111875-47-9

Upstream product

• 88070-48-8 N-methylbenzamide 
• 920-46-7 Methacryloyl chloride 
• 98-88-4 benzoyl chloride 
• 111875-30-0 N-benzoylformyl-N-methylmethacrylamide 

Relevant academic research and scientific papers

Photocatalytic C-C Bond Activation of Oxime Ester for Acyl Radical Generation and Application

A unified strategy to generate acyl radical from oxime ester via selective C-C bond activation is reported. Under visible-light irradiation, single-electron transfer from fac-Ir(ppy)3 to related oxime takes place followed by a fast β-fragment of C-C bond to yield aryl and aliphatic acyl radicals, subsequently captured by diverse Michael acceptors. More interestingly, the single-electron transfer enables coupling with energy transfer of the excited fac-Ir(ppy)3 via enone intermediate formed in situ for cyclobutane formation.

Visible-light-promoted acyl radical cascade reaction for accessing acylated isoquinoline-1,3(2: H,4 H)-dione derivatives

A visible-light-promoted decarboxylative acyl radical acylation/cyclization cascade reaction of N-methacryloylbenzamides for accessing acylated isoquinoline-1,3(2H,4H)-dione derivatives was described. In this report, α-keto acids were used for generating acyl radicals and inducing radical acylations. This protocol features mild reaction conditions, operational practicality and a broad substrate scope.

Metal-free visible-light-promoted thiocyanation/cyclization cascade for the synthesis of thiocyanato-containing isoquinolinediones

A visible-light induced metal-free thiocyanate radical addition/intramolecular cyclization cascade reaction for the synthesis of thiocyanato-containing isoquinolinediones from N-alkyl-N-methacryloylbenzamides is described. The organic dye 9-mesityl-10-methylacridinium perchlorate (Acr+-Mes ClO4 ?)is used as a photocatalyst, and cheap and readily available ammonium thiocyanate is used to provide thiocyanate radical by single-electron transfer pathway. The reaction completes the synthesis of C[sbnd]S and C[sbnd]C bonds in one pot with abundant molecular oxygen as the sole sacrificial reagent. The method is easy to implement, and 25 new compounds have been prepared in moderate to good yields under mild conditions. This is the first time that a thiocyanate group has been introduced into isoquinoline-1,3(2H,4H)-diones to construct highly functional drug-like molecules.

Aerobic thiyl radical addition/cyclization of N-methacryloyl benzamides for the synthesis of isoquinoline-1,3(2H,4H)-dione derivatives

A highly effective oxidative thiyl radical addition/cyclization of N-methacryloylbenzamides was explored using dioxygen as the sole terminal oxidant without the use of precious and/or toxic transition-metal catalysts. This method provides convenient access to a variety of useful sulfide-containing 4,4-disubstituted isoquinoline-1,3-diones by constructing C-S and C-C bonds in one step.

Radical-mediated divergent cyclization of benzamides toward perfluorinated or cyanated isoquinolinediones

A simple and efficient copper-controlled divergent cyclization of benzamides, which leads to perfluorinated or cyanated isoquinolinediones, is developed. In the presence of AIBN, methacryloyl benzamides with perfluoroalkyl iodides undergo cascade radical addition/cyclization to afford perfluoroinated isoquinolinediones as the major product under metal-free conditions, whereas the use of CuI (10 mol%) is able to redirect the cyclization to yield isoquinolinediones bearing an α-cyano quaternary carbon center. The cyclization features controllable divergent synthesis and a broad substrate scope as well as highly practical reaction conditions, thereby making this strategy a highly attractive means to fluorinate or cyanate isoquinolinediones.

Photochemical Reactions of N-Benzoylformyl α,β-Unsaturated Amides

N-Benzoylformyl α,β-unsaturated amides (1) underwent intramolecular cycloaddition to produce bicyclic imides, 1-phenyl-6-oxa-3-azabicyclopentane-2,4-diones (2), in good yield.Quantum yields for reaction of N-benzyl, N-(p-tolyl), and N-(2,6-xylyl)-N-benzoylformylmethacrylamide were 0.56, 0.04, and 0.10, respectively.