Development of efficient method for construction of medium-sized heterocycles based on endo mode cyclization

基于内环化构建中型杂环的有效方法的开发

• 批准号: 14571998
• 负责人: MUKAI Chisato
• 金额: $ 2.24万
• 依托单位: KANAZAWA UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2002
• 资助国家: 日本
• 起止时间: 2002 至 2003
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-14571998/
• 关键词: endo mode cyclization; medium-sized ring; oxygen-containing heterocycle; nitrogen-containing heterocycle; phenylsulfonyl group; active methane group; phenylsulfinyl group; Baldwin rules; エンド型閉環; 含酵素ヘテロ環; スルホニル基; アレン; 含酸素複素環; スルフィニル基; マロン酸ジメチ

The base-catalyzed the endo mode ring-closing reaction of 1-allenyl sulfoxides having a suitable alkyl side chain with the4erininal oxygen atom proceed as to afford the corresponding 5〜7-menibered oxacycles.Changing the sulfinyl group of the allenes to ths sulfonyl group brought some improvement resulting in the formation of 5〜8-membered oxacycles.This novel endo mode ring-closing reaction of allenes was applied to the congeners possessing the terminal nitrogen functionality and active methane group to give the corresppnding cyclized products in acceptable yields.Thus, this method was demonstrated to be applicable to various kinds of allenes.

碱基催化的1-甲基磺氧化物的内托模式闭环反应具有合适的烷基侧链，具有4-甲基氧原子，以提供相应的5-7-7-含氧氧化氧化物，从而改变了Allenes sulfonyl群的sulfonyl群，从而改变了sulfonyl的sulfonyl群，从而导致了sulfonyl的新模式，从而导致5-8-8-8-8-8-8-8-8-8-8-8-8-将艾伦斯的反应应用于具有末端氮功能和活性甲烷基的同类物，以可接受的产量给出了相关的环化产物。

项目成果

Chisato Mukai, Minoru Kobayashi, Shoko Kubota, Shinji Kitagaki: "Construction of Azacycles Based on Endo Mode Cyclization of Allenes"The Journal Organic chemistry. 69(in press). (2004)

Chisato Mukai、Minoru Kobayashi、Shoko Kubota、Shinji Kitagaki：“基于艾伦烯的 Endo 模式环化构建氮杂环”有机化学杂志。

Chisato Mukai, Haruhisa Yamashita, Miyoji Hanaoka: "A New Entry to Oxacycles via Base-Catalyzed Endo Mode Cyclization of Allenyl Sulfoxides and Sulfones"Organic Letters. 3. 3385-3387 (2001)

Chisato Mukai、Haruhisa Yamashita、Miyoji Hanaoka：“通过烯基亚砜和砜的碱催化内藤模式环化获得氧杂环的新条目”有机快报。

Chisato Mukai, Rie Ukon, Norikazu Kuroda: "A new entry to carbocycles : synthesis of cyclopentene and cyclohexene derivatives through endo-mode ring closure of allenyl sulfones"Tetrahedron Letters. 44. 1583-1586 (2003)

Chisato Mukai、Rie Ukon、Norikazu Kuroda：“碳环的新入门：通过丙二烯基砜的内模式闭环合成环戊烯和环己烯衍生物”四面体快报。

Chisato Mukai: "A new entry to carbocycles : synthesis of cyclopentene and cyclohexene derivatives through endo-mode ring closure of allenyl sulfones"Tetrahedron Letters. 44. 1583-1586 (2003)

Chisato Mukai：“碳环的新入门：通过丙二烯基砜的内模式闭环合成环戊烯和环己烯衍生物”四面体快报。

Chisato Mukai.Rie Ukon.Norikazu Kuroda: "A New Entry to Carbocycles : Synthesis of Cyclopenten and Cyclohexene Derivatives Through Endo-Mode Ring Closure of Allenyl Sulfones"Tetrahedron Letters. 44・8. 1583-1586 (2003)

Chisato Mukai.Rie Ukon.Norikazu Kuroda：“碳环的新入门：通过烯基砜的内模闭环合成环戊烯和环己烯衍生物”Tetrahedron Letters 44・8（2003）。