Dye-sensitized photooxygenations of 1,3-isoquinolinediones

✍ Scribed by Ling Ke-Qing; Ji Gang; Cai Hu; Xu Jian-Hua

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 302 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)00344-x

✦ Synopsis

Singlet oxygen reactions of 1,3-isoquinolinediones la-le could be sensitized by the anionic sensitizer Rose Bengal (RB) in methanol or by retraphenylporphin (TPP) in the presence of pyridine as a base and a cosolvent in benzene. The products are the corresponding 1,3,4-isoquinolinetriones Za-2e and methyl 1-hydroxy-3-oxoisoindole-l-carboxylates 3b-3e in methanol and the triketones Za-2e and the 3-hydroxy-3alkyl

(aryl)aminocarbonylbenzoisofuran-l-ones 4b-4e in benzene-pyridine. TPP sensitized photooxygenations of the I-alkylated 1,3-isoquinolinediones Sa-5c yielded the 4-alkyl-4.hydroxy-1,3-isoquinolinediones 6a-6c, the 4-alkyl-4-hydroperox-1.3~isoquinolinediones 7a-7c and the 3-alkylJ-hydroxybenzoisofuran-l-ones Sa-(lb. Reaction mechanisms have been proposed.