Tetrahedron最新文献

英文中文

Green-light/oxygen cooperative RFTA catalysis: One-pot debenzylation-acylation of N-benzyltetrahydroisoquinolines to access 3,4-dihydroisoquinolin-1(2H)-one 绿光/氧协同RFTA催化：n-苄基四氢异喹啉的一锅脱苯酰化反应得到3,4-二氢异喹啉-1(2H)- 1

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-29 DOI: 10.1016/j.tet.2025.135073

Hao Lan , Lei Ding , Yuhan Wang , Yunfei Li , Yu Lin , Weizhi Sun , Long Jiang , Chao Xu

Riboflavin 2′,3′,4′,5′-tetraacetate (RFTA) is a classic enzyme-mimetic photocatalyst that has demonstrated excellent catalytic performance in various oxidation reactions. In this study, we found that RFTA, in the presence of visible light and oxygen, can promote the cleavage of C(sp³)-N bonds and achieve one-pot oxidative amidation to construct 3,4-dihydroisoquinolin-1(2H)-one, a heterocyclic core widely present in many bioactive molecules, with a yield of 72 %. The reaction proceeds smoothly at room temperature and atmospheric pressure under 520 nm light irradiation using N-benzyl-1,2,3,4-tetrahydroisoquinoline as the substrate, without the need for precious metals, stoichiometric oxidants, or added bases, and is operationally simple. Preliminary mechanistic studies suggest that the reaction may first undergo single-electron transfer (SET), followed by a light-induced proton-coupled electron transfer (PCET) process, which cooperatively achieves the selective cleavage of the C(sp³)-N bond and the site-specific oxidation of the C(sp³)-H bond, thereby obtaining high chemical selectivity. Although this method still has certain limitations, we hope that this initial exploration can provide a useful supplement to the application of RFTA in biomimetic photocatalysis and offer a mild and practical new strategy for the synthesis of dihydroisoquinolinone skeletons with drug value.

核黄素2 ',3 ',4 ',5 ' -四乙酸酯（RFTA）是一种经典的模拟酶光催化剂，在各种氧化反应中表现出优异的催化性能。在本研究中，我们发现RFTA在可见光和氧气的存在下，可以促进C(sp3)-N键的裂解，实现一炉氧化酰胺化，构建广泛存在于许多生物活性分子中的杂环核心3,4-二氢异喹啉-1(2H)- 1，产率为72%。该反应以n -苄基-1,2,3,4-四氢异喹啉为底物，在520 nm光照射下，在室温常压下顺利进行，不需要贵金属、化学计量氧化剂或添加碱，操作简单。初步机理研究表明，该反应可能先进行单电子转移（SET），然后进行光诱导质子耦合电子转移（PCET）过程，这两个过程协同实现了C(sp3)-N键的选择性裂解和C(sp3)-H键的位点特异性氧化，从而获得较高的化学选择性。虽然该方法仍有一定的局限性，但我们希望这一初步探索能够为RFTA在仿生光催化中的应用提供有益的补充，并为具有药物价值的二氢异喹啉酮骨架的合成提供一种温和实用的新策略。

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引用次数: 0

Synthesis of polysubstituted cyclopropanes via [2 + 1] cycloaddition reaction of acyclic α,β-unsaturated imines with α-bromomalonate 无环α，β-不饱和亚胺与α-溴丙酸盐[2 + 1]环加成反应合成多取代环丙烷

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-28 DOI: 10.1016/j.tet.2025.135072

Kai-Kai Wang , Qing Xu , Xia-Shi Gao , Liang-Man Wu , Yue-Yao Ma , Li-Fang Yang , Rongxiang Chen

In this study, we describe a domino reaction involving acyclic α,β-unsaturated imines as C2 synthon with α-bromomalonate, leading to the formation of polysubstituted cyclopropanes via a Michael-initiated ring-closure/cyclopropanation sequence under mild conditions. This approach enables the synthesis of a diverse array of cyclopropanes bearing two adjacent tertiary stereogenic centers, achieving high yields (up to 98 %) with excellent chemo-, regio-, and diastereoselectivities (all cases >25:1 dr). Furthermore, the synthetic utility of this methodology is demonstrated through late-stage functionalization and the modification of drug-like molecules, underscoring its potential in complex molecule synthesis. The structure of a representative product was unambiguously confirmed by X-ray crystallography.

在这项研究中，我们描述了一个多米诺骨牌反应，涉及无环α，β-不饱和亚胺作为C2与α-溴丙酸盐合成，在温和条件下通过迈克尔引发的环闭合/环丙烷化序列生成多取代环丙烷。这种方法能够合成具有两个相邻的三级立体中心的各种环丙烷，具有优异的化学选择性、区域选择性和非对映选择性（所有案例>；25:1 dr），产率高达98%。此外，该方法的合成效用通过后期功能化和药物样分子的修饰得到证明，强调了其在复杂分子合成中的潜力。代表性产物的结构被x射线晶体学明确证实。

引用次数: 0

A new synthesis process of N-sulfonyl pyrazoles from sulfonyl hydrazines and β-diketones promoted by deep eutectic solvents 以磺酰肼和β-二酮为原料，在深度共晶溶剂催化下合成n -磺酰吡唑

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-26 DOI: 10.1016/j.tet.2025.135071

Tongyue Wu , Zhuoran Sun , Yuxin Cheng , Xu Zhu , Zhi Li , Yongheng Shi , Jingli Liu , Hui Guo , Hao Yan

Deep eutectic solvents have good biodegradability, low volatility, and efficient reusability. In the present work, deep eutectic solvents were used as solvents and catalysts to promote the cyclization reaction of sulfonylhydrazine compounds with β-dicarbonyl compounds, which is highly efficient and easy to operate. In addition, the post-treatment is simple without complicated post-processing such as column chromatography purification. The new synthesis process has good versatility. It is suitable for industrialized-scale production.

深共晶溶剂具有良好的生物降解性、低挥发性和高效的可重复使用性。本研究采用深共晶溶剂作为溶剂和催化剂，促进磺酰肼类化合物与β-二羰基类化合物的环化反应，反应效率高，操作简便。此外，后处理简单，无需柱层析纯化等复杂后处理。新合成工艺具有良好的通用性。适合工业化规模生产。

引用次数: 0

Access to 2-aminoquinolines from 2-vinylanilines and isothiocyanates via electrochemically induced desulfurative cyclization 通过电化学诱导脱硫环化从2-乙烯苯胺和异硫氰酸酯中获得2-氨基喹啉

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-25 DOI: 10.1016/j.tet.2025.135069

Wenxue Li , Zhenjie Qi , Zhenyu An , Yinjun Wei , Boyue Lin , Wenxin Chen , Yafeng Liu

An efficient electrochemical oxidation cyclization of 2-vinylanilines and isothiocyanates has been achieved for the synthesis of 2-aminoquinolines via NaI-mediated desulfurative cyclization. The protocol is further characterized by its high yield, broad substrate scope, and operational simplicity. Mechanistic studies reveal that the reaction involves the formation of a thiourea intermediate from 2-vinylanilines and isothiocyanates under electrochemical oxidation.

通过nai介导的脱硫环化，实现了2-乙烯基苯胺和异硫氰酸酯的高效电化学氧化环化合成2-氨基喹啉。该协议的进一步特点是其高收率，广泛的衬底范围和操作简单。机理研究表明，该反应涉及2-乙烯苯胺和异硫氰酸酯在电化学氧化作用下生成硫脲中间体。

引用次数: 0

The named reaction toolbox for COF synthesis: controlling crystallinity, stability, and performance COF合成的命名反应工具箱：控制结晶度、稳定性和性能

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-24 DOI: 10.1016/j.tet.2025.135070

Karishma Tiwari , Garima Pandey

Covalent organic frameworks (COFs) have rapidly emerged as a versatile class of highly crystalline porous polymers with tunable functionalities showing broad applications in the field of gas storage, catalysis, energy storage, sensing, drug delivery, and hydrogen evolution, etc. Fundamental to COF Chemistry is dynamic covalent chemistry (DCC), which allows error corrections during reversible bond formation to produce well-ordered frameworks. Several named reactions governed by DCC have been exploited for COF synthesis. This review provides a critical evaluation of fundamental reversible boronic acid condensation and key named reactions, including highly reversible Schiff base condensation, as well as reactions with low to moderate reversibility or irreversible nature, particularly Knoevenagel condensation, aldol condensation, Horner–Wadsworth–Emmons (HWE) condensation, Suzuki-type cross-coupling, Sonogashira coupling, and the aza-Diels–Alder reaction. Each of these reactions yields COFs with distinct structures and functionalities determined by the extent of their reaction reversibility. COFs synthesized through reversible condensation exhibit high crystallinity but limited stability, whereas frameworks produced by an irreversible approach show enhanced stability at the expense of crystallinity. Moreover, robustness in COFs can be improved by combining reversible and irreversible reactions or through post-synthetic modifications.

共价有机框架（COFs）作为一种具有可调功能的多用途高结晶多孔聚合物迅速兴起，在储气、催化、储能、传感、药物传递和析氢等领域显示出广泛的应用。COF化学的基础是动态共价化学（DCC），它允许在可逆键形成过程中进行错误修正，以产生有序的框架。几种命名的由DCC控制的反应已被用于合成COF。本文综述了基本可逆硼酸缩合和关键命名反应，包括高度可逆的Schiff碱缩合，以及低到中等可逆性或不可逆性质的反应，特别是Knoevenagel缩合，aldol缩合，Horner-Wadsworth-Emmons （HWE）缩合，suzuki型交叉偶联，Sonogashira偶联和aza-Diels-Alder反应。每一种反应产生的COFs都具有不同的结构和功能，这取决于它们的反应可逆性的程度。通过可逆缩合合成的COFs具有较高的结晶度，但稳定性有限，而通过不可逆缩合制备的框架则以牺牲结晶度为代价提高了稳定性。此外，COFs的鲁棒性可以通过结合可逆和不可逆反应或通过合成后修饰来提高。

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引用次数: 0

Mild and regioselective iodination of 3,5-disubstituted isothiazoles with N-iodosuccinimide and trifluoroacetic acid 用n -碘琥珀酰亚胺和三氟乙酸对3,5-二取代异噻唑进行轻度和区域选择性碘化

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-22 DOI: 10.1016/j.tet.2025.135068

Wen Yang , Ziyi Xu , Jiawei Bai , Hongyu Qiu , Zhongzhong Cao , Xin Min , Xuerui Yang , ChangChao Zhan , Qingchun Huang , Jiayan Pan , Zhongxin Li , Lidong Lai , Shaomin Ji

Combining N-iodosuccinimide (NIS) and trifluoroacetic acid (TFA) offers an efficient method for the iodination of a wide range of 3,5-disubstituted isothiazoles at room temperature, as demonstrated in this paper. The results indicate that when the C5 position of isothiazole ring is not the substituent of OCH₃Ph, the corresponding C4-mono-iodoisothiazoles are obtained in high yields with excellent regioselectivity, while when the C5 position of isothiazole ring is the substituent of OCH₃Ph, the corresponding diiodo and triiodoisothiazoles were synthesized. Additionally, both of bromination and chlorination of 3,5-disubstituted isothiazoles can also occur efficiently. Moreover, the versatility of the method is demonstrated by the iodination of isoxazoles and isoselenazoles.

结合n -碘琥珀酰亚胺（NIS）和三氟乙酸（TFA）提供了一种在室温下广泛的3,5-二取代异噻唑碘化的有效方法。结果表明，当异噻唑环的C5位置不是OCH3Ph取代基时，可以高收率地合成相应的c4 -单碘异噻唑，且具有良好的区域选择性；当异噻唑环的C5位置是OCH3Ph取代基时，可以合成相应的二碘和三碘异噻唑。此外，3,5-二取代异噻唑的溴化和氯化反应也能有效发生。此外，通过异恶唑和异硒化唑的碘化证明了该方法的通用性。

引用次数: 0

Metal-catalyzed azide-alkyne cycloaddition-click chemistry: an update (2016–2025) 金属催化叠氮化物-炔环加成-点击化学：更新（2016-2025）

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-21 DOI: 10.1016/j.tet.2025.135061

Subhasis Samai , Sanghamitra Atta , Maya Shankar Singh

In 2002, the ground-breaking concept, known as Click Chemistry, was independently presented by Sharpless and Meldal. The reaction involves the advent of Cu(I)-catalyzed Huisgen type 1,3-dipolar cycloaddition known as copper-catalyzed azide-alkyne cycloaddition (CuAAC) to yield the 1,4-disubstituted 1,2,3 triazoles in a regioselective manner. Later on, several other metals such as Ni, Rh, Ir, Zn, Ag etc. are used, and non-metal pathways like the electrochemical method and thermal method have also been developed for the azide-alkyne cycloaddition (AAC). Click chemistry promotes chemical reactions that enable the connection of two species in a simple and selective way, with few or no by-products under mild conditions. The extensive applications of this reaction in several industries have made it a booming research area. Due to the triazole linkage's characteristics as a peptide mimic, this chemistry also facilitates bioconjugation and peptide ligation. Herein, we have summarized all the emerging methodologies developed during 2016–2025 with an enduring description. This review will be very useful to synthetic/medicinal chemists, researchers of materials science, and in the catalysis domains.

2002年，夏普勒斯和梅尔达尔独立提出了名为“点击化学”（Click Chemistry）的突破性概念。该反应涉及Cu(I)催化的Huisgen型1,3-偶极环加成，即铜催化叠氮-炔环加成（CuAAC）的出现，以区域选择性的方式生成1,4-二取代1,2,3三唑。后来又采用了Ni、Rh、Ir、Zn、Ag等金属，并发展了电化学法和热法等非金属途径进行叠氮化物-炔环加成反应。点击化学促进化学反应，使两个物种以一种简单和选择性的方式连接，在温和的条件下很少或没有副产品。该反应在多个工业中的广泛应用使其成为一个蓬勃发展的研究领域。由于三唑键作为肽模拟物的特性，这种化学反应也有利于生物偶联和肽连接。在此，我们总结了2016-2025年期间开发的所有新兴方法，并进行了持久的描述。本文对合成/药物化学家、材料科学和催化领域的研究人员有一定的参考价值。

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引用次数: 0

β-formyl-β-nitroenamine: A user-friendly synthetic tool with versatile reactivities β-甲酰基-β-硝基胺：一个用户友好的合成工具，具有多种反应性

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-19 DOI: 10.1016/j.tet.2025.135056

Nagatoshi Nishiwaki

β-Formyl-β-nitroenamine (FNE), which possesses multiple functionalities, including formyl, amino, and nitro groups, in addition to a CC double bond with biased electron density, exhibits versatile reactivities. The two electrophilic sites react with dinucleophiles to afford nitro-substituted heterocycles. When the nucleophilic amino group and the electrophilic formyl group are reacted, polyfunctionalized pyridines are readily synthesized upon treatment with active methylene compounds. In addition, the biased electron density of the FNE molecule facilitates [4 + 2] or [4 + 4] cycloaddition. FNE is soluble in most organic solvents, is nonexplosive, and can be safely handled. Products with both electron-donating and electron-withdrawing groups are obtained; therefore, the push–pull property of FNE is transcribed to the product. These compounds play a crucial role in the development of optical and electronic materials, giving FNE exceptionally high synthetic utility.

β-甲酰基-β-硝基胺（FNE）具有多种官能团，包括甲酰基、氨基和硝基，除了具有偏电子密度的CC双键外，还具有多种反应活性。两个亲电位点与亲核试剂反应生成硝基取代杂环。当亲核氨基和亲电甲酰基反应时，经活性亚甲基化合物处理，容易合成多官能化吡啶。此外，FNE分子的偏置电子密度有利于[4 + 2]或[4 + 4]环加成。FNE可溶于大多数有机溶剂，无爆炸性，可安全处理。得到了既有给电子基团又有吸电子基团的产物；因此，FNE的推拉特性被转录到产物上。这些化合物在光学和电子材料的发展中起着至关重要的作用，使FNE具有极高的合成用途。

引用次数: 0

Design, synthesis, and pharmacological profiling of benzimidazole-based isoniazid analogues: A comprehensive investigation into antitubercular activity, molecular characterization, and computational study 苯并咪唑类异烟肼类似物的设计、合成和药理学分析：抗结核活性、分子表征和计算研究的综合研究

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-19 DOI: 10.1016/j.tet.2025.135066

Mahesh Vasava , Riya Khandelwal , Chintan Parmar , Shital Thacker , Dhanji P. Rajani , Hitesh D. Patel

In the present study, a series of novel N'-(2-(2-phenyl-1H-benzo[d]imidazole-1-yl)acetyl)isonicotinohydrazide (5a-p) and N'-(2-(1H-benzo[d]imidazole-1-yl)acetyl)isonicotinohydrazide (5'a-d) compounds were synthesized and evaluated for their pharmacological activities, including antibacterial, antitubercular, MDR-TB, and antioxidant properties. The synthesis involved the condensation of ethyl 2-(1H-benzo[d]imidazole-1-yl)acetate (4a-p and 4'a-d) with nicotinic hydrazide. Comprehensive structural analyses, including ¹H NMR, ¹³C NMR, IR, mass spectrometry, and CHN analyses, confirmed the formation of the newly synthesized compounds. The in vitro biological activity assessment revealed that certain compounds exhibited notable activity, as evidenced by their lowest MICs. Additionally, an in-silico computational study was conducted to evaluate the Absorption, Distribution, Metabolism, and Excretion (ADME) pharmacokinetic properties of the compounds. Molecular docking studies against the enoyl-ACP reductase enzyme, utilizing two different Protein Data Bank structures (PDBs: 4TZK and 4TZT), were performed. Moreover, a molecular dynamics study was undertaken to assess the stability of the ligand (5g)-receptor (4TZK) complex. Our findings suggested that these synthesized derivatives have the potential to serve as promising lead molecules for the development of effective antitubercular agents in the future.

本研究合成了一系列新的N'-（2-（2-苯基- 1h -苯并咪唑-1-基）乙酰基）异烟碱肼（5a-p）和N'-（2-（1h -苯并咪唑-1-基）乙酰基）异烟碱肼（5'a-d）化合物，并对其抗菌、抗结核、耐多药结核和抗氧化等药理活性进行了评价。该合成是由2-（1h -苯并[d]咪唑-1-基）乙酸乙酯（4a-p和4'a-d）与烟酰肼缩合而成。综合结构分析，包括1H NMR、13C NMR、IR、质谱分析和CHN分析，证实了新合成化合物的形成。体外生物活性评估显示，某些化合物具有显著的活性，其最低mic证明了这一点。此外，还进行了计算机计算研究，以评估化合物的吸收、分布、代谢和排泄（ADME）药代动力学特性。利用两种不同的蛋白质数据库结构（PDBs: 4TZK和4TZT），对烯酰acp还原酶进行了分子对接研究。此外，还进行了分子动力学研究，以评估配体(5g)-受体（4TZK）复合物的稳定性。我们的研究结果表明，这些合成的衍生物有潜力作为未来开发有效抗结核药物的有希望的先导分子。

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Synthesis of the β-d-mannose containing tetrasaccharide repeating unit corresponding to the O-specific polysaccharide of Salmonella cerro O:18 含四糖重复单元的β-d-甘露糖的合成与沙门氏菌O特异性多糖对应

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-11-15 DOI: 10.1016/j.tet.2025.135065

Aniket Majhi, Samim Sahaji, Anup Kumar Misra

A straightforward synthetic strategy has been developed for the synthesis of the tetrasaccharide containing a β-d-mannose moiety corresponding to the O-specific polysaccharide of Salmonella cerro (S. cerro) O:18 strain. The synthetic strategy involves 1,2-cis glycosylation of a d-mannose unit by H-bond mediated aglycone delivery using judiciously functionalized d-mannose thioglycoside donor. The glycosylation steps were high yielding with satisfactory stereochemistry at the glycosyl linkages.

采用一种简单的合成策略，合成了含有β-d-甘露糖片段的四糖，该四糖片段与沙门氏菌cerro (S. cerro) O:18菌株的O特异性多糖相对应。该合成策略包括利用合理功能化的d-甘露糖硫苷供体，通过氢键介导的苷元传递，将d-甘露糖单元1,2-顺式糖基化。糖基化步骤产率高，在糖基键上具有令人满意的立体化学性质。

引用次数: 0

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