Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives

doi:10.6023/cjoc201404014

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2106-2118.DOI: 10.6023/cjoc201404014 Previous Articles Next Articles

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5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类化合物的简便合成

高文涛, 兰帅, 白仁青卓玛, 李阳

渤海大学超精细化学品研究所锦州 121000

收稿日期:2014-04-08 修回日期:2014-05-08 发布日期:2014-06-03
通讯作者: 高文涛 E-mail:isfc@bhu.edu.cn
基金资助:
辽宁省自然科学基金（No. 20120001）及辽宁省教育厅科学研究（No. L2013428）资助项目.

Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives

Gao Wentao, Lan Shuai, Bairenqing Zhuoma, Li Yang

Institute of Superfine Chemicals, Bohai University, Jinzhou 121000

Received:2014-04-08 Revised:2014-05-08 Published:2014-06-03
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20120201) and the Scinetific Research Foundation of the Education Department of Liaoning Province (No. L1013428).

1. Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives.PDF(8867KB)

Abstract

2-Methyl(ethyl)aniline 1a, 1b were first underwent the Sandmeyer reaction to give 7-methyl (ethyl) isatins 2a, 2b. The resulting 2a, 2b were then subjected to the bromination reaction with N-bromosuccinimide (NBS) using eco-friendly PEG-400 as solvent at room temperature to afford 5-bromo-7-methyl (ethyl) isatins 3a, 3b. Compounds 2a, 2b, 3a, 3b were further alkylated at the nitrogen atom to give the corresponding 1-alkylation-7-methyl (ethyl) isatins 4a～4j, and 1-alkylation-5-bromo-7-methyl(ethyl)isatins 5a～5j. Finally, 2a, 2b, 3a, 3b, 4a～4j, 5a～5j were subjected to the condensation reaction with thiosemicarbazide using dioxane as solvent and potassium carbonate as alkali to successfully synthesize 24 kinds of 5H-[1,2,4]triazine[5,6-b]indole-3-thiol derivatives 6a～6x. Most of compounds were new and their structures were confirmed by IR, MS, ¹H NMR and ¹³C NMR spectra and elemental analyses.

Key words: 7-methyl(ethyl)isatin, 5-bromo-7-methyl(ethyl)isatin, bromination, alkylation, 5H-[1,2,4]triazino-[5,6-b]-indole-3-thiol

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Gao Wentao, Lan Shuai, Bairenqing Zhuoma, Li Yang. Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives[J]. Chin. J. Org. Chem., 2014, 34(10): 2106-2118.

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5H-[1,2,4]三嗪并[5,6-b]吲哚-3-硫醇类化合物的简便合成

Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives

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