64840-53-5

Upstream product

• 52166-52-6 2-benzyl-5-nitroisoquinolinium 
• 77747-69-4 5-nitro-1H-isochromen-1-one 
• 100-46-9 benzylamine 
• 607-32-9 5-nitroisoquinoline 
• 108-88-3 toluene 
• 100-39-0 benzyl bromide 
• 57249-08-8 N-benzyl-5-nitroisoquinolin-2-ium bromide 

Downstream Products

• 757966-62-4 5-Amino-2-benzyl-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

Iodine-Catalyzed Oxidative Functionalization of Azaarenes with Benzylic C(sp3)-H Bonds via N-Alkylation/Amidation Cascade: Two-Step Synthesis of Isoindolo[2,1-b]isoquinolin-7(5H)-one

An efficient and practical iodine-catalyzed oxidative functionalization of azaarenes with benzylic C-H bonds via an N-alkylation and amidation cascade is developed to provide isoquinolin-1(2H)-ones. This method utilizes readily available unfunctionalized azaarenes and methylarenes as starting materials and proceeds under metal-free conditions with good to excellent yields, avoiding the use of expensive noble metal catalysts and generation of halide and metal wastes. The synthetic utility of this reaction is exemplified by the concise, two-step synthesis of isoindolo[2,1-b]isoquinolin-7(5H)-one.

Light-driven selective aerobic oxidation of (iso)quinoliniums and related heterocycles

Selective C1-H/C4-H carbonylation of N-methylene iminium salts, catalyzed by visible-light photoredox and oxygen in the air, has been reported. A ruthenium complex acts as a chemical switch to conduct two different reaction pathways and to afford two diff

Base-promoted aerobic oxidation of: N -alkyl iminium salts derived from isoquinolines and related heterocycles

Potassium tert-butoxide-promoted aerobic oxidation of N-alkyl iminium salts is reported. The reaction is atom-economical and environmentally friendly. Iminium salts derived from isoquinoline, quinoline, phenanthridine, phenanthroline, and phthalazine were successfully transformed into their corresponding unsaturated lactams with up to 95% yield under mild conditions in the absence of photocatalysts and metallic or organic catalysts. Owing to the general substrate scope, low cost, feasibility of scale up, wide availability of reagents, and green reaction conditions, this method shows great potential for preparing isoquinolones and related compounds. The method was applied for atom- and step-economical total synthesis of natural products such as norketoyobyrine.

Substituted tetrahydroisoquinolines and uses thereof

The invention provides compounds of the formula: and pharmaceutically acceptable salts or prodrugs thereof, wherein, n, X, Y, R1, R2, R3, R4 and R5 are as defined herein. The invention also provides methods for preparing, compositions comprising, and methods for using compounds of formula I.

Kinetics of the Oxidation of Isoquinolinium Cations by Ferricyanide Ion

The rates of the ferricyanide oxidation of a number of isoquinolinium cations have been investigated in the range pH 11-14 in 20percent CH3CN-80percent H2O at 25 deg C (ionic strength 1.0).The oxidation of the 2-methylisoquinolinium cation is kinetically first order in each of ferricyanide ion and isoquinolinium cation but is subject to pronounced inhibition by the ferrocyanide ion reaction product.Second-order rate constants evaluated from initial reaction rates display a pH dependence which is consistent with rate-determining ferricyanide attack on the pseudobase alkoxide ion derived from the isoquinolinium cation.Ferrocyanide ion inhibition is shown to be consistent with this initial electron transfer being a reversible process.Similar observations are made for a number of substituted isoquinolinium cations.Substituent effects are shown to be consistent with electron abstraction from the endocyclic nitrogen atom rather than the exocyclic oxyanion of these pseudobase alkoxide ions.The initially formed radical then undergoes a base-catalyzed deprotonation from C-1, and this is confirmed by deuterium kinetic isotope effects when a deuterium label is present at C-1.The combination of these pH effects leads to ferrocyanide ion inhibition becoming less pronounced with increasing pH.These observations have prompted us to reinvestigate the ferricyanide ion oxidation of some of the 5-nitroisoquinolinium cations that we have previously studied.We find that ferrocyanide ion inhibition is observable when the initial rates of these reactions are examined in the stopped-flow spectrophotometer.Detailed kinetic analysis of these oxidations is shown to be consistent with the reaction scheme detailed above for the 2-methylisoquinolinium cation.In the light of this work, we must now withdraw our earlier claim for rate-determining hydride abstraction in these reactions.Substituent effects on the oxidation of these isoquinolinium cations allow the development of a relationship which can be used to predict the pH-rate profile for the ferricyanide ion oxidation of any isoquinolinium cation for which pKR+ for pseudobase formation is available, provided that steric hindrance from the N substituent is not significant.