通过 (3 + 2) 取消α-替代乙烯酸和Bicyclo[1.1.0]butanes的模块化合成azidobicyclo[2.1.1]hexanes
Sai Hu1,2, Yuhong Gao1,2, Yuming Pan1
1Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang Province 310030, China.
我们开发了一种新方法来合成使用乙烯酸和乙烯酸[1.1.0]butanes. azidobicyclo[2.1.1]hexanes. 这些化合物可以转化为有价值的3-azabicyclo[3.1.1]heptene,展示它们的合成实用性.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 亚二环基是有价值的合成中间体.
- 合成它们的高效方法至关重要.
研究的目的:
- 开发一种温和而快速的合成亚齐多[2.1.1]hexanes的方法.
- 探索这些化合物的转化成其他有价值的结构.
主要方法:
- 正式 (3 + 2) 循环添加α-置换的亚酸乙烯和双环[1.1.0]布坦.
- 易斯酸催化 易斯酸催化
- 微波促进的重新排列.
- 铜 ((I) 催化Huisgen 1,3-双极循环添加. 铜 ((I) 催化Huisgen 1,3-双极循环添加.
主要成果:
- 在温和条件下成功合成了azidobicyclo[2.1.1]hexanes.
- 对广泛的α-替代乙烯酸酸盐的耐受性.
- 循环载荷管道的转化为3-azabicyclo[3.1.1]肝素.
- 通过进一步的功能化证明了实用性.
结论:
- 已经建立了一个新的和高效的途径,以 azidobicyclo[2.1.1]hexanes.
- 合成的化合物作为复杂的含异环的多功能前体.
- 该方法在有机合成中具有广泛的适用性.
更多相关视频
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
相关概念视频
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
