We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthesis of Functionalized Quinolines from 4-(o-Nitroaryl)- Substituted 3-Acyl-4,5-Dihydrofurans: Reductive Cyclization and C=C Bond Cleavage.
- Authors
Zaytsev, Sergey V.; Villemson, Elena V.; Ivanov, Konstantin L.; Budynina, Ekaterina M.; Melnikov, Mikhail Ya.
- Abstract
A new synthetic approach to functionalized quinolines was developed based on the application of Zn-AcOH system as a simple and efficient reductive agent towards 4-(onitroaryl)- 3-acyl-substituted 4,5-dihydrofurans. Reduction of 3-carbonyl-substituted dihydrofurans is accomplished by C=C double-bond cleavage in the dihydrofuran ring and 1,6-cyclization, which leads to 3,4-dihydroquinolines. The latter can be easily oxidized to quinolines or reduced to tetrahydroquinolines. For dihydrofuran-3-carboxylates, reduction proceeds with retention of the dihydrofuran ring and affords a tricyclic dihydrofuroquinoline core under harsher conditions. The proposed general reaction pattern was supported by results of DFT calculations. Moreover, a similar reductive system can be successfully applied in the conversion of dihydrofuran acyclic precursors, γ-(o-nitroaryl) α,β-unsaturated carbonyl compounds, into quinoline derivatives.
- Subjects
QUINOLINE derivatives; DIHYDROFURANS; RING formation (Chemistry); CARBON-carbon bonds; CHEMICAL synthesis; CHEMICAL reactions
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 19, p2814
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201700256