1,2-二皮里米丁合成通过介导的基,基和基的多元组件合
Rachel J Dunscomb1, Connor W Frye1, Xavier Murray1
1Department of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, USA. itonks@umn.edu.
研究人员开发了一种新的模块化合成方法,用于未经探索的1,2-二二胺. 这种多元组分反应利用,,化物和化物复合物,为这些生物活性核提供了一条新的途径.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 1,2-二基胺基架存在于各种生物活性化合物中.
- 由于有限的合成方法,合成1,2-二二皮里米丁区域异构体具有挑战性.
研究的目的:
- 开发一种新的,模块化和多元组件合成途径,以获得1,2-二二.
- 为了克服这些重要异环化合物的可访问合成途径的稀缺性.
主要方法:
- 一种涉及,亚,化物和化物复合物的多组分反应.
- 形成一个关键的二甲酸循环中间体.
- 随后的 [2+2] - 循环添加,循环逆转和电循环化步骤.
主要成果:
- 使用开发的模块化方法,成功合成了1,2-二二皮里米丁.
- 展示了一种新的合成策略,通过二酸乙循环中间体进行.
- 反应序列包括阿尔代添加,循环回归到1,5-亚亚二烯,以及电循环.
结论:
- 报告的方法提供了一种高效和模块化的获取1,2-dihydropyrimidines.
- 这项工作扩大了合成工具箱,以获取尚未探索的二皮里米丁区域异构体.
- 该战略利用先前用于和α-胺合成的介导途径.
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相关概念视频
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
