131002-10-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Methylisoquinolin-1(2H)-one is used as a key intermediate in the synthesis of substituted isoquinolones, which are important for the development of various pharmaceuticals. These substituted isoquinolones can exhibit a range of biological activities, such as anti-inflammatory, analgesic, and antipyretic properties, making them valuable in the treatment of various medical conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 6-methylisoquinolin-1(2H)-one serves as a versatile building block for the preparation of a wide range of organic compounds. Its unique structure allows for various chemical reactions, such as alkylation, acylation, and amination, enabling the synthesis of diverse organic molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
6-Methylisoquinolin-1(2H)-one is also utilized in research and development settings for the study of isoquinoline chemistry and the exploration of new synthetic routes and methodologies. Its reactivity and structural features make it an attractive candidate for the development of novel synthetic strategies and the discovery of new compounds with potential applications in various fields.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1419, 1990 DOI: 10.1002/jhet.5570270544

Upstream product

• 70810-28-5 6-methylisoquinoline N-oxide 
• 42398-73-2 6-methylisoquinoline 
• 630422-65-0 3-meta-tolyl-acryloyl azide 
• 108-05-4 vinyl acetate 
• 25563-06-8 N-methoxy-4-methylbenzamide 
• 13162-05-5 n-vinylformamide 
• 99-94-5 p-Toluic acid 
• 1623775-07-4 N-{2-(1-benzyl-1H-1,2,3-triazol-4-yl)propan-2-yl}-4-methylbenzamide 
• 874-60-2 4-methyl-benzoyl chloride 
• 131002-03-4 4-methyl-2- bromobenzamide 
• 131002-07-8 2-ethenyl-4-methylbenzamide 

Downstream Products

• 209286-73-7 1-chloro-6-methylisoquinoline 
• 1351399-89-7 C₃₁H₂₈INO₅S 
• 300546-02-5 C₃₁H₂₉NO₆ 
• 444898-39-9 C₃₆H₂₉NO₈ 

Relevant academic research and scientific papers

Ruthenium(II)-Catalyzed C?H Activation/Annulation of Aromatic Hydroxamic Acid Esters with Enamides Leading to Aminal Motifs

Hydroxamic acid ester directed C(sp2)?H activation/annulation strategy has been reported employing electron-rich enamides under Ru(II)-catalysis to access aminal frameworks. Both N-vinyl acetamide and N-vinyl formamide delivered aminals bearing

Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides

Cyclobutanes are an important class of motifs present in a wide range of natural products and other biologically significant molecules. A photocatalytic [2 + 2] cycloaddition between pyridones or isoquinolones and ethenesulfonyl fluoride was achieved, providing a portal to a class of unique cyclobutane-fused pyridinyl sulfonyl fluorides with quaternary rigid rings (30 examples). Further applications of these novel sulfonyl fluoride molecules in SuFEx click chemistry were also accomplished, providing the corresponding sulfonates and sulphonamides with reasonable yields.

Aromatic compounds and preparation method and application thereof

The invention discloses aromatic compounds and a preparation method and application thereof. The preparation method of the aromatic compounds includes the step of performing a cyclization reaction between an amide compound and a benzoic acid compound in the presence of a rhodium catalyst, a metal oxidant and base, wherein the aromatic compounds are isoquinolinone compounds or isocoumarin derivatives, and the amide compound is N-vinylformamide or N-vinylacetamide. Through the synergistic effect of the rhodium catalyst, the metal oxidant and the base, the isoquinolinone compounds or isocoumarinderivatives are obtained through the one-step reaction between the benzoic acid compound and the amide compound. The reaction has simple operation, the raw materials are cheap and easily available, reaction substrates can be selected flexibly according to the required isoquinolinone compounds and the isocoumarin derivatives, and the synthesized isoquinolinone compounds and the isocoumarin derivatives can be used as a backbone structure in multiple biologically active molecules and natural products, and have high practicality.

Divergent Synthesis of Isoquinolone and Isocoumarin Derivatives by the Annulation of Benzoic Acid with N-Vinyl Amide

A simple and efficient method for the synthesis of isoquinolone and isocoumarin derivatives is reported. The method for the first time provides a one-step divergent synthesis of important isoquinolone and isocoumarin skeletons from benzoic acid by switching the coupling partners. In addition, a reliable mechanism has been proposed on the basis of experimental investigations, including kinetic isotope effect experiments, 13C labeling experiments, time-tracking experiments, and competitive experiments, as well as DFT calculation studies.

Iron-Catalyzed C?H Alkynylation through Triazole Assistance: Expedient Access to Bioactive Heterocycles

Triazole assistance enabled the first iron-catalyzed C?H alkynylation of arenes, heteroarenes, and alkenes. The modular TAM directing group set the stage for a sequential C?H alkynylation/annulation strategy with ample scope, enabling the iron-catalyzed assembly of isoquinolones, pyridones, pyrrolones, and isoindolinones with high levels of chemo-, site-, and regioselectivity.

Design, synthesis, and biological evaluation of pyrazinones containing novel P1 needles as inhibitors of TF/VIIa

Herein is described the design, synthesis, and enzymatic activity of a series of substituted pyrazinones as inhibitors of the TF/VIIa complex. These inhibitors were designed to explore replacement and variation of the P1 amidine described previously [J. Med. Chem. 2003, 46, 4050]. The P1 needle replacements were selected based upon their reduced basicity compared to the parent phenyl amidine (pKa ～ 12). A contributing factor towards the oral bioavailability of a compound is the ionization state of the compound in the intestinal tract. The desired outcome of the study was to identify an orally bioavailable TF-VIIa inhibitor.

HEPATITIS C VIRUS INHIBITORS

Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

Synthesis of novel substituted isoquinolones

A series of novel substituted isoquinolones have been synthesised. This has been achieved by two routes, either Curtius rearrangment of cinnamic acids or via an isoquinoline N-oxide.

Palladium-catalyzed Synthesis of Isocoumarin and 1-Isoquinolinone Derivatives

In the presence of copper(I) chloride, the palladium catalyzed oxidation of methyl 2-ethenylbenzoates and 2-ethenylbenzamides have been studied.This reaction was used to form isocoumarins and 1-isoquinolinones.