Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 6, Pages 2020-2031Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504335
Keywords
fluorescence; isoquinolines; Heck reaction; multicomponent reactions; photochromism
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Funding
- University of Genova
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft [Mu 1088/9-1]
- International Exchange Erasmus Student Network
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A convergent and diversity-oriented approach to the unusual furo[2,3-c]isoquinoline scaffold is presented. This serendipity-driven approach is characterized by an Ugi multicomponent reaction, which gives the substrate for a palladium-catalyzed insertion-alkynylation-cycloisomerization cascade to provide the furo[2,3-c]isoquinolines in moderate to high yield. Upon UV excitation, all representatives are intensively blue luminescent, as observed by the naked eye, and quantitative fluorescence spectroscopy reveals a considerable effect of the substitution pattern on the quantum yields. The electronic structure is semiquantitatively rationalized by DFT and time-dependent DFT calculations.
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