Synthesis of 10-Benzyl-9-acridone and Its Reduction with NaBH4

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1803-1806. Previous Articles Next Articles

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10-苄基吖啶酮的合成及其与硼氢化钠还原反应研究

高春梅^a; 刘华臣^a; 蒋宇扬^*,a ; 谭春燕^a ; 曹德榕^*,b

(a广东省化学生物学重点实验室清华大学深圳研究生院深圳 518055)
(b华南理工大学化学科学学院广州 510640)

收稿日期:2008-01-21 修回日期:2008-03-19 发布日期:2008-10-20
通讯作者: 蒋宇扬*;曹德榕*

Synthesis of 10-Benzyl-9-acridone and Its Reduction with NaBH4

GAO, Chun-Mei^a ; LIU, Hua-Chen^a; JIANG, Yu-Yang^*,a ;
TAN, Chun-Yan^a ; CAO, De-Rong^*,b

(a Key Laboratory of Chemical Biology of Guangdong Province, the Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055)
(b College of Chemistry, South China University of Technology, Guangzhou 510640)

Received:2008-01-21 Revised:2008-03-19 Published:2008-10-20
Contact: JIANG, Yu-Yang*;CAO, De-Rong*

Abstract

A series of 10-benzyl-9-acridones were synthesized and their reduction with NaBH4 to 10-benzy1-9,10-dihydroacridine derivatives was developed. Acridone 1 reacted with benzyl chlorides 2 in NaH/DMF/KI to give 10-benzyl-9-acridones 3 in high yields. Subsequent reduction of 3 with NaBH4 gave 10-benzy1-9,10-dihydroacridine derivatives 4 with yields of 88%～96%. However, the expected 10-benzy1-9,10-dihydro-9-hydroxyacridine derivatives 4’ were not detected. Probably, 4’ is the first reduc-tion product, which is not stable and reduced to 4 by NaBH4 immediately.

Key words: acridone, 9,10-dihydroacridine, NaBH4, acridine

Cite this article

GAO, Chun-Mei^a ; LIU, Hua-Chen^a; JIANG, Yu-Yang^*,a ;
TAN, Chun-Yan^a ; CAO, De-Rong^*,b. Synthesis of 10-Benzyl-9-acridone and Its Reduction with NaBH4[J]. Chin. J. Org. Chem., 2008, 28(10): 1803-1806.

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10-苄基吖啶酮的合成及其与硼氢化钠还原反应研究

Synthesis of 10-Benzyl-9-acridone and Its Reduction with NaBH4

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