Title: 2-Substituted-isoindoles: a novel synthetic route and a study of the Diels-Alder and Michael reactions.
Authors: Voitenko, Zoia V.; Sypchenko, Volodymyr V.; Levkov, Igor V.; Potikha, Lyudmila M.; Kovtunenko, Volodymyr A.; Shishkin, Oleg V.; Shishkina, Svetlana V.
Abstract: A novel one-step procedure for the synthesis of 2-substituted-isoindoles and 1-aryl-2-substituted-isoindoles is described. The procedure is based on the reaction of 2-(bromomethyl)benzaldehyde or 2-(bromomethyl)benzophenone derivatives with primary aromatic or aliphatic amines. Reactions of 1,2-diarylisoindoles with N-phenylmaleimide were studied. Refluxing the reactants in i-PrOH in the presence of triethylamine leads to the formation of Diels-Alder endo-adducts; whilst refluxing in AcOH in the presence of AcONa affords Michael adducts. The structure of the latter was confirmed by X-ray diffraction.
Subjects: CHEMICALS; CHEMICAL synthesis; ISOINDOLE; BENZALDEHYDE; BENZOPHENONES; ALIPHATIC amines; X-ray diffraction
Publication: Journal of Chemical Research, 2011, Vol 35, Issue 11, p615
ISSN: 1747-5198
Publication type: Academic Journal
DOI: 10.3184/174751911X13179842027190

2-Substituted-isoindoles: a novel synthetic route and a study of the Diels-Alder and Michael reactions.

Voitenko, Zoia V.; Sypchenko, Volodymyr V.; Levkov, Igor V.; Potikha, Lyudmila M.; Kovtunenko, Volodymyr A.; Shishkin, Oleg V.; Shishkina, Svetlana V.