Development of new efficient rearrangement reactions of compounds bearing consecutive hetero atoms
具有连续杂原子的化合物的新型高效重排反应的开发
基本信息
- 批准号:15590032
- 负责人:
- 金额:$ 2.3万
- 依托单位:
- 依托单位国家:日本
- 项目类别:Grant-in-Aid for Scientific Research (C)
- 财政年份:2003
- 资助国家:日本
- 起止时间:2003 至 2006
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
We have developed the new rearrangement reactions of compounds with the two consecutive hetero atoms for the efficient preparations of highly functionalized compounds and heterocycles.1. The rearrangement reaction of acylenamines adjacent to a heteroatomWe have established a novel [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines for synthesis of indolines and indoles. Under the mild conditions, N-trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sigmatropic rearrangement followed by cyclization to give indolines. On the other hand, both cyclohexenyl N-trifluoroacetyl enehydrazine and acyclic N-trifluoroacetyl enehydrazine gave indoles in good yield. The rearrangement of enehydrazine carrying either an o-methoxy or an o-methyl groups gave the dienylimines. The N-trifluoromethanesulfonyl enehydrazine was converted into the rearranged product at low temperature. Similarly, we have found that [3,3]-sigmatropic rearrangement of O-aryloxime et … More hers took place smoothly during the course of trifluoroacetylation of 0-aryloxime ether at lower temperature to give the various benzofurans. Furthermore, short and practical syntheses of natural benzofurans were achieved without protection of the hydroxyl group in good overall yield.2. The rearrangement reaction of imines adjacent to a heteroatomWe have developed imino 1,2-Wittig rearrangement of the hydroximates for the first time. The feasibility of this rearrangement is dependent upon the structure the substrates. The rearrangement of Z-hydroximates proceeded smoothly to give the 2-hydroxyoxime ether in good yield while the corresponding E-isomer gave a mixture of E-and Z-hydroxyoxime ethers. This method was applied to the asymmetric synthesis of (+)-cytoxazone.3. The rearrangement reaction of amines adjacent to a heteroatomWe have found domino elimination-rearrangement-addition of alkoxy(arylmethyl)amines using organolithium and organomagnesium reagent. This method is suitable for the preparation of a-branched sec-arylamines. Furthermore, we have succeeded in the synthesis of cyclic compounds carrying an azepine ring widely found in biologically active compounds. Less
我们开发了具有两个连续杂原子的化合物的重排反应,以有效地制备高官能化化合物和杂环1。N-三氟乙酰基苯肼的[3,3]-σ向重排反应用于合成吲哚和吲哚。在温和的条件下,含环戊烯环的N-三氟乙酰基苯肼顺利地进行了[3,3]-Sigma重排,然后环合成了吲哚类化合物。另一方面,环己烯基N-三氟乙酰基苯肼和非环N-三氟乙酰基苯肼均以较高的产率得到吲哚。带有邻甲氧基或邻甲基团的苯肼重排得到二烯亚胺类化合物。N-三氟甲磺酰肼在低温下转化为重排产物。类似地,我们发现了O-芳酮肟和…的[3,3]-Sigmatroic重排在较低温度下0-芳肟醚的三氟乙酰化反应中,更多的HER反应顺利进行,得到了各种苯并呋喃类化合物。此外,在没有羟基保护的情况下,以良好的总收率实现了天然苯并呋喃的短而实用的合成。邻位亚胺的重排反应我们首次研究了羟基亚胺的1,2-Wittig重排反应。这种重排的可行性取决于底物的结构.Z-羟肟酸酯的重排反应顺利进行,得到了产率较高的2-羟基肟醚,而相应的E-异构体则生成了E-和Z-羟基肟醚的混合物。将该方法应用于(+)-环恶唑酮的不对称合成。有机锂和有机镁试剂对烷氧基(芳甲基)胺的消除-重排-加成反应。该方法适用于α-支链仲芳胺的制备。此外,我们还成功地合成了含有氮杂环的环状化合物,这些化合物广泛存在于生物活性化合物中。较少
项目成果
期刊论文数量(36)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
宮田 興子: "A convenient route to the furopyran core of dysiherbaine"Org.Biomol.Chem.. 1(5). 772-774 (2003)
Akiko Miyata:“通往 Dysiherbaine 呋喃吡喃核心的便捷途径”Org.Biomol.Chem.. 1(5) (2003)。
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
- 作者:
- 通讯作者:
宮田 興子: "Efficient [3,3]-sigmatropic rearrangement accelerated by trifluoroacetyl group : synthesis of benzofurans under mild conditions"Org.Biomol.Chem.. 1(2). 254-256 (2003)
Koko Miyata:“三氟乙酰基加速的高效[3,3]-σ重排:温和条件下苯并呋喃的合成”Org.Biomol.Chem.. 1(2)(2003)。
- DOI:
- 发表时间:
- 期刊:
- 影响因子:0
- 作者:
- 通讯作者:
Novel domino elimination-rearrangement-addition of N-alkoxy(arylmethyl) amines to N-alkyl arylamines
N-烷氧基(芳基甲基)胺与N-烷基芳基胺的新型多米诺骨牌消除-重排-加成
- DOI:
- 发表时间:2006
- 期刊:
- 影响因子:0
- 作者:Miyata;Okiko; Takeda;Norihiko; Kimura;Yasuo; Takemoto;Yoshiji; Tohnai;Norimitsu; Miyata;Mikiji; Naito;Takeaki.;宮田 興子
- 通讯作者:宮田 興子
Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
- DOI:10.1016/j.tet.2006.01.087
- 发表时间:2006-04
- 期刊:
- 影响因子:2.1
- 作者:O. Miyata;Norihiko Takeda;Y. Kimura;Y. Takemoto;N. Tohnai;M. Miyata;T. Naito*
- 通讯作者:O. Miyata;Norihiko Takeda;Y. Kimura;Y. Takemoto;N. Tohnai;M. Miyata;T. Naito*
Preparation of optically active a-hydroxy oxime ether by diastereoselective imino 1,2-Wittig rearrangement of hydroximates and its application to synthesis of (+)-cytoxazone.
肟酸盐非对映选择性亚氨基1,2-Wittig重排制备光学活性α-羟基肟醚及其在( )-cytoxazone合成中的应用。
- DOI:
- 发表时间:2005
- 期刊:
- 影响因子:0
- 作者:Miyata;Okiko; Hashimoto;Jun; Iba;Ryuuichi; Naito;Takeaki.
- 通讯作者:Takeaki.
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MIYATA Okiko其他文献
MIYATA Okiko的其他文献
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{{ truncateString('MIYATA Okiko', 18)}}的其他基金
Development of novel synthetic reactions based on mutual cooperation of nitrogen-oxygen bonds and multiple bonds
基于氮氧键和多重键相互配合的新型合成反应的发展
- 批准号:
26460024 - 财政年份:2014
- 资助金额:
$ 2.3万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
New evolution of continuous hetero-atomic chemistry
连续杂原子化学的新进展
- 批准号:
21590034 - 财政年份:2009
- 资助金额:
$ 2.3万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
Development of efficient bond cleavage-mediated bond formation reaction and synthesis of biologically active compounds
开发有效的键断裂介导的成键反应和生物活性化合物的合成
- 批准号:
19590026 - 财政年份:2007
- 资助金额:
$ 2.3万 - 项目类别:
Grant-in-Aid for Scientific Research (C)
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