Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines and Evaluation of Antioxidant Properties

✍ Scribed by Ole Benny Østby; Bjørn Dalhus; Lise-Lotte Gundersen; Frode Rise; Aalt Bast; Guido R. M. M. Haenen

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 344 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200011)2000:22<3763::aid-ejoc3763>3.0.co;2-s

✦ Synopsis

Protocols for the synthesis of novel 1-substituted 7-cyano-2,3diphenylindolizines from the corresponding indolizinol have been developed, and the compounds' abilities to act as antioxidants, i.e. to inhibit lipid peroxidation in vitro, have been examined. 1-Bromo-7-cyano-2,3-diphenylindolizine 9 readily participates in Pd-catalysed coupling reactions with organotin, organozinc, and organoboron reagents. Similar treatment of the corresponding indolizinyl triflate 6, on the other hand, resulted only in partial cleavage of the triflate back to the indolizinol, except in reaction with 1-ethoxyethenyl(tributyl)tin. Here, the unexpected acetal (1-ethoxyethoxy)indolizine 10 was formed. The structure of 10 was de- [a