ChemInform Abstract: A Cycloaddition Approach Toward the Synthesis of Substituted Indolines and Tetrahydroquinolines.

✍ Scribed by Albert Padwa; Michael A. Brodney; Bing Liu; Kyosuke Satake; Tianhua Wu

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199939043

✦ Synopsis

A Cycloaddition Approach Toward the Synthesis of Substituted Indolines and Tetrahydroquinolines.

-2-Aminofurans, prepared by using a number of different procedures, undergo intramolecular Diels-Alder reactions to give various indolines and tetrahydroquinolines, depending on the tether at the amino nitrogen. A new route to cyclic 2-amidofurans [cf. (XV)], exemplified by the formal synthesis of alkaloid hippadine (XVII) is also presented. 2-Amido-substituted oxazoles are cross-coupled with Tms-acetylene (XIV) to give intermediates containing the alkyne tether, which undergo cyclization at elevated temperatures to yield the desilylated product, e.g. (XVI).