72601-46-8

Usage

Chemical compound

2,5-Pyrrolidinedione, 1-(3-iodophenyl)-

Physical properties

white to yellow crystalline powder

Uses

commonly used in pharmaceutical research and development

Structure

derivative of pyrrolidinedione with a 3-iodophenyl substituent at the 1-position

Reactivity

utilized as an intermediate in the synthesis of various pharmaceuticals and bioactive compounds

Medicinal properties

studied for its potential as an anti-inflammatory and analgesic agent

Handling

important to handle with caution as it is hazardous if not properly managed

Upstream product

• 108-30-5 succinic acid anhydride 
• 626-01-7 3-Iodoaniline 
• 123-56-8 Succinimide 
• 221037-98-5 (3-iodophenyl)boronic acid 

Downstream Products

• 1172604-96-4 (E)-N-(3-(3-(2,5-dioxopyrrolidin-1-yl)phenyl)prop-2-enyl)-2-iodo-3-nitrobenzamide 
• 1172604-97-5 N-(2-(3-(2,5-dioxopyrrolidin-1-yl)phenyl)prop-2-enyl)-2-iodo-3-nitrobenzamide 
• 1172604-92-0 (E)-1,1-dimethylethyl N-(3-(3-(2,5-dioxopyrrolidin-1-yl)phenyl)prop-2-enyl)carbamate 
• 1172604-93-1 1,1-dimethylethyl N-(2-(3-(2,5-dioxopyrrolidin-1-yl)phenyl)prop-2-enyl)carbamate 
• 1172604-94-2 C₁₃H₁₄N₂O₂ 
• 1172604-95-3 C₁₃H₁₄N₂O₂ 

Relevant academic research and scientific papers

4-Substituted 5-nitroisoquinolin-1-ones from intramolecular Pd-catalysed reaction of N-(2-alkenyl)-2-halo-3-nitrobenzamides

4-Methyl- and 4-benzyl-5-aminoisoquinolin-1-ones are close analogues of the water-soluble PARP-1 inhibitor 5-AIQ. Their synthesis was approached through Pd-catalysed cyclisations of N-(2-alkenyl)-2-iodo-3-nitrobenzamides. Reaction of N,N-diallyl-2-iodo-3-nitrobenzamide with Pd(PPh3)4 gave a mixture of 2-allyl-4-methyl-5-nitroisoquinolin-1-one and 2-allyl-4-methylene-5-nitro-3,4-dihydroisoquinolin-1-one. N-Benzhydryl-N-cinnamyl-2-iodo-3-nitrobenzamide similarly gave 2-benzhydryl-4-benzyl-5-nitroisoquinolin-1-one and 2-benzhydryl-4-benzylidene-5-nitro-3,4-dihydroisoquinolin-1-one. The isomeric products are not interconvertible. A deuterium-labelling study indicated that the isomers were formed by different pathways: a π-allyl-Pd route and the classical Heck route. The corresponding secondary amides N-allyl-2-iodo-3-nitrobenzamide and N-((substituted)-cinnamyl)-2-iodo-3-nitrobenzamide gave good yields of the required 4-methyl- and 4-((substituted)-benzyl)-5-nitroisoquinolin-1-ones, respectively, under optimised conditions (Pd(PPh3)4, Et3N, Bu4NCl, 150 °C, rapid heating). Hydrogenation of the nitro groups gave 4-methyl- and 4-benzyl-5-aminoisoquinolin-1-ones, which were potent inhibitors of PARP-1 activity.

Comparison of copper(II) acetate promoted N-arylation of 5,5-dimethyl hydantoin and other imides with triarylbismuthanes and aryl boronic acids

This work demonstrates that the copper acetate promoted N-arylation of imides with boronic acids can be employed as a major method for the synthesis of N3-aryl hydantoins. Georg Thieme Verlag Stuttgart.