90617-02-0

Basic information

• Product Name: N-(4-CYANOPHENYL)-2-METHYLACRYLAMIDE
• Synonyms: N-(4-CYANOPHENYL)-2-METHYLACRYLAMIDE
• CAS NO: 90617-02-0
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.21
• Mol File: 90617-02-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-CYANOPHENYL)-2-METHYLACRYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-CYANOPHENYL)-2-METHYLACRYLAMIDE(90617-02-0)
• EPA Substance Registry System: N-(4-CYANOPHENYL)-2-METHYLACRYLAMIDE(90617-02-0)

Safety Data

• Hazardous Substances Data: 90617-02-0(Hazardous Substances Data)

Upstream product

• 873-74-5 4-Aminobenzonitrile 
• 920-46-7 Methacryloyl chloride 

Downstream Products

• 1287759-57-2 N-(4-cyanophenyl)-N,2-dimethyl-2-propenamide 
• 1588429-82-6 1, 3-dimethyl-2-oxo-3-((phenylsulfonyl)methyl)indoline-5-carbonitrile 

Relevant articles and documents

Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones

Metal- and additive-free photoredox cyclization of N-arylacrylamides is herein reported that provides a concise access to the formation of dihydroquinolinones. In this protocol, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. This reaction system features exclusive 6-endo-trig cyclization selectivity with a generally good yield of a range of functionalized dihydroquinolinones and dihydrobenzoquinolinones. Mechanistical studies reveal the feasibility of both 1,3-H shift and intersystem crossing of the diradical intermediate.

N-Heterocyclic Carbene-Catalyzed Truce-Smiles Rearrangement of N-Arylacrylamides via the Cleavage of Unactivated C(aryl)-N Bonds

We report on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, in which an unactivated C(aryl)-N bond is cleaved, leading to the formation of a new C(aryl)-C bond. The key to the success of this reaction is the

A benzene-bridged divanadium complex-early transition metal catalyst for alkene alkylarylation with PhI(O2CR)2viadecarboxylation

The synthesis, structure and catalytic activity of a benzene-bridged divanadium complex were comprehensively studied. The reduction of (Nacnac)VCl2(1) (Nacnac = (2,6-iPr2C6H3NCMe)2HC) supported by β-diketiminate with potassium graphite (KC8) by employing benzene as the solvent allows access to the benzene-bridged inverted-sandwich divanadium complex (μ-η6:η6-C6H6)[V(Nacnac)]2(2a), which can catalyze alkene alkylarylation with hypervalent iodine(iii) reagents (HIRs)viadecarboxylation to generate regioselectively diverse indolinones. Furthermore, the mild nature of this reaction was amenable to a wide range of functionalities on alkenes and HIRs. Mechanistic studies revealed a relay sequence of decarboxylative radical alkylation/radical arylation/oxidative re-aromatization.

Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICF3Cl

Trifluoromethylation-triggered cyclization of alkenes provides a useful route to CF3-containing cyclic compounds. Current approaches to generate CF3-based initiators from a CF3 source require a catalyst or an activator. This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides. A new domino biscyclization of dienes has been developed leading to trifluoroethylated tetrahydroindenoquinolinones with chemo- and stereo-selectivity.

Disulfides as Sulfonylating Precursors for the Synthesis of Sulfone-Containing Oxindoles

The first facile one-pot synthesis of sulfone-containing oxindoles with easily accessible disulfides as the sulfonylating precursors is described. This reaction occurs smoothly under transition metal-free conditions and shows excellent functional group tolerance, allowing the facile and efficient green synthesis of various sulfone-containing oxindoles in aqueous solution. Preliminary mechanistic studies reveal that both water (H2O) and potassium persulfate (K2S2O8) can be the oxygen source of the sulfone groups in the products. (Figure presented.).

Light-induced BiOBr nanosheets accelerated highly regioselective intermolecular trifluoromethylation/arylation of alkenes to synthesize CF3-containing aza-heterocycles

A light-induced, BiOBr nanosheets accelerated intermolecular one-pot tandem trifluoromethylation/arylation of alkenes was presented. With this method, a series of CF3-containing aza-heterocycles with high selectivity were fabricated in moderate to good yields. Preliminary mechanistic studies revealed that the exceptional transformation was originated from the synergistic effect of photogenerated electrons and holes. Density function theory (DFT) was adopted to understand the high selectivity of this photocatalytic chemical transformation.

The carbomethylation of arylacrylamides leading to 3-ethyl-3-substituted indolin-2-one by cascade radical addition/cyclization

An FeCl2-promoted carbomethylation of arylacrylamides by di-tert-butyl peroxide (DTBP) is achieved, leading to 3-ethyl-3-substituted indolin-2-one in high yield. The reaction tolerates a series of functional groups, such as cyano, nitro, ethyloxy carbonyl, bromo, chloro, and trifluoromethyl groups. The radical methylation and arylation of the alkenyl group are involved in this reaction. This journal is the Partner Organisations 2014.

Iron-catalyzed aerobic difunctionalization of alkenes: A highly efficient approach to construct oxindoles by C-S and C-C bond formation

A novel iron-catalyzed efficient approach to construct sulfone-containing oxindoles, which play important roles in the structural library design and drug discovery, has been developed. The use of readily available benzenesulfinic acids, an inexpensive iron salt as the catalyst, and air as the oxidant makes this sulfur incorporation protocol very efficient and practical. This journal is the Partner Organisations 2014.

Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides

Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright

Catalyst-free direct arylsulfonylation of N-arylacrylamides with sulfinic acids: A convenient and efficient route to sulfonated oxindoles

A simple, efficient and catalyst-free procedure has been developed for the construction of sulfonated oxindoles via the direct arylsulfonylation of N-arylacrylamides with sulfinic acids. The present protocol, which simply utilizes cheap oxidants, readily-available starting materials, and catalyst-free conditions, provides an alternative and highly attractive approach to a series of sulfonated oxindoles with high atom efficiency and excellent functional group tolerance. This journal is the Partner Organisations 2014.