Synthesis of Substituted Phthalimides via Ultrasound-Promoted One-Pot Multicomponent Reaction

In this work, a novel strategy for the straightforward synthesis of substituted phthalimides is described, which includes base-mediated Michael addition/intramolecular cyclization/[1,5]-H shift/cleavage of CS2/aromatization/nucleophilic acyl substitution reaction of 2-(4-oxo-2-thioxothiazolidin-5-yl...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-01, Vol.86 (1), p.574-580
Main Authors: Alizadeh, Abdolali, Farajpour, Behnaz, Knedel, Tim-Oliver, Janiak, Christoph
Format: Article
Language:English
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Summary:In this work, a novel strategy for the straightforward synthesis of substituted phthalimides is described, which includes base-mediated Michael addition/intramolecular cyclization/[1,5]-H shift/cleavage of CS2/aromatization/nucleophilic acyl substitution reaction of 2-(4-oxo-2-thioxothiazolidin-5-ylidene)­acetates and α,α-dicyanoolefines under ultrasound (US) irradiation. Some advantages of this method are as follows: having simple operation, easily accessible starting materials, chemoselective cascade process, synthetically useful yields, and green conditions by utilizing US irradiation as a source of energy and using ethanol as solvent.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02245