ChemInform Abstract: Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones.

✍ Scribed by Michael C. Pirrung; Florian Blume

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199939186

✦ Synopsis

Rhodium-Mediated Dipolar Cycloaddition of Diazoquinolinediones.

-A useful method for the preparation of polyheterocyclic ring systems based on quinolines is reported. Both linear and angular furoquinoline products are obtained from the rhodium-catalyzed dipolar cycloaddition of diazo compounds with alkenes and alkynes. It is found that catalytic quantities of HCl enhance the yield and regiochemical control in the cycloaddition. The products can be further converted to naturally occurring alkaloids, such as isodictamnine (XVI).