24188-76-9

Usage

Uses

Used in Pharmaceutical Industry:
[1,3]Dioxolo[4,5-g]isoquinolin-5(6H)-one is utilized as a key intermediate in the synthesis of biologically active compounds for the development of new therapeutic agents. Its unique structure and reactivity contribute to the creation of pharmaceuticals targeting a range of diseases, including cancer and infectious diseases.
Used in Organic Synthesis:
In the field of organic synthesis, [1,3]dioxolo[4,5-g]isoquinolin-5(6H)-one is employed as a versatile building block. Its synthetic utility allows for the construction of complex molecular architectures, facilitating the discovery and optimization of new chemical entities with potential applications in various therapeutic areas.
Used in Drug Discovery:
[1,3]Dioxolo[4,5-g]isoquinolin-5(6H)-one is leveraged in drug discovery as a valuable intermediate for the synthesis of compounds with potential medicinal properties. Its unique structural features and reactivity make it an attractive candidate for the development of new drugs, particularly those aimed at treating challenging diseases such as cancer and infectious diseases.

Upstream product

• 21796-14-5 noroxyhydrastinine 
• 62-31-7 dopamine hydrochloride 
• 36205-85-3 ethyl (3,4-dihydroxyphenethyl)carbamate 
• 82463-74-9 6-Bromo-1,3-benzodioxole-5-carboxamide 

Downstream Products

• 475-75-2 liriodenine 
• 1432725-89-7 (2-bromo-5-trifluoromethylphenyl)(6,7-methylenedioxyisoquinolin-1-yl)methanone 
• 1432725-87-5 (2-bromo-4,5-dimethoxyphenyl)(6,7-methylenedioxyisoquinolin-1-yl)methanone 
• 87489-85-8 (2-bromophenyl)([1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanone 
• 1432725-73-9 (2-bromo-5-trifluoromethylphenyl)(6,7-methylenedioxyisoquinolin-1-yl)acetonitrile 
• 1432725-71-7 (2-bromo-4,5-dimethoxyphenyl)(6,7-methylenedioxyisoquinolin-1-yl)acetonitrile 
• 1432725-70-6 (2-bromophenyl)(6,7-methylenedioxyisoquinolin-1-yl)acetonitrile 

Relevant academic research and scientific papers

A versatile approach to 1-oxo-, 1-oxo-3,4-dihydro- and 1,3,4-trioxo isoquinoline alkaloids and first total synthesis of the dimeric 1-oxoisoquinoline alkaloids berbanine and berbidine

We have worked out a very short approach to 1-oxoisoquinoline alkaloids starting from readily available 2-bromobenzamides utilizing a 2-ethoxyvinylboronate as a C2 building block for introduction of the C-3,C-4 unit of the isoquinoline core. TF

Photocycloaddition and Rearrangement Reactions in a Putative Route to the Skeleton of Plicamine-Type Alkaloids

Two isoquinolones were prepared, to which an allenyl side chain was linked at position C4 via a stereogenic silyloxy-substituted carbon atom. Intramolecular [2+2] photocycloaddition reactions of these substrates proceeded with high diastereoselectivity and delivered the respective cyclobutanes with an exocyclic methylene group (83% and 49% yield). With the 5,6-dioxoloisoquinolone precursor an unprecedented meta-photocycloaddition was observed as a significant side reaction, which occurred at positions C4 and C8a of the isoquinolone skeleton. The cyclobutane products were, after N-alkylation and transformation into the respective cyclobutanones (22-57%), subjected to various rearrangement reactions. In detail, a direct photochemical rearrangement, thermal and photochemical Beckmann rearrangements, and Baeyer-Villiger oxidation reactions were studied. In all cases, products were found, which resulted from cleavage of the amino-substituted cyclobutane bond, but not from the desired cleavage of the alternative alkyl-substituted cyclobutane bond.