Benzofuran dioxetanes, a new class of mutagenic agents: Synthesis by photooxygenation of benzofuran derivatives

✍ Scribed by Adam, Waldemar ;Albrecht, Olaf ;Feineis, Erich ;Reuther, Irene ;Saha-Möller, Chantu R. ;Seufert-Baumbach, Petra ;Wild, Dieter

• Book ID: 102902279
• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 939 KB
• Volume: 1991
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199119910106

✦ Synopsis

Abstract

Tetraphenylporphine‐sensitized photooxygenation of benzofuran derivatives 1 afforded the corresponding benzofuran dioxetanes 2 in good yields. Allylic hydroperoxides 3 were formed regioselectively from 2,3‐dimethyl‐substituted benzofurans as minor products, except in the case of the benzofuran 1d, which gave predominantly the hydroperoxide 3d. The relative reactivities of the benzofurans toward singlet oxygen depended on the nature of substituents at the C‐2 and C‐3 positions of the furan rings. The benzofuran dioxetanes 2 were strongly mutagenic in the Salmonella typhimurium strain TA 100, their mutagenicity depending on the type of substituents of the dioxetane and of the benzo rings.