Synthesis of Azapolycyclic Systems Based on the Indolizino[3,4-b]quinoline Skeleton − A Diastereoselective Entry to Potential Oligodentate Artificial Receptors

✍ Scribed by Oliver Temme; Tim Dickner; Sabine Laschat; Roland Fröhlich; Sirpa Kotila; Klaus Bergander

• Book ID: 102657834
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 901 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199804)1998:4<651::aid-ejoc651>3.0.co;2-z

✦ Synopsis

A convenient diastereoselective synthetic route to the molecular tweezer bis (indolizino[3,4-b]quinolyl)methane 9 and the rigid indolizino[7Ј,8Ј:2,3]quinolino[8,7-h]indolizino[8,7-b]quinolines 14, 15 as potential receptor molecules has been developed, involving double imine condensation followed by Lewis acid catalyzed biscyclization of prolinal-derived bis-(imines) 8 and 13, respectively. Whereas the use of SnCl 4 leads to the formation of the planar polycycle 15, the corresponding concave product 14 is formed in the presence of