35690-67-6

Usage

Uses

Used in Pharmaceutical Industry:
1(2H)-Isoquinolinone, 3,4-dihydro-3-methylis used as a building block for the synthesis of various drugs and compounds. Its chemical structure and properties make it a versatile component in the development of new pharmaceuticals.
Used in Research and Development:
1(2H)-Isoquinolinone, 3,4-dihydro-3-methylis used as a subject of study in research for its potential biological activities and pharmacological properties. The investigation into its anti-inflammatory and analgesic effects contributes to the understanding of its therapeutic potential and safety profile, which is crucial for further development and application in the medical field.

Upstream product

• 103205-14-7 2-methylindanone oxime 
• 187737-37-7 propene 
• 61650-22-4 N-(pivaloyloxy)benzamide 
• 17496-14-9 2,3-dihydro-2-methyl-1H-inden-1-one 
• 70079-43-5 2-methyl-3-phenylpropionohydroxamic acid 

Downstream Products

• 848185-12-6 7-bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline 
• 6772-65-2 2-methyl-3,4-dihydro-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products

Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.

Rhodium(III)-Catalyzed C-H Activation: Ligand-Controlled Regioselective Synthesis of 4-Methyl-Substituted Dihydroisoquinolones

Rh-catalyzed C-H functionalization of O-pivaloyl benzhydroxamic acids with propene gas provides access to 4-methyl-substituted dihydroisoquinolones. Good to excellent levels of regioselectivity are achieved using [CptRhCl2]2 as a precatalyst under optimized conditions. Thorough examination of aryl/heteroaryl O-pivaloyl hydroxamic acid substrates, ligand effects on C-H site selectivity, alkene scope, and demonstration of scale are discussed within.

INTRAMOLECULAR AMIDATION OF ARYLALKYLHYDROXAMIC ACIDS

It is shown that mixtures of two isomeric benzolactams, viz., compounds of the benzamide and anilide type, are formed in the intramolecular amidation of arylalkylhydroxamic acids under the influence of polyphosphoric acid (PPA).A general reaction scheme that includes three pathways, viz., direct amidation, Losen rearrangement of the hydroxamic acids with subsequent cyclization of the isocyanates, and Beckmann rearrangement of the oximes of the cyclic ketones formed in the thermal cleavage of the starting hydroxamic acids in PPA, is proposed on the basis of a study of racemic and optically active arylalkylhydroxamic acids.