Electrophilic Free Radical Reaction Between 1,4-Amino-quinones and Carbonyl Compounds

• Main Authors: Chih-Chung Tseng, 曾志中
• Other Authors: Che-Ping Chuang
• Format: Others
• Language: zh-TW
• Published: 2002
• Online Access: http://ndltd.ncl.edu.tw/handle/40238114035535290774

碩士 === 國立成功大學 === 化學系碩博士班 === 90 === Organic synthesis using carbon center radicals generated by oxidants is current interest. Although Manganese (III) Acetate has received the most attention, it appears that cerium(IV) ammonium nitrate(CAN) would be a very useful reagent for the generation of electrophilic free radicals that can be addition to alkenes. In our laboratory, we are interesting in the electrophilic free radical reaction between 1,4-quinone and carbonyl compounds that initiated by manganese(III) acetate or CAN. In recently reports, there are many naturally occurring and synthetic compounds having a benzo[f]indole-4,9-dione or indole-4,7-dione skeleton that exhibit antitumor activity. We can synthesis these skeletons one-pot by treating 2-amino-1,4-quinone with carbonyl compounds in the presence of CAN or manganese(III) acetate. In this report, we describe our results on：(1) [i] cerium(IV) initiated oxidative free radical reaction between 2-amino-4-naphthoquinone and 1,3-diketone compounds.(eq.1) [ii] cerium(IV) initiated oxidative free radical reaction between 2-amino-1,4-naphthoquinone and β-ketoesters.(eq.2) [iii] cerium(IV) initiated oxidative free radical reaction between 2-methylamino-1,4-naphthoquinone and 1,3-cyclohexadiones.(eq.3) (2) [i] manganese(III) acetate initiated oxidative free radical reaction between 2-alkylamino- 1,4-benzoquinone and carbonyl compounds.(eq.4) [ii] manganese(III) acetate initiated oxidative free radical reaction between 2-alkylamino-1,4-benzoquinone and 1,3-dicarbonyl compounds. (eq.5)