Journal
SYNLETT
Volume 31, Issue 3, Pages 255-260Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690782
Keywords
furan; Diels-Alder reaction; transposition of aromaticity; furo[2,3f]isoindole; IMDAV reaction; atom-efficient reaction
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Funding
- Russian Science Foundation (RSF) [18-13-00456]
- Russian Science Foundation [18-13-00456] Funding Source: Russian Science Foundation
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An unexpected four-step reaction sequence was discovered in the course of investigation of the interaction between 3-(furan-2-yl)allylamines and bromomaleic anhydride. This conversion begins with the initial N -acylation of the allylamines by the anhydride, followed by intramolecular Diels-Alder reaction, which is accompanied by a dehydrohalogenation, and ends with the formation of partially unsaturated furo[2,3- f ]isoindoles followed by transposition of aromaticity from the furan moiety to the neighboring cyclohexane ring. The reaction between 3-(furan-3-yl)allylamines and bromomaleic anhydride does not stop at a furo[2,3- f ]isoindole formation step, but proceeds further with the cleavage of the furan ring in a 100% atom-efficient fashion to provide polysubstituted isoindoline-4-carboxylic acids.
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