Chinese Journal of Organic Chemistry >
Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives
Received date: 2014-04-08
Revised date: 2014-05-08
Online 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).
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.
Gao Wentao , Lan Shuai , Bairenqing Zhuoma , Li Yang . Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(10) : 2106 -2118 . DOI: 10.6023/cjoc201404014
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