Tetrahedron Letters最新文献

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Visible light-driven innovative approaches for the synthesis of quinoline and isoquinoline based heterocycles 可见光驱动合成喹啉和异喹啉杂环化合物的创新方法

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-12-04 DOI: 10.1016/j.tetlet.2025.155922

Ravi Varala , Vittal Seema , Murali Mohan Achari Kamsali , Nahida Kousar , Mohamed Hussein , Mohammed Mujahid Alam

Heterocyclic compounds represent essential frameworks that are prevalent in nature and demonstrate intriguing biological and pharmaceutical properties. Quinoline and isoquinoline derived scaffolds represent a category of N-heterocyclic compounds that exhibit a wide array of biological properties. Reactions mediated by visible light have developed into a formidable instrument in organic synthesis over the last 15 years, transforming the methodologies employed by chemists in tackling complex bond-forming processes.

This review constitutes the most thorough examination to date of photochemical strategies for the synthesis of quinoline and isoquinoline derivatives, encompassing advancements in this domain from 2021 to the present. The organization is based on the categories of starting compounds, and it delves into synthetic strategies for the target compounds, accompanied by proposed reaction mechanisms. We anticipate that this compilation will inspire chemists to explore innovative, eco-conscious approaches for the synthesis of these and other biologically important nitrogen-rich heterocycles.

杂环化合物代表了自然界中普遍存在的基本框架，并表现出有趣的生物学和药学特性。喹啉和异喹啉衍生的支架是一类n -杂环化合物，具有广泛的生物学特性。在过去的15年里，可见光介导的反应已经发展成为有机合成领域一种强大的工具，改变了化学家在处理复杂键形成过程中所使用的方法。这篇综述是迄今为止对合成喹啉和异喹啉衍生物的光化学策略进行的最彻底的研究，涵盖了从2021年到现在这一领域的进展。该组织是基于开始化合物的类别，并深入研究目标化合物的合成策略，伴随着提出的反应机制。我们预计，这一汇编将激发化学家探索创新的，生态意识的方法来合成这些和其他生物上重要的富氮杂环。

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引用次数: 0

Urea-promoted simple and efficient synthesis of diverse and densely functionalized 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) in aqueous ethanol 尿素促进了4,4′-（芳基亚甲基）双（1h -吡唑-5-醇）在乙醇水溶液中的简单高效合成

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-12-04 DOI: 10.1016/j.tetlet.2025.155921

Selvaraj Mangalaraj , Suresh Rajamanickam , Kavin Loganathan , Suhesh Aseervatham , Rashinikumar Samandram , Parthiban Anaikutti

Urea-promoted, efficient and green methodology has been developed for the synthesis of a library of medicinally relevant 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) moieties using aromatic aldehydes and 3-methyl-1-phenyl-2-pyrazoline-5-one in good to excellent yield. This reaction displays broad functional group tolerance and affords a cost-effective, readily available, water-soluble and environmentally safe catalyst protocol for the quick synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) derivatives from readily available substrates. All the synthesized compounds were characterized by various analytical techniques such as FT-IR, ¹H (Proton) NMR, ¹³C (Carbon) NMR analysis and high-resolution mass spectrometry.

利用芳香醛和3-甲基-1-苯基-2-吡唑啉-5- 1，以尿素促进、高效和绿色的方法合成了一系列具有医学意义的4,4 ' -（芳基亚甲基）双（1h -吡唑醇-5-醇）基团，收率很高。该反应具有广泛的官能团耐受性，为从现成的底物快速合成4,4 ' -（芳基亚甲基）双（1h -吡唑-5-醇）衍生物提供了一种经济、容易获得、水溶性和环境安全的催化剂方案。通过FT-IR、1H（质子）核磁共振、13C（碳）核磁共振和高分辨率质谱等分析技术对合成的化合物进行了表征。

引用次数: 0

Synthesis of aza- and aza-carba-pterocarpens by electrophilic amination of arene C−H bonds 芳烃C−H键亲电胺化合成氮杂和氮杂碳翼香化合物

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-12-03 DOI: 10.1016/j.tetlet.2025.155919

Jannik Eckert, Lisa Marx, Tobias Sauter, Rafael Valentin, Andreas Speicher

Tetracyclic fused heterocycles of the aza-pterocarpen type are attracting increasing interest due to their various biological activities. We present a novel and straightforward synthesis of representative aza- and aza-carba-pterocarpens. For the first time, the Grignard-induced electrophilic amination of arene C−H bonds starting with o-nitrobiaryls was applied to this type of compound.

杂合四环杂环由于其丰富的生物活性而受到越来越多的关注。我们提出了一种新颖而直接的合成具有代表性的aza-和aza-carba-翼蕨烯。本文首次将以邻硝基为起始的芳烃C−H键的格氏诱导亲电胺化反应应用于这类化合物。

引用次数: 0

Base-promoted thermal cyclodebromination of β, β-dibrominated secondary enamides to 2,4-disubstituted oxazoles 碱促进β， β-二溴化仲胺热环溴化合成2,4-二取代恶唑

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-11-29 DOI: 10.1016/j.tetlet.2025.155910

Mengzhu Yu , Guangwei Yin , Yudi Hao , Xiaohui Yan , Fangyi Li

A new method has been developed for synthesizing 2,4-disubstituted oxazoles through base-promoted thermal cyclodebromination of β, β-dibrominated secondary enamides. This method does not require a transition metal or any external oxidants. Mechanistically, it is believed that the reaction is initiated by deprotonation of the secondary enamides, followed by a series of bond cleavage and formation events under thermal condition. Control experiments provided significant insights into the mechanism.

研究了β， β-二溴化仲胺的碱促进热环溴化合成2,4-二取代恶唑的新方法。这种方法不需要过渡金属或任何外部氧化剂。从机理上看，该反应是由仲胺的去质子化引起的，然后在热条件下发生一系列的键裂解和成键反应。对照实验提供了对机制的重要见解。

引用次数: 0

Recent advances in transition metal catalysis featuring Z-type ligands z型配体过渡金属催化研究进展

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-11-28 DOI: 10.1016/j.tetlet.2025.155909

Hikaru Takahashi, Ryo Murakami, Fuyuhiko Inagaki

Z-type ligands, characterized as σ-acceptors enhancing transition metal Lewis acidity, have recently emerged as powerful tools in transition metal catalysis. Although early studies were hampered by concerns over their instability and synthetic inaccessibility, subsequent design strategies involving rigid chelating frameworks and intramolecularly stabilized p-block elements (B, Al, Ga, Sb) have overcome these challenges, thereby revitalizing interest in Z-type ligand chemistry. These ligands stabilize intermediates, lower activation barriers, and enable new catalytic pathways. Notably, Z-type ligands enhance π-acid catalysis by increasing metal electrophilicity, thereby facilitating cyclization and hydroamination reactions. They have also proven effective in selective hydrogenations and in activating otherwise unreactive bonds, including E–F (E = Si, Ge, Sn) and acyl chlorides. The development of chiral Z-type ligands based on heavier elements (Sb, Bi) has further advanced asymmetric catalysis. Computational studies have further clarified how these ligands modulate the electronic properties of the metal center, influencing both reactivity and selectivity. This review summarizes recent progress in the development and application of Z-type ligands, highlighting their growing impact on modern synthetic chemistry.

z型配体以σ-受体为特征，增强了过渡金属的路易斯酸，近年来成为过渡金属催化的有力工具。尽管早期的研究受到对其不稳定性和难以合成的担忧的阻碍，但随后的设计策略包括刚性螯合框架和分子内稳定的p-嵌段元素（B, Al, Ga, Sb）克服了这些挑战，从而重新激发了对z型配体化学的兴趣。这些配体稳定中间体，降低活化障碍，并使新的催化途径成为可能。值得注意的是，z型配体通过增加金属亲电性来增强π-酸催化作用，从而促进环化和氢胺化反应。它们还被证明在选择性氢化和激活非活性键方面是有效的，包括E - f （E = Si, Ge, Sn）和酰基氯化物。基于重元素（Sb, Bi）的手性z型配体的发展进一步促进了不对称催化的发展。计算研究进一步阐明了这些配体如何调节金属中心的电子性质，影响反应性和选择性。本文综述了近年来z型配体的开发和应用进展，重点介绍了它们对现代合成化学日益增长的影响。

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引用次数: 0

The base-promoted one-pot reaction of dichloronaphthoquinone and aryl methylamine with S8 to construct naphtho[2,3-d]thiazole 碱促二氯萘醌和芳基甲胺与S8反应生成萘[2,3-d]噻唑

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-11-24 DOI: 10.1016/j.tetlet.2025.155882

Pei-Lin Qi, Chen-Xi Huang, Yu-Jin Li

The coupling reaction between 2,3-dichloro-1,4-naphthoquinone, benzylamine, and S₈ affords 2-aryl-substituted naphtho[2,3-d]thiazole-4,9-diones. This approach to the naphtho[2,3-d]thiazole ring had the advantages of inexpensive raw materials, no transition metals, and economic efficiency. A nucleophilic addition to C2 and C3 of dichloro-1,4-naphthoquinone was proposed for this conversion.

2,3-二氯-1,4-萘醌与苯胺和S8的偶联反应生成2-芳基取代萘[2,3-d]噻唑-4,9-二酮。该方法制备萘[2,3-d]噻唑环具有原料便宜、无过渡金属、经济高效等优点。提出了二氯-1,4-萘醌在C2和C3上的亲核加成反应。

引用次数: 0

Polystyrene-supported N-prolyl tetrapeptides catalyzed asymmetric Michael addition of aldehydes to nitroolefins 聚苯乙烯负载的n -丙基四肽催化非对称Michael加成醛到硝基烯烃

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-11-24 DOI: 10.1016/j.tetlet.2025.155908

Meng Yuan , Tian-Rui Lian , Tie-Ying Ding, Yang-Xing Liu, Chao-Shan Da

The polystyrene-supported N-prolyl tetrapeptide was disclosed to catalyze the asymmetric addition of aldehydes to nitroolefins with water as solvent, achieving high yields, good enantioselectivities, and excellent diastereoselectivities. The heterogeneous catalyst can be successfully recovered and reused at least five times without loss of stereoselectivity. The results demonstrated that the configuration of the Michael adduct depends on both the configuration of the N-terminal amino acid and whether the N-terminal residue is a prolyl residue or a primary amino acid. The secondary structure of the catalyst is also seriously responsible for the direction of the asymmetric induction.

利用聚苯乙烯负载的n -丙烯四肽，以水为溶剂催化醛与硝基烯烃的不对称加成反应，获得了高收率、良好的对映选择性和优异的非对映选择性。多相催化剂可以成功回收并重复使用至少五次而不损失立体选择性。结果表明，Michael加合物的构型既取决于n端氨基酸的构型，也取决于n端残基是脯氨酸残基还是初级氨基酸。催化剂的二级结构对不对称感应的方向也有重要影响。

引用次数: 0

Synthesis of polyfunctionalized carbazole aldehydes by a [4+2] annulation of ethyl 2-(1-alkyl-3-formyl-1H-indol-2-yl)acetate with alkynals [4+2]环化2-（1-烷基-3-甲酰基- 1h -吲哚-2-基）乙酸乙酯与烷基醇合成多功能化咔唑醛

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-11-23 DOI: 10.1016/j.tetlet.2025.155907

Bei Wei , Meng Xue , Aining Dong , Zungan Wang , Bin Liu , Shurong Ban

In our study, we report a general, mild, efficient, and practical method for synthesizing polyfunctionalized carbazole aldehydes. The synthesis is achieved through a secondary amine-catalyzed Michael-Aldol reaction between ethyl 2-(1-alkyl-3-formyl-1H-indol-2-yl)acetate and alkynals. This method provides a powerful alternative approach to access carbazole aldehyde frameworks in moderate to good yields (60–80 %).

在我们的研究中，我们报告了一种合成多功能化咔唑醛的一般、温和、高效和实用的方法。该合成是通过仲胺催化的2-（1-烷基-3-甲酰基- 1h -吲哚-2-基）乙酸乙酯和烷基醇之间的Michael-Aldol反应实现的。该方法为获得咔唑醛框架提供了一种强有力的替代方法，收率中等至较高（60 - 80%）。

引用次数: 0

Additive-, thiol-, and transition-metal-free thioesterification of polyfluoroarenes in water 多氟芳烃在水中无添加剂、无硫醇和无过渡金属的硫代酯化反应

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-11-21 DOI: 10.1016/j.tetlet.2025.155906

Ziyue Zhang , Mengqin Liu , Tao Qin , Heye Zhou , Bin Liu

We report an additive-free, thiol-free, and transition-metal-free thioesterification of polyfluoroarenes that uses potassium sulfide (K₂S) and acyl chlorides under operationally simple, one-flask conditions. In neat water, K₂S engages polyfluoroarenes in a defluorinative S_NAr to generate polyfluoroaryl sulfide anions (ArS) in situ, which are rapidly captured by acyl chlorides to afford the corresponding thioesters with high chemoselectivity, broad functional-group tolerance, and straightforward gram-scale scalability. The protocol accommodates diverse polyfluoroarene scaffolds alongside aliphatic, aromatic, and heteroaryl acyl chlorides, enabling late-stage functionalization of sensitive molecules. The applicability of this polyfluoroaryl thioester is demonstrated by its utility as a notably more reactive acylating agent relative to conventional thioesters. This platform provides a practical, concise, and scalable route to polyfluoroaryl thioesters and expands the scope of defluorinative CF functionalization in water.

我们报告了在操作简单的单烧瓶条件下，使用硫化钾（K₂S）和酰基氯化物进行无添加剂、无硫醇和无过渡金属的多氟芳烃硫代酯化反应。在纯水中，K₂S与脱氟SNAr中的多氟芳烃结合，原位生成多氟芳基硫醚阴离子（ArS），这些阴离子被酰基氯化物迅速捕获，从而产生相应的硫酯，具有高化学选择性、广泛的官能团耐受性和直接的克级可扩展性。该方案可容纳不同的多氟芳烃支架与脂肪族，芳香族和杂芳酰酰氯，使后期功能化的敏感分子。这种多氟基硫酯的适用性通过其作为一种相对于传统硫酯更具反应性的酰化剂的效用得到证明。该平台提供了一种实用、简洁、可扩展的途径来制备聚氟基硫酯，并扩大了氟氯化碳在水中功能化的范围。

引用次数: 0

Skleton rearrangement to prepare spirooxindolequinazolone 骨架重排制备螺呋辛多喹那唑酮

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-11-21 DOI: 10.1016/j.tetlet.2025.155899

Jiting Song , Xianheng Wang , Mingyun Liu , Changkuo Zhao

A series of novel spirooxindole quinazolones were designed and synthesized in high yields by a two-step procedure from substituted evodiamine derivatives. The structure of obtained target compounds were identified by ¹H NMR, ¹³C NMR, HRMS and X-ray spectrum.

以取代乙伏二胺衍生物为原料，设计并采用两步法高产地合成了一系列新型螺恶哚类喹唑酮类化合物。通过1H NMR、13C NMR、HRMS和x -射线谱对所得目标化合物的结构进行了鉴定。

引用次数: 0

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