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Synfacts 2006(8): 0771-0771
DOI: 10.1055/s-2006-941973
DOI: 10.1055/s-2006-941973
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Three-Component Synthesis of Pyrano- and Furanoquinolines
S. V. More, M. N. V. Sastry, C-F. Yao*
National Taiwan Normal University, Taipei, Taiwan
Further Information
Publication History
Publication Date:
21 July 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200608/lookinside/thumbnails/10.1055-s-2006-941973-1.jpg)
Significance
A mild three-component aldehyde-aniline-enol ether synthesis of pyrano- and furanoquinolines via the Povarov reaction (see review below) under TMSCl-catalyzed conditions is reported. The reaction involving an aza-Diels-Alder step, proceeds in modest to excellent yields which appears not to be influenced greatly by substituent effects. However, higher trans:cis diastereomeric ratios of products are favored by use of aldehydes and anilines bearing electron-donating groups and by 3,4-dihydro-2H-pyran (n = 2) as the dienophile. In a solitary example, cyclohexanone was used to give a tetrahydrophenathridinone derivative in 87% yield.