从1,3-Butadiynamides中合成2-Alkoxyquinolines的帕拉多催化级联合成
Illia Lenko1, Alexander Mamontov1, Carole Alayrac1
1Laboratoire de Chimie Moléculaire et Thio-organique (LCMT), CNRS UMR 6507, ENSICAEN, Université de Caen, Normandie Univ, 6 Bd Maréchal Juin, 14050 Caen, France.
Molecules (Basel, Switzerland)
|August 10, 2024
概括
一种新的催化方法可以有效地从1,3-丁胺基中合成2-氧基诺林衍生物. 这种新的级联反应在温和条件下为复杂的素结构提供了一种简化方法.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 催化剂是一种催化剂.
背景情况:
- 传统的2 - 基诺林的合成涉及2 - 诺的化,往往需要严苛的条件.
- 为异环化合物开发高效的新合成路径仍然是有机化学的一个关键挑战.
研究的目的:
- 揭示一种新型的驱动级联反应,用于合成2 - - 基诺林衍生物.
- 建立一个新的策略,以新组装的林核.
主要方法:
- 帕拉催化反应级联使用N-(2-二) -N-托西尔-1,3-二胺基.
- 使用初级酒精作为外部核友.
- 在温和反应条件下进行单批量转化.
主要成果:
- 选择性合成各种功能化的4-基-2-氧基诺林.
- 从1,3-butadiynamides开始,证明了一条新的诺林衍生物的途径.
- 在级序列中成功应用催化剂.
结论:
- 开发的方法提供了一个有效和有选择的途径,以2-alkoxyquinoline衍生物.
- 这种新的策略在林合成的经典方法上提供了优势.
- 催化级联反应代表了异环化学的重大进步.
相关概念视频
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
2.1K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.1K
Preparation of 1° Amines: Azide Synthesis
3.9K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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...
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...
3.9K
Preparation of Alkynes: Dehydrohalogenation
15.7K
Introduction
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.
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.
15.7K
Radical Chain-Growth Polymerization: Overview
2.4K
Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
2.4K
Preparation of Epoxides
7.5K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
7.5K
Preparation of 1° Amines: Gabriel Synthesis
3.5K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.5K


