Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 11-12, Pages 2609-2626Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201301105
Keywords
copper catalysts; fused isoquinolinones; iminoisoindolinones; regioselective switching
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Funding
- National Science Council of the Republic of China [NSC 100-2113M-003-008-MY3]
- National Taiwan Normal University [99T3030-2, 99-D, 100-D-06]
- Instrumentation Centre at National Taiwan Normal University
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Copper-catalyzed base switching procedures for the synthesis of various fused isoquinolinone derivatives and iminoisoindolinone derivatives from the same starting materials have been developed. In these reaction sequences it is found that benzyl cyanide acts as a nucleophile in the presence of strong bases while it acts as a cyanide donor in the presence of weak bases. A wide substrate scope, good functional group tolerance, and handy reaction conditions are the important features of these protocols. Futhermore, using these protocols a wide variety of imidazolone-fused isoquinolinone derivatives, pyrimidinone-fused isoquinolinone derivatives, a di-azapinone-fused isoquinolinone derivative and iminoisoindolinone derivatives were accessed in excellent to moderate yields.
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