One-Pot Synthesis of 6-Methoxy-1,2,3,9-tetrahydro-4H- carbazol-4-one Oxime

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (03): 362-364. Previous Articles Next Articles

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6-甲氧基-1,2,3,9-四氢-4H-咔唑-4-酮肟的一锅合成

孙健，盛源，谢琼*，仇缀百

(复旦大学药学院药物化学教研室上海 201203)

收稿日期:2010-06-29 修回日期:2010-09-30 发布日期:2010-10-11
通讯作者: 谢琼 E-mail:xiejoanxq@gmail.com

One-Pot Synthesis of 6-Methoxy-1,2,3,9-tetrahydro-4H- carbazol-4-one Oxime

SUN Jian, SHENG Yuan, XIE Qiong, CHOU Zhui-Bai

(Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203)

Received:2010-06-29 Revised:2010-09-30 Published:2010-10-11
Contact: Qiong XIE E-mail:xiejoanxq@gmail.com

Abstract

6-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one oxime (3b) was synthesized by one-pot reaction. The combination of Fischer indole synthesis and oximation led to simplified process and increased productivity. This reaction could proceed in one pot in weak alkaline solution at mild temperature since oximation has facilitated the Fischer indole cyclization. Differences in tautomerization between carbonyl and oximyl were considered as the key factor that influenced the cyclization.

Key words: one-pot synthesis, Fischer indole synthesis, oximation, tautomerism

CLC Number:

R914

Cite this article

SUN Jian, SHENG Yuan, XIE Qiong, CHOU Zhui-Bai. One-Pot Synthesis of 6-Methoxy-1,2,3,9-tetrahydro-4H- carbazol-4-one Oxime[J]. Chin. J. Org. Chem., 2011, 31(03): 362-364.

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6-甲氧基-1,2,3,9-四氢-4H-咔唑-4-酮肟的一锅合成

One-Pot Synthesis of 6-Methoxy-1,2,3,9-tetrahydro-4H- carbazol-4-one Oxime

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