84713-70-2

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 459-73-4 GlyOEt*HCl 
• 623-33-6 glycine ethyl ester hydrochloride 

Downstream Products

• 103550-79-4 ethyl 2(4-chloro benzylidene)amino-4-pentenoate 
• 103550-80-7 2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-4-methyl-pent-4-enoic acid ethyl ester 
• 113845-94-6 3-(4-Chloro-phenyl)-2-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-3-hydroxy-propionic acid ethyl ester 
• 109918-43-6 2,5-Bis-(4-chloro-phenyl)-oxazolidine-4-carboxylic acid ethyl ester 
• 113845-91-3 2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester 
• 109918-44-7 2-(4-Chloro-phenyl)-5-(4-nitro-phenyl)-oxazolidine-4-carboxylic acid ethyl ester 
• 117470-84-5 2-{[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-amino}-3-phenyl-propionic acid ethyl ester 
• 55410-21-4 ethyl 2-aminobutyrate hydrochloride 
• 117770-60-2 ethyl 2-aminopent-4-enoate hydrochloride 
• 52031-05-7 2-amino-3-(4-chlorophenyl)propionic acid ethyl ester hydrochloride 
• 140939-51-1 2,2'-diamino-3,3'-o-phenylene-di-propionic acid 
• 204859-64-3 Ethyl-2-amino-3-(4'-chlorophenyl)prop-2-enoate 
• 126385-72-6 ethyl 2-[(4-chlorobenzylidene)amino]butanoate 

Relevant academic research and scientific papers

Nucleophilic reactivities of Schiff base derivatives of amino acids

Treatment of α-imino esters derived from glycine esters and benzophenone or benzaldehydes with potassium tert butoxide in DMSO gave persistent solutions of carbanions at 20 °C. The kinetics of their reactions with quinone methides and benzylidene malonates (reference electrophiles) have been followed photometrically under pseudo-first order conditions. The reactions followed second-order rate laws. Since addition of 18-crown-6 ether did not affect the reaction rates, the measured rate constants correspond to the reactions of the non-paired carbanions. Plots of the second-order rate constants against the electrophilicity parameters E of the electrophiles are linear, which allowed us to derive the nucleophile-specific parameters N and sN, according to the linear Gibbs energy relationship lg k2(20 °C) = sN(N + E). The Ph2C = N- and PhCH = N- groups act as very weak electron acceptors with the consequence that Ph2C = N-CH–-CO2R and PhCH = N-CH–-CO2R have a similar nucleophilicity as Ph-CH–-CO2Et, the anion of ethyl phenylacetate.

An efficient and facile access to highly functionalized pyrrole derivatives

A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research.

Synthesis of Pyrrole via a Silver-Catalyzed 1,3-Dipolar Cycloaddition/Oxidative Dehydrogenative Aromatization Tandem Reaction

Pyrroles are an important group of heterocyclic compounds with a wide range of interesting properties, which have resulted in numerous applications in a variety of fields. Despite the importance of these compounds, there have been few reports in the literature pertaining to the synthesis of pyrroles from simple alkenes using a one-pot sequential 1,3-dipolar cycloaddition/aromatization reaction sequence. Herein, we report the development of a benzoyl peroxide-mediated oxidative dehydrogenative aromatization reaction for the construction of pyrroles. We subsequently developed a one-pot tandem reaction that combined this new method with a well-defined silver-catalyzed 1,3-dipolar cycloaddition reaction, thereby providing a practical method for the synthesis of multisubstituted pyrroles from easy available alkenes. The mechanism of this oxidative dehydrogenative aromatization reaction was also examined in detail.

Tandem [3 + 2] cycloaddition/1,4-addition reaction of azomethine ylides and aza-o-quinone methides for asymmetric synthesis of imidazolines

An enantioselective synthesis of biologically important imidazolidines has been achieved via a tandem [3 + 2] cycloaddition/1,4-addition reaction of azomethine ylide and aza-o-quinone methides. With the use of this tool, various imidazolidine derivatives are obtained in good yields with excellent diastereoselectivities and enantioselectivities.

Cycloaddition reactions of glycine imine anions to phenylazocarboxylic esters - A new access to 1,3,5-trisubstituted 1,2,4-triazoles

Phenylazocarboxylic tert-butyl esters have recently been shown to be highly versatile building blocks due to their ability to undergo nucleophilic aromatic substitutions under mild conditions, particularly well with [18F]fluoride, and to act as precursors for aryl radicals. In this article, we now report first examples for cycloaddition reactions to phenylazocarboxylates. In a one-pot reaction with readily accessible glycine imines, a variety of highly substituted 1,2,4-triazoles could be obtained.

Cu(I)-Catalyzed Highly Enantioselective [3 + 3] Cycloaddition between Two Different 1,3-Dipoles, Phthalazinium Dicyanomethanides and Iminoester-Derived Azomethine Ylides

(Chemical Equation Presented). The Cu(I)-catalyzed highly enantioselective [3 + 3] cycloaddition between two different 1,3-dipoles, phthalazinium dicyanomethanides and iminoester-derived azomethine ylides, has been achieved under mild reaction conditions, providing novel chiral heterocyclic compounds, 2,3,4,11b-tetrahydro-1H-pyrazino[2,1-a]phthalazine derivatives, in high yields with excellent diastereo- and enantioselectivies (up to 99% yield, 99% ee, >20:1 dr).

Metal-catalyzed [6 + 3] cycloaddition of tropone with azomethine ylides: A practical access to piperidine-fused bicyclic heterocycles

The first metal-catalyzed [6 + 3] cycloaddition of tropone with azomethine ylides has been developed. With the use of a chiral ferrocenylphosphine- copper(I) complex as the catalyst, the asymmetric variant of the [6 + 3] cycloaddition has also been successfully achieved. The reactions proceeded smoothly under mild conditions, affording piperidine-fused bicyclic heterocycles in moderate to high yields with good to excellent diastereo-and enantioselectivies. The procedures are operationally simple and the catalysts are cheap and readily accessible, thus providing a practical approach to piperidine-fused bicyclic heterocycles.

Preparation of renieramycin left-half model compounds

Model compounds of the left-half of renieramycins, which are anticancer marine natural products having an α-aminonitrile functionality, were prepared from phenylalanine derivatives. The key step of the transformation is the stereospecific construction of 1,3-cis stereochemistry via an exomethylene intermediate. The stereoselective α-aminonitrile formation under kinetically controlled conditions is also discussed. The initial cytotoxicity profiles are presented.

Enantioselective copper-catalyzed [3+3] cycloaddition of azomethine ylides with azomethine imines

The more dipoles, the merrier: An asymmetric [3+3] cycloaddition of azomethine ylides derived from imines 1 with azomethine imines 2 in the presence of a chiral ferrocenylphosphine-copper catalyst afforded highly functionalized heterocyclic products 3 in high yield with excellent enantio- and diastereoselectivity (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). The 1,3-dipolar reaction partners can be readily prepared from aldehydes. Copyright

METHOD FOR PRODUCING OPTICALLY ACTIVE 1-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ESTER

1-Amino-2-vinylcyclopropanecarboxylic acid ester, which is useful as a synthetic intermediate of pharmaceuticals, can be produced by a process of producing 1-amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (4): including a step of hydrolysis of an optically active 1-N-(arylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester represented by formula (3): which is obtained by reacting an N-(arylmethylene)glycine ester represented by formula (1): with a compound represented by formula (2): in the presence of a base and an optically active quaternary ammonium salt.