218168-58-2

Usage

Uses

Used in Pharmaceutical Industry:
Glycine, N-(4-cyanophenyl)-, ethyl ester is used as a synthetic reagent for the production of dihydroquinazolines and quinolines. These compounds are important in the pharmaceutical industry as they serve as the core structure for various drugs with diverse therapeutic applications, including antihypertensive, antiplatelet, and anticancer agents. The use of this ester in the synthesis process allows for the creation of these biologically active molecules with improved efficiency and selectivity.
Used in Chemical Research:
In the field of chemical research, Glycine, N-(4-cyanophenyl)-, ethyl ester is utilized as a key intermediate in the synthesis of complex organic molecules. Its unique structure and reactivity make it a valuable tool for exploring new chemical reactions and developing novel synthetic pathways. This contributes to the advancement of organic chemistry and the discovery of new compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 873-74-5 4-Aminobenzonitrile 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 1441049-11-1 diethyl 6-cyano-3-(4-cyanophenyl)-3,4-dihydroquinazoline-2,4-dicarboxylate 
• 429658-95-7 3-({2-[(4-carbamimidoylphenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid ethyl ester 

Relevant academic research and scientific papers

A series of robust metal-porphyrinic frameworks based on rare earth clusters and their application in N-H carbene insertion

We herein report a series of microporous metal-porphyrinic frameworks (MPFs), denoted as NUPF-2M, based on rare earth (RE) clusters. NUPF-2M represent the first examples of RE cluster-based MPFs, possessing a rarely seen shp-a topology and exhibiting high thermal and thermal stabilities. After a post-metallization process with FeCl3, NUPF-2M is catalytically active as an efficient heterogeneous catalyst for intermolecular N-H carbene insertion.

Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams

A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.

Molecular Oxygen-Mediated Radical Alkylation of C(sp3)-H Bonds with Boronic Acids

A direct and site-specific alkylation of (sp3)C-H bond with aliphatic boronic acid was achieved. By simply heating glycinates and amines together with alkylboronic acids under an oxygen atmosphere, a variety of unnatural α-amino acids and peptides could b

Preparation method for dabigatran etexilate

The invention provides a method for preparing dabigatran etexilate. The method comprises the following steps: A) subjecting a compound as shown in a formula I and a compound as shown in a formula II to a reaction in an inert solvent so as to obtain a compound as shown in a formula III, wherein the compound as shown in the formula II comprises an R which is one selected from the group consisting of methyl, ethyl, propyl or isopropyl; B) subjecting the compound as shown in the formula III to activation through a hydrogen chloride solution in an inert solvent, and carrying out a reaction of the activated material and an ammonium salt so as to obtain a product IV; and C) subjecting a compound as shown in a formula IV and a compound as shown in a formula V to a reaction under the action of an acid-binding agent so as to obtain dabigatran etexilate VI. The method provided by the invention has the advantages of low cost, high yield, mild reaction conditions, avoidance of using unstable reagents, etc.

Dual role of Cu2O nanocubes as templates and networking catalysts for hollow and microporous Fe-porphyrin networks

Cu2O nanocubes were used for the synthesis of hollow and microporous Fe porphyrin networks (H-MFePN). In this synthesis, Cu2O nanocubes performed not only as networking catalysts but also as shape controlling templates. MFePN were formed on the surface of the Cu2O nanocubes through azide-alkyne cycloaddition of tetrakis(4-ethynylphenyl) Fe-porphyrin with 1,4-diazidobenzene. H-MFePN showed excellent catalytic activities in carbene insertion into N-H bonds, maintaining their activities during five recycle tests.

Iron-catalyzed oxidative tandem reactions with TEMPO oxoammonium salts: Synthesis of dihydroquinazolines and quinolines

A straightforward iron-catalyzed divergent oxidative tandem synthesis of dihydroquinazolines and quinolines from N-alkylanilines using a TEMPO oxoammonium salt as a mild and nontoxic oxidant has been developed. Fe(OTf) 2 was the Lewis acid cata

Iridium porphyrin catalyzed N-H insertion reactions: Scope and mechanism

Ir(TTP)CH3 catalyzed N-H insertion reactions between ethyl diazoacetate (EDA) or methyl phenyldiazoacetate (MPDA) and a variety of aryl, aliphatic, primary, and secondary amines to generate substituted glycine esters with modest to high yields. Aniline substrates generally gave yields above 80%, with up to 105 catalyst turnovers, and without slow addition of the diazo reagent. Good yields were also achieved with aliphatic amines, though higher catalyst loadings and slow addition of the amine were necessary in some cases. Primary amines reacted with EDA to generate both single- and double-insertion products, either of which could be produced selectively in high yield with the proper choice of stoichiometric ratios and reaction temperature. Notably, mixed trisubstituted amines, RN(CH2CO2Et) (CHPhCO2Me), were generated from the insertion of 1 equiv of EDA and 1 equiv of MPDA into primary amines. The N-H insertion mechanism was examined using substrate competition studies, trapping experiments, and multiple spectroscopic techniques. Substrate competition studies using pairs of amines with EDA or MPDA revealed Hammett correlations with respective slopes of ρ = 0.15 and ρ+ = -0.56 as well as kinetic isotope ratios of k H/kD = 1.0 ± 0.2 and 2.7 ± 0.2. Competitive amine binding to the iridium center was demonstrated by kinetics and equilibrium binding studies. Equilibrium binding constants ranged from 102 to 105. Monitoring the reaction by absorption spectroscopy revealed a transient metalloporphyrin complex. The lifetime of this species was dependent on the nature of the amine substrate, which suggests that the catalytic cycle proceeds through a metal-ylide intermediate.

A RuII-N-heterocyclic carbene (NHC) complex from metal-metal singly bonded diruthenium(I) precursor: Synthesis, structure and catalytic evaluation

A mononuclear Ru(II)-N-heterocyclic carbene (NHC) complex [Ru II(CO)2(κ2C,N-BIN)(H2O)Br] [OTf] (OTf = trifluoromethane sulphonate) (1) has been synthesized in high-yield by the oxidative cleavage of the metal-metal singly-bonded diruthenium(I) precursor [Ru2(CO)4(CH3CN)6(OTf) 2] with 1,8-naphthyridine functionalized NHC precursor 1-benzyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazolium bromide (BIN·HBr) at room temperature. Compound 1 catalyzes transfer hydrogenation of ketones to alcohols, and carbene-transfer from ethyl diazoacetate to a variety of substrates. It is shown to be an excellent catalyst for the insertion of carbene into the O-H and N-H bonds of alcohols and amines.

Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: Synthetic uses and mechanistic insights

A thorough mechanistic investigation has been performed on the reactions of primary and secondary amines with diazoacetates, which proceed uniquely quickly and efficiently when catalyzed by iron(III) corroles and porphyrins. Two major differences in relation to other metal-based catalysts are that the iron complexes are not poisoned by excess amine and that metal-carbene intermediates are apparently not involved in the reaction pathway. The results instead point towards nitrogen ylide intermediates formed by nucleophilic attack of the amines on diazoacetate-coordinated iron complexes. Nitrogen ylides are also formed when allyl- and propargylsubstituted tertiary amines react with diazoacetates, a scenario that smoothly leads to 2,3-rearrangement reaction products with catalytic amounts of the iron(III) complexes. Similar findings regarding the superiority of the iron-(III) complexes (in terms of catalyst loading, chemical yields, and reaction conditions) were obtained with thiols (S-H insertion) and sulfides (2,3-rear-rangement reactions), which suggest similar mechanisms operate in these cases.

Iron corroles and porphyrins as very efficient and highly selective catalysts for the reactions of α-diazo esters with amines

Iron corroles and porphyrins catalyze the reactions of amines with ethyl diazoacetate extremely efficiently, leading to complete and rapid conversion into N-substituted glycine ethyl esters by simultaneous addition of the substrates to the catalysts. The selectivity toward activation of the NH bonds is remarkable and quite different from other catalysts. Georg Thieme Verlag Stuttgart.