引用本文:
王国喜, 彭聪虎. 5-甲氧基吲哚的合成[J]. 应用化学,
2002, 19(10): 1014-1015.
Citation: WANG Guo-Xi, PENG Cong-Hu. Synthesis of 5-Methoxyindole[J]. Chinese Journal of Applied Chemistry, 2002, 19(10): 1014-1015.
Citation: WANG Guo-Xi, PENG Cong-Hu. Synthesis of 5-Methoxyindole[J]. Chinese Journal of Applied Chemistry, 2002, 19(10): 1014-1015.
5-甲氧基吲哚的合成
摘要:
5-甲氧基吲哚是重要的有机合成中间体,可用于合成吲哚类衍生物,如5-甲氧基色胺和松果腺素等[1,2]。经典的Reissert法[3]以2-甲基-4-甲氧基硝基苯与草酸二乙酯经缩合、还原、脱羧而得,该路线最后一步脱羧所需温度过高、易炭化导致收率低而难以工业化;Kita等[4]以三甲硅基乙氧基甲酰(TEOC)将2-氨乙基-4-甲氧基苯酚中的氨基保护后,在乙腈-甲醇溶液中以高价碘试剂PIFA(phenyliodinebistrifluo roacetate)催化氧化得醌式亚氨的缩醛化合物,分子内成环时去掉保护基团TEOC,再以10%Pd/C处理而得5-甲氧基吲哚,该方法所用保护基制备困难,催化剂昂贵;Cho等[5,6]以对甲氧基苯胺与三乙醇胺为原料直接环合而得,但须在高压下进行,且使用了昂贵的三氯化钌为催化剂,因而失去了工业应用价值。
English
Synthesis of 5-Methoxyindole
Abstract:
5-Methoxyindole was synthesized in 4 steps starting from m-cresol through nitrosation oxidation, etherification, condensation and reduction-cyclization. The protecting piperidine group was at last removed from the enamine with Raney nickel as catalyst to give 5-methoxyindole. The total yield was 34.3%.
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Key words:
- methoxyindole
- / m-cresol
- / synthesis
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