利用金屬離子產生親電性碳自由基，近年來已廣泛地應用在有機合成上。在這些金屬離子中，以醋酸錳(III)最受到重視，但硝酸鈰(IV)銨(CAN)同樣地也具有合成上的應用價值。
本實驗室一直對類化合物進行親電性自由基反應深感興趣，並藉由此反應，合成出苯[f]引朵(Benzo[f]indole)類化合物。
近年來許多文獻指出，很多天然物或人工合成的抗腫瘤藥物含有類為骨架的雜環化合物，利用本實驗室的方法，可以快速地經由醋酸錳(III)或鈰(IV)起始羰基自由基，並加成於?類上之後，得到含有以?類為主架構的雜環化合物。
在本報告中，將探討 (1) [i] 2-烷胺基-1,4-??化合物與雙酮基化合物以鈰(IV)起始氧化性自由基反應(式一)，[ii] 2-烷胺基-1,4-??化合物與β-酮基酯化合物以鈰(IV)起始氧化性自由基反應(式二)，[iii] 2-甲胺基-1,4-??化合物與1,3-環己二酮化合物以鈰(IV)起始氧化性自由基反應(式三)；(2) 2-烷胺基-1,4-苯?化合物與羰基化合物在醋酸錳(III)氧化下進行自由基反應(式四)，[ii] 2-烷胺基-1,4-苯?化合物與β-酮基酯化合物在醋酸錳(III)氧化下進行自由基反應(式五)。

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)

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