A Novel Synthesis of Biologically Active Perfluoroalkyl N-Heterocyclic Compounds Using Organosilicon Reagents
使用有机硅试剂合成生物活性全氟烷基N-杂环化合物的新方法
基本信息
- 批准号:03640465
- 负责人:
- 金额:$ 1.34万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for General Scientific Research (C)
- 财政年份:1991
- 资助国家:日本
- 起止时间:1991 至 1992
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
N-Silyl-l-aza-allyl anions (1), generated from 3-methyl-5-(trimethylsilylmethyl)-isoxazole and aryl cyanides, reacted with perfluoro(2-methyl-2-pentane) (2) or 3-acethyl-4-methoxy-3-buten-2-one (3) to give the corresponding Rf or 4-Me pyridines (4) or (5) in high yields. The former product (4) was effectively converted into the corresponding 1,6-naphthyridine in good yield by hydrogenation of the isoxazole ring and the consecutive intramolecular cyclization in the presence of sodium hydoxide. On the other hand, 2-(Trimethylsilylmethyl)pyridine reacted with (2) in the presence of potassium fluoride to afford 2-pentafluoroethyl-3-trifluoromethyl-4H-quinolizin-4-one (6) in quantitative yield. The analogous reaction of the silyl derivatives of methylpyridines, methylquinolines, benzoxazole and benzothiazole gave the corresponding Rf-substituted compounds in good yields. The compound (6), furthermore, gave the methyl ester of the 3-carboxylic acid of (6) in high yield on treating with dimethyl sulfate whereas (6) quantitatively gave 2-pentafluoroethyl-4H-quinolizin-4-one (7) by decarboxylation after hydrolysis on treating with sulfuric acid. The mechanisms of these reactions were also discussed.
由3-甲基-5-(三甲基硅基甲基)异恶唑与芳腈反应生成的N-硅基-1-氮杂烯丙基阴离子(1)与全氟(2-甲基-2-戊烷)(2)或3-乙酰基-4-甲氧基-3-丁烯-2-酮(3)反应,高产率地得到相应的Rf或4-Me吡啶(4)或(5)。前一种产物(4)通过异恶唑环的氢化和在氢氧化钠存在下的连续分子内环化有效地转化为相应的1,6-萘啶。另一方面,2-(三甲基甲硅烷基甲基)吡啶与(2)在氟化钾存在下反应,以定量产率得到2-五氟乙基-3-三氟甲基-4H-喹嗪-4-酮(6)。甲基吡啶、甲基喹啉、苯并恶唑和苯并噻唑的甲硅烷基衍生物的类似反应以良好的产率得到相应的Rf取代化合物。此外,化合物(6)在用硫酸二甲酯处理时高产率地得到(6)的3-羧酸的甲酯,而(6)在用硫酸处理水解后通过脱羧定量地得到2-五氟乙基-4H-喹嗪-4-酮(7)。并对反应机理进行了讨论。
项目成果
期刊论文数量(22)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Takeo Konakahara: "One-Pot Synthesis of Pyrroles from N-Silyl-1-aza-allyl Anions" Heterocycles. 35. (1993)
Takeo Konakahara:“从 N-Silyl-1-aza-allyl 阴离子一锅法合成吡咯”杂环。
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- 影响因子:0
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T.Konakahara: "The Reaction of Nーsilylー1ーazaーallyl Anions with α,βーunsaturated Ketones" Bull.Chem.Soc.Jpn.,.
T.Konakahara:“N-silly-1-aza-allyl 阴离子与 α,β-不饱和酮的反应”Bull.Chem.Soc.Jpn.,。
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- 影响因子:0
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Takeo Konakahara: "A Novel Synthesis of 4-Methyl-, 4-oxo- and 4-Amino-3-(3-methyl-5-isoxazolyl)pyridine Derivatives via N-Silyl-1-aza-allyl Anion" Heterocycles. 33. 157-160 (1992)
Takeo Konakahara:“通过 N-甲硅烷基-1-氮杂烯丙基阴离子新型合成 4-甲基-、4-氧代-和 4-氨基-3-(3-甲基-5-异恶唑基)吡啶衍生物”杂环。
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- 影响因子:0
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Takeo Konakahara: "A Novel One-Pot Synthesis of Perfluoroalkylated Quinolizinones, Benzoxazolones, Benzothiazolones, and Their Benzo- or Pyrido-Derivatives" Proceedings of 3rd Inter- national Conference on High Technology, Chiba. 143-146 (1992)
Takeo Konakahara:“全氟烷基化喹啉酮、苯并恶唑酮、苯并噻唑酮及其苯并或吡啶并衍生物的新型一锅法合成”第三届国际高科技会议记录,千叶。
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- 影响因子:0
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T. Konakahara: "One‐Pot Synthesis of Pyrroles from N‐Silyl‐1‐azaallyl Anions" Heterocycles. 35. IN PRESS (1993)
T. Konakahara:“从 N-甲硅烷基-1-氮杂烯丙基阴离子一锅法合成吡咯”杂环,35。印刷中(1993 年)。
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KONAKAHARA Takeo其他文献
One-step Synthesis of Enynes from Aryl iodides, Internal alkynes and Alkynylsilane
由芳基碘化物、内炔烃和炔基硅烷一步合成烯炔
- DOI:
- 发表时间:
2009 - 期刊:
- 影响因子:0
- 作者:
SAKAI Norio;KOMATSU Ryosuke;UCHIDA Naoki;KONAKAHARA Takeo - 通讯作者:
KONAKAHARA Takeo
KONAKAHARA Takeo的其他文献
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{{ truncateString('KONAKAHARA Takeo', 18)}}的其他基金
A Novel Synthesis of Molecular-Targetting Indole Alkaloids and Elucidation of Anticancer Mechanism by Inducing Apoptosis
分子靶向吲哚生物碱的新合成及诱导细胞凋亡抗癌机制的阐明
- 批准号:
24590025 - 财政年份:2012
- 资助金额:
$ 1.34万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Synthesis of Highly-Functional DNA Binding Indole Alkaloids and Quinolones and Their Antitumor Activity
高功能DNA结合吲哚生物碱和喹诺酮类药物的合成及其抗肿瘤活性
- 批准号:
21590025 - 财政年份:2009
- 资助金额:
$ 1.34万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Synthesis of DNA-Binding Highly Functionalized Indole-alkaloid and Quinolone Derivatives and Their Function
DNA结合高功能化吲哚生物碱和喹诺酮衍生物的合成及其功能
- 批准号:
16550148 - 财政年份:2004
- 资助金额:
$ 1.34万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Synthesis of Biologically Active Perfluoroalkyl N-Heterocycles Using Organosilicon Reagents
使用有机硅试剂合成生物活性全氟烷基N-杂环
- 批准号:
01550681 - 财政年份:1989
- 资助金额:
$ 1.34万 - 项目类别:
Grant-in-Aid for General Scientific Research (C)
相似海外基金
Selective Electrosynthesis of Biologically Active Organofluorine Compound Using a Fluorine Mediator
使用氟介体选择性电合成生物活性有机氟化合物
- 批准号:
09650949 - 财政年份:1997
- 资助金额:
$ 1.34万 - 项目类别:
Grant-in-Aid for Scientific Research (C)