127500-89-4

Usage

Nitrile derivative

2-formyl-6-methoxyphenol The compound is derived from 2-formyl-6-methoxyphenol, with a nitrile group (CN) attached to the phenol structure.

Organic synthesis

Building block 2-(2-Formyl-6-methoxyphenoxy)acetonitrile is commonly used as a building block in the synthesis of complex organic molecules, allowing for the creation of various chemical structures.

Pharmaceutical research

Potential applications The compound has demonstrated potential in medicinal chemistry, serving as a promising scaffold for developing new drugs with therapeutic applications.

Nucleophilic reagent

Reactions with electrophiles 2-(2-Formyl-6-methoxyphenoxy)acetonitrile is known for its ability to act as a nucleophilic reagent, meaning it can donate electrons to other molecules, particularly electrophiles (electron-deficient species), in chemical reactions.

Diverse uses

Chemistry and pharmaceuticals The compound has a wide range of uses and applications in both the fields of chemistry and pharmaceuticals, making it a valuable asset for researchers and scientists.

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 107-14-2 chloroacetonitrile 
• 590-17-0 cyanomethyl bromide 

Relevant academic research and scientific papers

NHC-catalyzed green synthesis of functionalized chromones: DFT mechanistic insights and: In vitro activities in cancer cells

An efficient synthesis of 3-aminochromones and 3-alkylchromones by a N-heterocyclic carbene (NHC) catalyzed intramolecular hydroacylation reaction of corresponding salicylaldehyde derived nitriles and activated alkynes respectively in ionic liquids under microwave conditions is reported. This protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, and convenient operation using the commercially available thiazolium catalyst. The origin of the chemical reactivity of the NHC-catalyzed intramolecular hydroacylation reaction of nitriles is studied using Density Functional Theory (DFT). The results suggest that 3-aminochromone formation occurs via an acyl anion intermediate called a Breslow intermediate (INT2) through TS2. The Breslow intermediate (INT2) forms a carbon-carbon bond with the nitrile carbon to produce an imine intermediate INT3viaTS3, which further undergoes imine to amine tautomerism to give the end product. Some of the derivatives of 3-aminochromone are subjected to amine functionalization in one pot to obtain a library of compounds for anticancer activity. Among the investigated compounds, 2c (SVM-2), 4c (SVM-4) and 2d (SVM-9) show IC50 values of 5.18, 4.89 and 27.3 μM respectively in HeLa S3 cancer cells. Compound 5c (SVM-5) shows IC50 values of 13.3 and 14.2 μM in A549 and HeLa S3 cancer cells, respectively. Compounds 2c (SVM-2) and 4c (SVM-4) produce morphological changes and control the colony formation in HeLa S3 cells, which indicates that these small molecules are potential candidates for anticancer drugs.

INHIBITORS OF ALPHA-AMINO-BETA-CARBOXYMUCONIC ACID SEMIALDEHYDE DECARBOXYLASE

The present disclosure discloses compounds capable of modulating the activity of α- amino-β-carboxymuconic acid semialdehyde decarboxylase (ACMSD), which are useful for the prevention and/or the treatment of diseases and disorders associated with defects in NAD+ biosynthesis, e.g., metabolic disorders, neurodegenerative diseases, chronic inflammatory diseases, kidney diseases, and diseases associated with ageing. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament.

Regioselective Synthesis of Benzo[h][1,6]-naphthyridines and Chromenopyrazinones through Alkyne Cyclization

A regioselective approach to the synthesis of benzo[h][1,6]-naphthyridine and chromenopyrazinone derivatives was developed. The synthetic route to benzo[h][1,6]-naphthyridines involves the N-propargylation of aromatic aminobenzaldehydes, followed by reaction with propargylamine in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). For the synthesis of chromenopyrazine and chromenopyrazinone derivatives, the acetonitrile group was introduced to salicylaldehyde derivatives, and a DBU-promoted cyclization reaction between aldehydes and propargylamine gave the chromenopyrazines. The intramolecular heterocycloaddition reaction between the triple bond and the azadiene, which is formed as an intermediate, gave the desired structures.

Multicomponent synthesis of substituted and fused-ring imidazoles via phospha-münchnone cycloaddition

A new, one-pot synthesis of imidazoles from imines, acid chlorides, and N-nosyl imines or tethered nitriles is reported. The reaction is mediated by the phosphonite PPh(catechyl) and proceeds via regioselective cycloaddition with an in situ-generated phos

A step-economical route to fused 1,2,3-triazoles via an intramolecular 1,3-dipolar cycloaddition between a nitrile and an in situ generated aryldiazomethane

An intramolecular 1,3-dipolar cycloaddition strategy for rapid entry into triazole-fused heterocyclic compounds without recourse to the traditional Cu(1)-catalyzed azide-alkyne cycloadditions is described. Central to the strategy is the in situ generation of substituted diazomethanes in a two-step sequence from the corresponding aldehydes, which then undergo smooth cycloaddition with a cyano group to generate the desired fused 1,2,3-triazoles in good overall yields. The entire sequence can be carried out in a onepot operation.

N-heterocyclic carbene-catalyzed intramolecular aldehyde-nitrile cross coupling: An easy access to 3-aminochromones

(Figure presented) An immense effort has been made to develop an efficient strategy for the carbon-carbon bond formation between aldehyde and nitrile intramolecularly using an N-heterocyclic carbene catalyst to derive 3-aminochromone derivatives In good to excellent yields (80-95%).