7115-13-1

Upstream product

• 23994-23-2 3-phenyl-isoquinoline-1,4-dione 
• 4809-08-9 3-phenyl-isocoumarin 
• 245122-81-0 1-ethoxy-3-phenylisoquinoline 
• 55150-54-4 1-chloro-3-phenylisoquinoline 
• 98-80-6 phenylboronic acid 
• 80221-08-5 2-(2-phenylethynyl)benzamide 
• 69909-00-8 α-Phenyl-zimtsaeureazid 
• 6639-19-6 N,N,2-trimethylbenzamide 
• 100-47-0 benzonitrile 
• 2728-04-3 N,N-diethyl-ortho-toluamide 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 3930-83-4 o-iodobenzamide 
• 98-86-2 acetophenone 
• 89641-06-5 2-iodo benzoyl azide 

Downstream Products

• 55150-55-5 1,4-dichloro-3-phenyl-isoquinoline 
• 55150-54-4 1-chloro-3-phenylisoquinoline 
• 181371-82-4 4-Nitro-3-phenyl-2H-isoquinolin-1-one 
• 180197-34-6 2-methyl-1-oxo-3-phenyl-1,2-dihydro-isoquinoline-4-carbaldehyde 
• 1352287-29-6 4-hydroxymethyl-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-44-5 4-methoxymethyl-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-47-8 4-ethoxymethyl-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-50-3 2-methyl-3-phenyl-4-propoxymethyl-2H-isoquinolin-1-one 
• 1352287-51-4 4-isopropoxymethyl-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-54-7 4-isobutoxymethyl-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-57-0 4-(2-hydroxy-ethoxymethyl)-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-60-5 4-(2-methoxy-ethoxymethyl)-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-63-8 4-(2-chloro-ethoxymethyl)-2-methyl-3-phenyl-2H-isoquinolin-1-one 
• 1352287-86-5 2-methyl-4-phenoxymethyl-3-phenyl-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

One-pot synthesis of 3-substituted isoquinolin-1-(2H)-ones and fused isoquinolin-1-(2H)-ones by SRN1 reactions in DMSO

3-Substituted isoquinolin-1-(2H)-ones and fused isoquinolin-1-(2H)-ones have been obtained by the photostimulated SRN1 reactions of 2-iodobenzamide with the enolates of aromatic (acetophenone, 1-(benzo[d][1,3]dioxol-5-yl)ethanone, 1- and 2-naph

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

C2-substituted quinazolinone derivatives exhibit A1 and/or A2A adenosine receptor affinities in the low micromolar range

Antagonists of the adenosine receptors (A1 and A2A subtypes) are widely researched as potential drug candidates for their role in Parkinson's disease-related cognitive deficits (A1 subtype), motor dysfunction (A2A subtype) and to exhibit neuroprotective properties (A2A subtype). Previously the benzo-α-pyrone based derivative, 3-phenyl-1H-2-benzopyran-1-one, was found to display both A1 and A2A adenosine receptor affinity in the low micromolar range. Prompted by this, the α-pyrone core was structurally modified to explore related benzoxazinone and quinazolinone homologues previously unknown as adenosine receptor antagonists. Overall, the C2-substituted quinazolinone analogues displayed superior A1 and A2A adenosine receptor affinity over their C2-substituted benzoxazinone homologues. The benzoxazinones were devoid of A2A adenosine receptor binding, with only two compounds displaying A1 adenosine receptor affinity. In turn, the quinazolinones displayed varying degrees of affinity (low micromolar range) towards the A1 and A2A adenosine receptor subtypes. The highest A1 adenosine receptor affinity and selectivity were favoured by methyl para-substitution of phenyl ring B (A1Ki = 2.50 μM). On the other hand, 3,4-dimethoxy substitution of phenyl ring B afforded the best A2A adenosine receptor binding (A2AKi = 2.81 μM) among the quinazolinones investigated. In conclusion, the quinazolinones are ideal lead compounds for further structural optimization to gain improved adenosine receptor affinity, which may find therapeutic relevance in Parkinson's disease-associated cognitive deficits and motor dysfunctions as well as exerting neuroprotective properties.

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.

Synthesis and Application of Heterocyclic Germatranes via Rhodium-Catalyzed Directed C?H Activation/Annulation with Alkynyl Germatranes and Palladium-Catalyzed Cross-Coupling

Rhodium-catalyzed C?H activation and annulation with alkynyl germatranes for the synthesis of heterocyclic germatranes is described. Various heterocyclic germatranes were constructed by this protocol and applied in multiple derivatizations such as palladi

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.

Ruthenium(II)-Catalyzed Homocoupling of Weakly Coordinating Sulfoxonium Ylides via C?H Activation/Annulations: Synthesis of Functionalized Isocoumarins

Homocoupling of weakly coordinating sulfoxonium ylides was accomplished via ruthenium (II) catalyzed C?H activation process. This strategy provides a convenient, efficient and step-economic method to access 3-substituted isocoumarins with good functional

Tunable Synthesis of 3-Hydroxylisoquinolin-1,4-dione and Isoquinolin-1-one Enabled by Copper-Catalyzed Radical 6- endo Aza-cyclization of 2-Alkynylbenzamide

In this work, switchable synthesis of isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione from 2-alkynylbenzamide is reported. The transformation works well with good yields and a broad reaction scope. The synthetic switch for providing isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione is enabled by the use of a N2 or O2 atmosphere. Mechanism studies show that the reaction proceeds in a regioselective manner via a N-center radical 6-endo-dig aza-cyclization pathway.

Palladium-Catalyzed Inert C?H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1-b]isoquinoline-5,7-Diones

A palladium-catalyzed inert C?H bond activation and cyclocarbonylation of isoquinolones leading to isoindolo[2,1-b]isoquinoline-5,7-diones under 1 atm of carbon dioxide has been developed. This transformation features high regio- and chemo-selectivity, step-economy, and good functional group tolerance. Most of the corresponding products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse isoindolo[2,1-b]isoquinoline-5,7-dione derivatives. (Figure presented.).

Electroremovable Traceless Hydrazides for Cobalt-Catalyzed Electro-Oxidative C-H/N-H Activation with Internal Alkynes

Electrochemical oxidative C-H/N-H activations have been accomplished with a versatile cobalt catalyst in terms of [4 + 2] annulations of internal alkynes. The electro-oxidative C-H activation manifold proved viable with an undivided cell setup under exceedingly mild reaction conditions at room temperature using earth-abundant cobalt catalysts. The electrochemical cobalt catalysis prevents the use of transition metal oxidants in C-H activation catalysis, generating H2 as the sole byproduct. Detailed mechanistic studies provided strong support for a facile C-H cobaltation by an initially formed cobalt(III) catalyst. The subsequent alkyne migratory insertion was interrogated by mass spectrometry and DFT calculations, providing strong support for a facile C-H activation and the formation of a key seven-membered cobalta(III) cycle in a regioselective fashion. Key to success for the unprecedented use of internal alkynes in electrochemical C-H/N-H activations was represented by the use of N-2-pyridylhydrazides, for which we developed a traceless electrocleavage strategy by electroreductive samarium catalysis at room temperature.