138037-41-9

Usage

Structure

Substituted quinolinone derivative with an iodine atom and a methyl group

Physical form

Yellow crystalline solid

Solubility

Insoluble in water

Use

Building block in organic synthesis, reagent in chemical reactions

Potential applications

Pharmaceuticals and agrochemicals due to versatile reactivity and structural properties.

Upstream product

• 3947-76-0 N-methylquinolinium iodide 
• 5471-63-6 1,3-diphenylisobenzofuran 
• 79476-07-6 3-Iodoquinoline 
• 91-22-5 quinoline 
• 606-43-9 1-methyl-2-quinolin-2(1H)-one 

Downstream Products

• 251089-11-9 1-methyl-3-(o-nitrophenyl)-1H-quinoline-2-one 
• 138037-42-0 3,6-Diphenyl-1-methylquinolinone 

Relevant academic research and scientific papers

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.

The regioselective iodination of quinolines, quinolones, pyridones, pyridines and uracil

A radical based direct C-H iodination protocol for quinolines, quinolones, pyridones, pyridines, and uracil has been developed. The iodination occurs in a C3 selective manner for quinolines and quinolones. Pyridones and pyridines undergo C3 and C5 iodination, while dimethyl uracil undergoes C5 iodination. Scope of the method was demonstrated through the rapid synthesis of both electron rich as well as electron poor heteroaromatic iodides. The protocol was found to be scalable and general, while a mechanism has been proposed.