53854-49-2

Upstream product

• 119-65-3 isoquinoline 
• 75-03-6 ethyl iodide 

Downstream Products

• 20863-88-1 2-ethyl-1,3,4(2H)-isoquinolinetrione 

Relevant academic research and scientific papers

Reactions of isoquinoline derivatives with pyridinium salts yielding 4-naphthylpyridines

Regiospecific introduction of the 2-naphthyl residue into position 4 of the pyridine ring occurs in the reactions of isoquinolinium salts with 4-methylpyridinium salts through the intermolecular transformation of the isoquinoline bicyclic system involving the methyl group of the pyridinium salt. The reaction occurs under the action of methylammonium sulfite in an aqueous medium on heating. This method provides ring transformation not only for isoquinolinium salts but even for unsubstituted isoquinoline.

Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts

The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.

Synthesis of 4-Iodoisoquinolin-1(2 H)-ones by a Dirhodium(II)-Catalyzed 1,4-Bisfunctionalization of Isoquinolinium Iodide Salts

An efficient Rh2(II,II)-catalyzed reaction has been developed under mild conditions. This synthetic method proceeds through iodination/oxidation of readily available isoquinolinium iodide salts under aerobic conditions with good to excellent yields. 4-Iodoisoquinolin-1(2H)-ones are important building blocks for biologically and medicinally important compounds. The developed methodology was applied to the gram-scale synthesis of a key intermediate in the synthesis of the CRTH2 antagonist CRA-680.

Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.

One-Pot synthesis of coumarin-based oxazabicyclic and oxazatricyclic compounds and their fluorescence redox switching properties

An oxazabicycle and an oxazatricycle were efficiently synthesized by coupling of coumarins and N-alkylquinolium or isoquinolium salt to investigate their fluorescence redox-switchlng properties. Chemical reduction of the strongly fluorescent oxazabicycle