroacetylchloride with methyl acrylate allows a very covenient synthesis of novel N-substituted derivatives 66 of pyroglutamic acid as well as of proline.