3009-97-0

Usage

Uses

N-Phenylglycinonitrile is a useful building block used in the preparation of purine derivatives with ability to inhibit protein kinases by competitive displacement of ATP.

InChI:InChI=1/C8H8N2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,10H,7H2

Upstream product

• 107-14-2 chloroacetonitrile 
• 62-53-3 aniline 
• 50-00-0 formaldehyd 
• 74-90-8 hydrogen cyanide 
• 149-44-0 rongalite 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 540-61-4 2-aminoacetonitrile 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 151-50-8 potassium cyanide 
• 590-17-0 cyanomethyl bromide 
• 7677-24-9 trimethylsilyl cyanide 
• 13314-99-3 N-(anilomethyl)succinimide 
• 64-17-5 ethanol 
• 7732-18-5 water 

Downstream Products

• 21969-70-0 2-anilinoacetamide 
• 827-51-0 N-nitroso-N-phenyl-glycine nitrile 
• 98594-16-2 2-anilino-acetamide oxime 
• 18138-16-4 N-phenyl-thioglycine amide 
• 4432-90-0 bis(2-phenylaminoethyl)amine 
• 219598-39-7 2,2',2''-tris(phenylamino)triethylamine 
• 1664-40-0 N-(2-aminoethyl)benzeneamine 
• 103-01-5 N-Phenylglycine 
• 14101-08-7 N-benzoyl-N-phenylaminoacetonitrile 
• 135481-41-3 N-(2-cyanoethyl)-N-(cyanonmethyl)aniline 
• 86273-74-7 N-phenyl-N,N-bis(cyanomethyl)amine 
• 22985-17-7 N-Cyanomethyl-2-methyl-3,5-dinitro-N-phenyl-benzamide 
• 22977-84-0 N-(4-Amino-3,5-dichlorbenzoyl)-N-phenylcyanamid 
• 22977-96-4 2-Chloro-N-cyanomethyl-4-nitro-N-phenyl-benzamide 

Relevant academic research and scientific papers

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

Nano cobalt-copper ferrite catalyzed regioselective α-C(sp3)–H cyanation of amines: Secondary, tertiary, and drug molecules

Oxidative cyanation of sp3C–H bonds at the α position of amines was achieved using CoCuFe2O4 as a catalyst and NaCN as an inexpensive cyanide source at room temperature. CoCuFe2O4 was found to be an active catalyst for Csp [3]-Csp coupling, efficiently delivering valuable α-aminonitriles from tertiary/secondary amines in good yields. The corresponding products were obtained with high selectivity toward α position. In addition, functional group tolerance offered the opportunity for application in late-stage functionalization of biologically active molecules. This transformation proceeds convenient on a gram-scale, and the catalyst can be reused for several runs with consistent catalytic activity.

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

Covalently hooked EOSIN-Y in a Zr(IV) framework as visible-light mediated, heterogeneous photocatalyst for efficient C–H functionalization of tertiary amines

Herein, we report the synthesis of a novel heterogeneous photo-catalyst by utilizing post-synthetic modification of an amine functionalized Zr(IV) metal-organic framework (UiO-66-NH2) through covalent hooking of EOSIN-Y via dehydrating coupling. The characterization of the catalyst was accomplished by FT-IR, XRD, BET surface analysis, TGA, as well as TEM, SEM, XPS, DRS-UV–visible, and NMR spectroscopy, confirming successful covalent linking of EOSIN-Y with the pendent –NH2 functionality in the framework. That post-modified EY@UiO-66-NH2 acts as simple and green visible light mediated photo-catalyst for the C–H activation of tertiary amines with excellent yields. Importantly, the activity of dye incorporated heterogeneous photo-catalyst is found superior to that for the homogeneous photo-catalyst EOSIN-Y. Thus, separation difficulty of homogeneous catalysis, as well as the environmental adverse effects of toxic EOSIN-Y can be excluded by developing such photo-catalyst. Moreover, EY@UiO-66-NH2 catalyst could be consistently recycled up to 10 cycles, without any significant loss in activity. Based on literature report and experimental findings, we also propose a plausible mechanism for the reaction.

A process for preparing aniline base second grade nitrile system and method

The invention relates to a method for preparing n-system and method. First, the invention provides an improved pipe-type continuous reaction system, the system through the flow or mass of material entering the system of the shunt to measure to control the material reaction, and the introduction of a new feeding mode and take with a mixing element of the reactor, so that the system can enhance the mass transfer of the reaction raw materials, the reaction efficiency is improved. In addition, the invention also provides a method for preparing n-method, the method utilizing the above-mentioned reaction system to realize, this method can reduce the hydroxy acetonitrile to aniline disubstituted formation of impurities, can also reduce the hydroxy acetonitrile in the alkaline catalyst under the influence of the polymerization, the product quality is improved and the reaction yield.

Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes

Emerging applications in the field of chemical biology are currently limited by the lack of bioorthogonal reactions allowing both removal and linkage of chemical entities on complex biomolecules. We recently discovered a novel reaction between iminosydnones and strained alkynes leading to two products resulting from ligation and fragmentation of iminosydnones under physiological conditions. We now report the synthesis of a panel of substituted iminosydnones and the structure reactivity relationship between these compounds and strained alkyne partners. This study identified the most relevant substituents, which allow to increase the rate of the transformation and to develop a bifunctional cleavable linker with improved kinetics.

A aniline acetate preparation method

The invention discloses an anilino-acetate preparation method, which comprises the steps of synthesis of n-phenylglycinenitrile, separation of n-phenylglycinenitrile, recovery of hydroxy acetonitrile and preparation of anilino-acetate. The preparation technology has the advantages of economy and environmental protection, hydroxy acetonitrile and aniline consumption can be reduced, waste water generation amount is reduced, flow is simplified, and product quality is increased.

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

High-yielding automated convergent synthesis of no-carrier-added [11C-carbonyl]-labeled amino acids using the strecker reaction

A new variant of the Strecker synthesis using no-carrier-added [11C]cyanide for the synthesis of radiolabeled amino acids is described. The protocol is fully automated using a radiochemistry synthesis module and applied to the production of a number of new PET radiotracers. [11C-Carbonyl]sarcosine, [11C-carbonyl]methionine, [11C-carbonyl]-N-phenylglycine, and [11C-carbonyl]glycine are all synthesized in moderate to good radiochemical yields. The synthesis of [11C-carbon-yl]sarcosine has been validated for production of doses for clinical use, and preliminary evaluation of the new radiotracer in PC3 tumor-bearing mice is also reported.