A Novel Synthesis of Indole and Quinoline Derivatives from Aniline and 1, 2- or 1, 3-Diols
由苯胺和 1, 2- 或 1, 3- 二醇合成吲哚和喹啉衍生物的新方法
基本信息
- 批准号:01850192
- 负责人:
- 金额:$ 4.29万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for Developmental Scientific Research (B).
- 财政年份:1989
- 资助国家:日本
- 起止时间:1989 至 1990
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
1. (1) Syntheses of Indole Derivatives from 2- (2-Aminophenyl) ethanol and 2- (2-Nitrophenyl) ethanol : When 2- (2-aminophenyl) ethanols (3), which were easily prepared by condensation between the corresponding 2-nitrotoluene (1) and aldehydes followed by reduction, were treated with a catalytic amount of RuCl_2(PPh_3)_3 (2 mol%) under reflux in toluene for 6 h, the corresponding indoles (4) were readily obtained in high to excellent yields (73-100 %).1. (2) Plots of -ln vs time were linear over 70 % conversions of (3), where x is the amount of indoles (4) formed and a_0 is the amount of (3) charged. Furthermore, a straight line with a zero intercept was obtained on plotting the observed rate constants against the different initial catalyst concentrations ([RuCl6.10 x 10-2.44 x 10 mol dm^<-3>). Thus the rate law for the present indole synthesis is expressed by the following equation.d[(4)]/dt=kappa_<obs>[RuCl_2(PPh_3)_3]_0[(3)]1. (3) With a heterogeneous (Pd/C or Rh/C) and homogeneous (RuCl_2(PPh_3)_3 binary catalyst system, indoles were afforded in one pot from 2- (2-nitrophenyl) ethanols (2) under a hydrogen atmosphere.2. (1) Synthesis of Indole from Aniline and Ethylene Glycol : When the reaction of aniline with ethylene glyol was performed (aniline/ethylene glycol=1.0/1.5) in the presence of a catalytic amount of RuCl, 1.4-diphenylpiperazine was mainly obtained. However, when the molar ration of aniline/ethylene glycol was increased from 1.0/1.5 to 10/1.0, indole was obtained in 8 % yield together with a considerable amount of N, N'-diphenylethylenediamine. At this stage, RuClO - dppe is the most suitable catalyst system for the synthesis of indole from aniline and ethylene glycol (18 % yield).2. (2) N- (Trimethylsilyl) aniline and acetanilide, which were protected compounds of aniline, did not react with ethylene glycol and the corresponding indoles were not obtained at all.
1.以2-(2-氨基苯基)乙醇和2-(2-硝基苯基)乙醇为原料合成吲哚类化合物:将2-(2-氨基苯基)乙醇(1)与醛缩合后还原而成的2-(2-氨基苯基)乙醇(3),在甲苯中回流6h,用RuCl2(PPh_3)_3(2mol%)催化剂处理6h,即可得到吲哚类化合物(4),产率可达73-100%。(2)-ln与时间的关系曲线在(3)的70%转化率范围内呈线性关系,其中x是吲哚(4)的生成量,a_0是(3)的带电量。此外,通过绘制不同初始催化剂浓度([RuCl6.10×10-2.44×10moldm^<;-3>;)]的观察到的速率常数,得到了一条零截距直线。在均相(Pd/C或Rh/C)和均相(RuCl2(PPh3)3)二元催化体系下,2-(2-硝基苯基)乙醇(2)在氢气气氛下一锅合成吲哚。(1)由苯胺和乙二醇合成吲哚:当苯胺与乙二醇合成时(苯胺/乙二醇=1.0/1.5),在一定量的RuCl3存在下,主要生成1.4-二苯基哌嗪。当苯胺/乙二醇摩尔比从1.0/1.5增加到10/1.0时,吲哚的产率为8%,同时还生成了相当数量的N,N‘-二苯乙二胺。在此阶段,RuClO-dppe是最适合由苯胺和乙二醇合成吲哚的催化剂体系(产率18%)。(2)受保护的N-(三甲基硅基)苯胺和乙酰苯胺不与乙二醇反应,也不生成相应的吲哚。
项目成果
期刊论文数量(7)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Yasushi Tsuji: "RutheniumーCatalyzed Dehydrogenative NーHeterocyclization:Indoles from 2ーAminophenethyl Alcohols and 2ーNitrophenethyl Alcohols" The Journal Organic Chemistry. 55. 580-584 (1990)
Yasushi Tsuji:“钌催化脱氢 N-杂环化:2-氨基苯乙醇和 2-硝基苯乙醇的吲哚”有机化学杂志 55. 580-584 (1990)。
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
- 作者:
- 通讯作者:
Yoshihisa Watanabe: "Novel Organic Syntheses Using Group VIII Metal Complexes" Journal of Synthetic Organic Chemistry, Japan. Vol. 47. 1132-1145 (1989)
Yoshihisa Watanabe:“使用第 VIII 族金属配合物的新型有机合成”,合成有机化学杂志,日本。
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
- 作者:
- 通讯作者:
Yasushi Tsuji: "Ruthenium-Catalyzed Dehydrogenative N-Heterocyclization:Indoles from 2-Amino Alcohls and 2-Nitrophenethyl Alcohols" Journal of Organic Chemistry. 55. 580-584 (1990)
Yasushi Tsuji:“钌催化脱氢 N-杂环化:来自 2-氨基醇和 2-硝基苯乙醇的吲哚”有机化学杂志。
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
- 作者:
- 通讯作者:
渡部 良久: "VIII族金属錯体を用いる新規合成反応の開発" 有機合成化学協会誌. 47. 1132-1145 (1989)
Yoshihisa Watanabe:“使用第 VIII 族金属配合物开发新的合成反应”有机合成化学学会杂志 47. 1132-1145 (1989)。
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
- 作者:
- 通讯作者:
Yasushi Tsuji: "Ruthenium-Catalyzed Dehydrogenative N-Heterocyclization : Indoles from 2-Aminophenethyl Alcohols and 2-Nitrophenethyl Alcohols" The Journal of Organic Chemistry. Vol. 55. 580-584 (1990)
Yasushi Tsuji:“钌催化脱氢 N-杂环化:2-氨基苯乙醇和 2-硝基苯乙醇中的吲哚”有机化学杂志。
- DOI:
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- 影响因子:0
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WATANABE Yoshihisa其他文献
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