Convenient synthesis of 3-Hydroxyquinolines via dakin oxidation: A short synthesis of Jineol

[Display omitted] •Simple methodology for the synthesis of 3-hydroxy quinolines.•Unprecedented Dakin oxidation of quinoline-3-carboxaldehydes.•Substituted quinoline-3-carboxaldehydes are more suitable for Dakin oxidation.•Efficient total synthesis of quinoline alkaloid Jineol via Dakin oxidation. A...

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Bibliographic Details
Published in:Tetrahedron letters 2020-09, Vol.61 (36), p.152294, Article 152294
Main Authors: Ghorai, Sujit K., Dasgupta, Mayukh, Dutta, Piyali, Dumeunier, Raphael, Mal, Sanjib, Patre, Rupesh, Kuilya, Tapan Kumar, Pal, Sitaram, Manjunath, Bhanu N.
Format: Article
Language:English
Subjects:
3-Hydroxyquinoline
Dakin oxidation
Jineol
Quinoline
Quinoline-3-carboxaldehyde
Total synthesis
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Summary:[Display omitted] •Simple methodology for the synthesis of 3-hydroxy quinolines.•Unprecedented Dakin oxidation of quinoline-3-carboxaldehydes.•Substituted quinoline-3-carboxaldehydes are more suitable for Dakin oxidation.•Efficient total synthesis of quinoline alkaloid Jineol via Dakin oxidation. A convenient synthesis of 3-hydroxyquinolines has been described via unprecedented Dakin oxidation of quinoline-3-carboxaldehydes. Subsequently, application of the methodology to a high yielding synthesis of quinoline alkaloid Jineol (1) is reported.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152294