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Paper | Regular issue | Vol 55, No. 9, 2001, pp.1663-1678
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9212
Synthesis of 3-Substituted Isoindolin-1-ones by Regioselective Cyclization of Nitrile with a Styryl Double Bond

Fen-Tair Luo* and Chin-Hsin Chen

*Institutue of Chemistry, Academia Sinica,, Nankang, Taipei,11529,Taiwan, R.O.C.


An efficient preparation of 3-substituted isoindolin-1-one was established via basic condensation of aromatic or aliphatic aldehyde with 6-alkoxy-3-methylbenzene-1,2,4-tricarbonitrile (1) in a one-pot reaction. The key step involved regioselective either hydrolysis or nucleophilic attack of the hydroxide anion to the 2-cyano group followed by 5-exo-trig cyclization with the involvement of the styryl double bond. The structure of isoindolinone and regiochemistry of the cyclization products were proved by spectroscopic methods.