13670-91-2

Upstream product

• 3930-83-4 o-iodobenzamide 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 4001-73-4 2-Bromobenzamide 
• 874-90-8 4-methoxybenzonitrile 
• 2170-09-4 N,2-dimethylbenzamide 
• 100-66-3 methoxybenzene 
• 25407-08-3 2-((4-methoxyphenyl)ethynyl)benzamide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 5597-04-6 2-cyanomethylbenzoic acid methyl ester 
• 130818-20-1 2-(2-(4-methoxyphenyl)ethynyl)benzoic acid methyl ester 
• 768-60-5 4-methoxyphenylacetylen 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 2728-04-3 N,N-diethyl-ortho-toluamide 
• 4387-36-4 2-iodobenzonitrile 

Downstream Products

• 20434-92-8 3-(4-hydroxyphenyl)-2H-isoquinolin-1-one 
• 20435-80-7 1,4-dichloro-3-(4-methoxy-phenyl)-isoquinoline 
• 181371-92-6 [3-(4-Methoxy-phenyl)-1-oxo-1,2-dihydro-isoquinolin-4-yl]-carbamic acid ethyl ester 
• 181372-16-7 N-[3-(4-Methoxy-phenyl)-1-oxo-1,2-dihydro-isoquinolin-4-yl]-acetamide 

Relevant academic research and scientific papers

Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones

A striking dependence on the method of workup has been found for annulation of benzonitriles ArCN to N-methyl 2-toluamide (1), facilitated by n-BuLi (2 equiv): Quenching the reaction by a slow addition of water produced the expected 1-isoquinolones 2; by

Base-Mediated Anti-Markovnikov Hydroamidation of Vinyl Arenes with Arylamides

We investigated a base-promoted protocol for the intermolecular anti-Markovnikov hydroamidation of vinyl arenes with arylamides to furnish the arylethylbenzamides with excellent chemo- and regioselectivity. The reaction tolerates an extensive variety of functional groups and has been successfully extended with electronically varied handles, aminobenzamides, electron-rich/electron-deficient heterocyclic amides, and vinyl arenes to afford the hydroamidated products. Excellent chemoselectivity was observed for the amide group over amine. The proposed mechanism and vital role of the solvent was well supported by deuterium labeling studies and control experiments.

Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate

A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Br?nsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Br?nsted acid induced intramolecular cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.

Nickel-Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2-MeTHF: Eco-Friendly Synthesis of Aminoisoquinolines and Isoquinolones

The first example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates with arylboronic acids. The use of the bio-based and green solvent 2-MeTHF as the reaction medium makes the synthesis process environmentally benign. The synthetic utility of this chemistry is also indicated by the synthesis of biologically active molecules.

Design, synthesis, and biological evaluation of 1,3-diarylisoquinolines as novel topoisomerase I catalytic inhibitors

With a goal of identifying potent topoisomerase (topo) inhibitor, the C4-aromatic ring of the anticancer agent, 3,4-diarylisoquinolone, was strategically shifted to design 1,3-diarylisoquinoline. Twenty-two target compounds were synthesized in three simple and efficient steps. The 1,3-diarylisoquinolines exhibited potent anti-proliferative effects on cancer cells but few compounds spared non-cancerous cells. Inhibition of topo I/IIα-mediated DNA relaxation by several derivatives was greater than that by camptothecin (CPT)/etoposide even at low concentration (20 μM). In addition, these compounds had little or no effect on polymerization of tubulin. A series of biological evaluations performed with the most potent derivative 4cc revealed that the compound is a non-intercalative topo I catalytic inhibitor interacting with free topo I. Collectively, the potent cytotoxic effect on cancer cells including the drug resistance ones, absence of lethal effect on normal cells, and different mechanism of action than topo I poisons suggest that the 1,3-diarylisoquinolines might be a promising class of anticancer agents worthy of further pursuit.

On-Water Silver(I)-Catalyzed Cycloisomerization of Acetylenic Free Amines/Amides towards 7-Azaindole/Indole/Isoquinolone Derivatives

Silver-catalyzed on-water intramolecular cyclization of acetylenic free amines is reported, which affords 7-azaindoles in good to excellent yields. Neither strong base/acid catalysts nor N-substituted substrates are required to achieve this cycloisomerization. Hydrogen bonds between water medium and the substrates play an important role in improving chemical reactivity and regioselectivity. Furthermore, the on-water reaction is extendable to acetylenic amides for isoquinolone synthesis.

Method of catalyzing tandem reaction to synthesize isoquinolinone derivative in water phase

The invention provides a method of catalyzing tandem reaction to synthesize isoquinolinone derivative in water phase. In the method, the isoquinolinone derivative is synthesized in a one-pot manner that on the basis of 1 mol of 0.1-1 mol/L ortho-halogenated benzamide and 0.1-5 mol of a terminal alkyne, a reaction is carried out in a water phase under the effect of 0.001-1 mol of bivalent copper salt and phenanthroline catalysts in the presence of 0.5-6 mol of inorganic alkali or organic alkali, reaction temperature being 20-160 DEG C and reaction time being 1-50 h. In the method, the bivalent copper salt and phenanthroline can catalyze the reaction between the ortho-halogenated benzamide and the terminal alkyne in the water phase, wherein water serves as a solvent, so that the method is environment-friendly, and avoids usage of noble metals, high temperature reaction and the like reaction conditions. The method has simple operations and high yield, is safe and low-cost, is low in pollution and is suitable for various functional groups.

Novel Diarylisoquinolines and Pharmaceutical Composition Comprising the Same

The present invention relates to novel diarylisoquinolone or diarylisoquinoline compounds. The compounds of the present invention show selective cytotoxicity in human ductal carcinoma cell line (T47D), human prostate cancer cell line (DU145), and human co

Tandem addition/cyclization for access to isoquinolines and isoquinolones via catalytic carbopalladation of nitriles

The first example of the palladium-catalyzed sequential nucleophilic addition followed by an intramolecular cyclization of functionalized nitriles with arylboronic acids has been achieved, providing an efficient synthetic pathway to access structurally di

A different quinolinone and its derivatives

The invention belongs to the technical field of pharmaceutical and chemical intermediates and related chemicals and relates to a preparation method of isoquinolone and derivatives thereof. The isoquinolone and derivatives thereof are important biologically active molecules, skeletal structures frequently appear in natural molecules and drug molecules, and have better therapeutic effect on hypertension, cancer and anxiety disorders and important applications in the fields of organic synthesis and pharmaceutical chemistry. The method is short in synthesis route, mild in conditions and simple in operation and is expected to achieve industrial production and has the advantages of short synthetic route, mild conditions, simple operation and high yield and the like. The isoquinolone and derivatives thereof have greater application value and social and economic benefits.