Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 24, Pages 6988-6991Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602288
Keywords
[2+4] reactions; aza-o-xylylenes; dearomatization; photochemistry; polyheterocycles
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Funding
- NIH [GM093930]
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A new method was developed for the photoinduced dearomatization of arenes through an intramolecular cycloaddition with aza-o-xylylenes generated by excited-state intramolecular proton transfer (ESIPT) in the readily available photoprecursors. The [2+4] topology of this cycloaddition is unprecedented for photo-dearomatizations of benzenoid aromatic carbocycles. It provides rapid access to novel heterocycles, cyclohexadieno-oxazolidino-quinolinols, as valuable synthons for a broad range of post-photochemical transformations.
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