Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 49, Pages 16228-16232Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404633
Keywords
cycloaddition; furans; isoquinolines; pyridynes; silyl groups
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Funding
- JSPS KAKENHI [23790017, 25460018]
- Platform for Drug Discovery, Informatics, and Structural Life Science from MEXT
- University of Shizuoka
- Uehara Memorial Foundation
- Hoansha foundation
- Grants-in-Aid for Scientific Research [23790017, 25460018] Funding Source: KAKEN
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A four-step regioselective synthesis of multisubstituted isoquinoline derivatives from 3-bromopyridines was developed by the Diels-Alder (DA) reactions of 2-silyl-3,4-pyridynes with furans, followed by functional-group transformations. In particular, the silyl group at the C2-position of the 3,4-pyridynes played two important roles: firstly, it functioned as the directing group for the DA reaction, and secondly, it served to introduce diverse substituents at the C1-position of the isoquinolines by electrophilic ipso-substitution.
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