Tetrahedron

On the reactions of 1, 3-isoquinolinediones with singlet oxygen

KQ Ling, JH Ye, XY Chen, DJ Ma, JH Xu

Index: Ling, Ke-Qing; Ye, Jia-Hai; Chen, Xian-Yang; Ma, De-Jian; Xu, Jian-Hua Tetrahedron, 1999 , vol. 55, # 30 p. 9185 - 9204

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Citation Number: 14

Abstract

Reactions of 1, 3-isoquinolinediones 5 and 4-alkylated 1, 3-isoquinolinediones 13 with singlet oxygen are entirely dominated by their enolization and proceed smoothly in benzene in the presence of pyridine as a base and a hydrogen bond acceptor. The products are triketones 6 and benzoisofuranones 7 for 5, and hydroperoxides 14, hydroxides 15 and benzoisofuranones 16 for 13. It was found that hydrolysis of 6 afforded the isoindolones 8 ...