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Benzofuran dioxetanes, a new class of mutagenic agents: Synthesis by photooxygenation of benzofuran derivatives
Author(s) -
Adam Waldemar,
Albrecht Olaf,
Feineis Erich,
Reuther Irene,
SahaMöller Chantu R.,
SeufertBaumbach Petra,
Wild Dieter
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910106
Subject(s) - benzofuran , chemistry , photooxygenation , furan , allylic rearrangement , singlet oxygen , photochemistry , medicinal chemistry , dioxetane , organic chemistry , oxygen , catalysis , chemiluminescence
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.