Studies on quinones. Part 32. Regioselective synthesis of benz[b]phenantridines related to phenantroviridone

✍ Scribed by Jaime A. Valderrama; M.Florencia González; Claudio Valderrama

• Book ID: 104209386
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 622 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00278-1

✦ Synopsis

The Diels-Alder reaction of juglone (4) and bromojuglone 18 with l-cyclohexenecartx~xaldehyde dimethylhydrazone (3) is described. Through these cycloaddition reactions 8-hydroxy-1,2,3,4-tetrahydrobenz[b]phenantridin-7,12-dione (5) was obtained i n 55 and 78% yield, respectively. Oxidation of 5 to 8-hydroxybenz[b]phenantridin-7,12-dione ( 6) and 8-hydroxy-1,2,3A-tetrahydrobenz[b]phenantridin-1,7,12-trione (1 5) is also reported.