Synthesis of Imidazo[2,1- a ]isoindolones via Rearrangement and Tandem Cyclization of Amino-Acid-Based N -Phenacyl-2-cyano-4-nitrobenzensulfonamides
Year: 2025
Type: article
Abstract: Esters of amino acids were reacted with 2-cyano-4-nitrobenzenesulfonyl chloride or 2-cyano-4-(trifluoromethyl)benzenesulfonyl chloride and alkylated with various α-haloketones. The corresponding sulfonamides were heated in a solution of ammonium acetate, which yielded imidazo[2,1-a]isoindolones in one step. The key reaction was based on intramolecular C-arylation followed by spontaneous cycloaddition and cyclocondensation. Two approaches have been developed: (i) solid-phase synthesis starting from amino acids immobilized on Wang resin, which allows the rapid preparation of target compounds using the cyclative cleavage strategy, and (ii) traditional solution-phase synthesis using amino acid methyl esters as the starting materials. The advantages and drawbacks of both alternatives are compared.
Source: The Journal of Organic Chemistry
Institution: Palacký University Olomouc
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W4410764607