Tetrahedron Letters最新文献

英文中文

Synthesis of (bicyclo[2.2.0]hex-1-yl)methanal and Arrhenius parameters for thermal rearrangement: Radical stabilizing effect of aldehyde substituents on highly strained CC bonds (bicyclo[2.2.0]hex-1-yl)methanal 的合成和热重排的 Arrhenius 参数：醛取代基对高应变 CC 键的辐射稳定作用

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-13 DOI: 10.1016/j.tetlet.2024.155369

Anita Nowienski , Murray G. Rosenberg , Udo H. Brinker

Bicyclo[2.2.0]hexane rearranges to hexa-1,5-diene via the cyclohexane-1,4-diyl diradical. The 1-formyl substituted derivative was sought to evaluate the effect of a CHO-group on the rate of rearrangement. (Bicyclo[2.2.0]hex-1-yl)methanal was prepared for the first time in a multistep synthesis starting from hexachlorocyclopentadiene. The pivotal last step was achieved by Swern oxidation of (bicyclo[2.2.0]hex-1-yl)methanol at T = –60 °C. The carbon skeleton of the alcohol precursor remains intact under those conditions. Thermolysis of the aldehyde to 2-methylenehex-5-enal follows a first-order rate law between T = 322.85–361.51 K (T_avg = 343.30 K). Seven rate constants k_T were used to plot log k_T vs. 1/T, which provided the Arrhenius parameters for the rearrangement: activation energy (E_a) = 25.4 ± 1.0 kcal/mol and pre-exponential factor (A₃₄₃) = 1.66 × 10¹² s⁻¹. The E_a is 10.6 kcal/mol below that of the unsubstituted archetype bicyclo[2.2.0]hexane. This sizable change in E_a reflects the radical stabilization energy of the CHO-group in 1-formylcyclohexane-1,4-diyl.

双环[2.2.0]己烷通过环己烷-1,4-二基二拉环重新排列为六-1,5-二烯。为了评估 CHO 基团对重排速率的影响，我们寻找了 1-甲酰基取代的衍生物。(以六氯环戊二烯为起点，通过多步合成法首次制备了（双环[2.2.0]己-1-基）甲醛。关键的最后一步是在 T = -60 °C 下通过 Swern 氧化 (双环[2.2.0]己-1-基)甲醇实现的。在这些条件下，醇前体的碳骨架保持完好。在 T = 322.85-361.51 K（Tavg = 343.30 K）之间，醛热解生成 2-亚甲基己-5-烯醛遵循一阶速率定律。利用七个速率常数 kT 绘制对数 kT 与 1/T 的关系图，得出了重排的阿伦尼乌斯参数：活化能 (Ea) = 25.4 ± 1.0 kcal/mol 和预指数因子 (A343) = 1.66 × 1012 s-1。Ea 比未取代的原型双环[2.2.0]己烷的 Ea 低 10.6 千卡/摩尔。Ea 的这一显著变化反映了 1-甲酰基环己烷-1,4-二基中 CHO 基团的自由基稳定能。

{"title":"Synthesis of (bicyclo[2.2.0]hex-1-yl)methanal and Arrhenius parameters for thermal rearrangement: Radical stabilizing effect of aldehyde substituents on highly strained CC bonds","authors":"Anita Nowienski , Murray G. Rosenberg , Udo H. Brinker","doi":"10.1016/j.tetlet.2024.155369","DOIUrl":"10.1016/j.tetlet.2024.155369","url":null,"abstract":"<div><div>Bicyclo[2.2.0]hexane rearranges to hexa-1,5-diene via the cyclohexane-1,4-diyl diradical. The 1-formyl substituted derivative was sought to evaluate the effect of a CHO-group on the rate of rearrangement. (Bicyclo[2.2.0]hex-1-yl)methanal was prepared for the first time in a multistep synthesis starting from hexachlorocyclopentadiene. The pivotal last step was achieved by Swern oxidation of (bicyclo[2.2.0]hex-1-yl)methanol at <em>T</em> = –60 °C. The carbon skeleton of the alcohol precursor remains intact under those conditions. Thermolysis of the aldehyde to 2-methylenehex-5-enal follows a first-order rate law between <em>T</em> = 322.85–361.51 K (<em>T</em><sub>avg</sub> = 343.30 K). Seven rate constants <em>k<sub>T</sub></em> were used to plot log <em>k<sub>T</sub></em> vs. 1/<em>T</em>, which provided the Arrhenius parameters for the rearrangement: activation energy (<em>E</em><sub>a</sub>) = 25.4 ± 1.0 kcal/mol and pre-exponential factor (<em>A</em><sub>343</sub>) = 1.66 × 10<sup>12</sup> s<sup>−1</sup>. The <em>E</em><sub>a</sub> is 10.6 kcal/mol below that of the unsubstituted archetype bicyclo[2.2.0]hexane. This sizable change in <em>E</em><sub>a</sub> reflects the radical stabilization energy of the CHO-group in 1-formylcyclohexane-1,4-diyl.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155369"},"PeriodicalIF":1.5,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699269","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Three new macrocarpene-type sesquiterpenes and three new ent-kaurane-type diterpenoids isolated from the styles and stigmas of Zea mays L. 从玉米花柱和柱头中分离出三种新的大果萜类倍半萜和三种新的ent-kaurane类二萜。

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-13 DOI: 10.1016/j.tetlet.2024.155359

Ming Zhao , Eryan Wu , Yini Yang , Liqiu Sun , Zhichun Shi , Yingnan Zhao , Jun Li , Dan Wang

Phytochemical investigation of the styles and stigmas of Zea mays L. led to the isolation of six new compounds, including three new macrocarpene-type sesquiterpenes, named zeaen A (1), zeaen B (2), zeaen C (3), and three new ent-kaurane-type diterpenoids, named zeamaysditerpen A (4), zeamaysditerpen B (5), zeamaysditerpen C (6). Their structures were elucidated by physical properties, 1D and 2D NMR, HR-ESI-TOF-MS, and other methods, alongside comparison with literature data. Furthermore, the chemotaxonomic significance of these compounds was also discussed.

通过对玉米花柱和柱头的植物化学研究，分离出了 6 个新化合物，包括 3 个新的大果萜类倍半萜，分别命名为玉米烯 A (1)、玉米烯 B (2)、玉米烯 C (3)；以及 3 个新的ent-kaurane 类二萜，分别命名为玉米二萜 A (4)、玉米二萜 B (5)、玉米二萜 C (6)。通过物理性质、一维和二维核磁共振、HR-ESI-TOF-MS 等方法以及与文献数据的对比，阐明了它们的结构。此外，还讨论了这些化合物的化学分类学意义。

引用次数: 0

Synthetic studies on fusicoccin A: Enantioselective synthesis of the C-ring fragment 夫西可辛 A 的合成研究：C 环片段的对映选择性合成

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-12 DOI: 10.1016/j.tetlet.2024.155364

Kanae Hayashi, Masahisa Nakada

The enantioselective synthesis of the C-ring fragment of fusicoccin A is described. The TBS ether of hydroxyketone prepared by baker’s yeast reduction was converted to the α-ethylidene ketone by aldol condensation with propionaldehyde, followed by Michael reaction with divinylcopper reagent and conversion to enol triflate to afford a single diastereomer. X-ray crystallographic analysis of the crystalline derivative of the single diastereomer showed that the asymmetric carbon formed by the Michael reaction was consistent with the configuration of the C15 asymmetric carbon of fusicoccin A. The vinyl group of the enol triflate was converted to a hydroxymethyl group by selective dihydroxylation with a bulky ligand, oxidative cleavage of the resultant 1,2-diol with lead tetraacetate, and DIBAL-H reduction. The hydroxymethyl group was subsequently converted to TBS ether, followed by the hydrogenolysis of the benzyl group and Dess–Martin oxidation, accomplishing the enantioselective synthesis of the desired C-ring fragment of fusicoccin A.

本文介绍了对映体选择性合成夫西可辛 A 的 C 环片段的方法。用面包酵母还原法制备的羟基酮的 TBS 醚通过与丙醛的醛醇缩合转化为 α-亚乙基酮，然后与二乙烯基铜试剂发生迈克尔反应并转化为三羟甲基烯醇，从而得到单一非对映异构体。对单一非对映异构体的晶体衍生物进行的 X 射线晶体分析表明，迈克尔反应形成的不对称碳与 fusicoccin A 的 C15 不对称碳的构型一致。羟甲基随后被转化为 TBS 醚，接着是苄基的氢解和 Dess-Martin 氧化，从而完成了所需的夫西可辛 A C 环片段的对映选择性合成。

引用次数: 0

Photochemical direct C3 cyanoalkylation of quinoxalin-2(1H)-ones with cyclobutanone oxime esters under catalyst-free conditions 无催化剂条件下喹喔啉-2(1H)-酮与环丁酮肟酯的光化学直接 C3 氰烷基化反应

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-12 DOI: 10.1016/j.tetlet.2024.155363

Jing Liu , Liting Liu , Zhiqi Lei , Xi Chen , Xia Zhao , Kui Lu

A photochemical direct C3 cyanoalkylation of quinoxalin-2(1H)-ones was achieved for the first time, using cyclobutanone oxime esters as cyanoalkyl precursors, without the need for a photocatalyst. The mild and environmentally friendly conditions make this protocol a valuable alternative for synthesizing C3 cyanoalkylated quinoxalin-2(1H)-ones.

利用环丁酮肟酯作为氰烷基前体，无需光催化剂，首次实现了喹喔啉-2(1H)-酮的光化学直接 C3 氰烷基化反应。该方法条件温和，对环境友好，是合成 C3 氰烷基喹喔啉-2(1H)-酮的重要替代方法。

引用次数: 0

Synthesis and evaluation of cyclic peptide-dasatinib conjugates as anti-melanoma agents 作为抗黑色素瘤药物的环肽-达沙替尼共轭物的合成与评估

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-10 DOI: 10.1016/j.tetlet.2024.155365

Shaban Darwish , Dorna Davani-Davari , Shirley Tong , Rakesh Kumar Tiwari , Sun Yang , Keykavous Parang

Herein, we synthesized two amphiphilic cyclic peptides, incorporating tryptophan and arginine residues, linked to dasatinib via a Cathepsin B-sensitive tetrapeptide (Gly-Phe-Leu-Gly). To mitigate steric hindrance and optimize drug release, we integrated two different linkers, succinate and glutarate, between the drug and peptide. The synthesis involved solid-phase techniques for the assembly of the peptide, followed by the coupling of the peptide on-resin with the linker, mild cleavage, and solution-phase cyclization. Conjugation of the peptide-attached linker with dasatinib was conducted in the presence of N-methylmorpholine and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), generating the novel prodrugs. The synthesized compounds were characterized by high-resolution mass spectrometry MALDI, and the purity was confirmed by analytical HPLC. The synthesized cyclic peptide-dasatinib conjugates containing glutarate and succinate linkers were further evaluated against human melanoma A375 cells, which exhibited IC₅₀ values of 4.2 μM and 8.8 μM, respectively. Variations in cytotoxicity could be attributed to linker properties affecting intracellular drug release or prodrug uptake.

在这里，我们合成了两种两亲性环肽，其中包含色氨酸和精氨酸残基，并通过对胰蛋白酶 B 敏感的四肽（Gly-Phe-Leu-Gly）与达沙替尼连接。为了减轻立体阻碍和优化药物释放，我们在药物和肽之间加入了两种不同的连接物--琥珀酸和戊二酸。合成过程采用固相技术组装多肽，然后将多肽在树脂上与连接体偶联，再进行温和的裂解和溶液相环化。在 N-甲基吗啉和 1-乙基-3-（3-二甲胺基丙基）碳二亚胺（EDC）存在下，将肽连接的连接体与达沙替尼共轭，生成新型原药。合成的化合物经高分辨率 MALDI 质谱鉴定，纯度经分析 HPLC 确认。合成的含有戊二酸和琥珀酸连接体的环肽-达沙替尼共轭物对人类黑色素瘤 A375 细胞进行了进一步评估，其 IC50 值分别为 4.2 μM 和 8.8 μM。细胞毒性的变化可能是由于连接体的特性影响了细胞内的药物释放或原药吸收。

{"title":"Synthesis and evaluation of cyclic peptide-dasatinib conjugates as anti-melanoma agents","authors":"Shaban Darwish , Dorna Davani-Davari , Shirley Tong , Rakesh Kumar Tiwari , Sun Yang , Keykavous Parang","doi":"10.1016/j.tetlet.2024.155365","DOIUrl":"10.1016/j.tetlet.2024.155365","url":null,"abstract":"<div><div>Herein, we synthesized two amphiphilic cyclic peptides, incorporating tryptophan and arginine residues, linked to dasatinib via a Cathepsin B-sensitive tetrapeptide (Gly-Phe-Leu-Gly). To mitigate steric hindrance and optimize drug release, we integrated two different linkers, succinate and glutarate, between the drug and peptide. The synthesis involved solid-phase techniques for the assembly of the peptide, followed by the coupling of the peptide on-resin with the linker, mild cleavage, and solution-phase cyclization. Conjugation of the peptide-attached linker with dasatinib was conducted in the presence of <em>N</em>-methylmorpholine and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), generating the novel prodrugs. The synthesized compounds were characterized by high-resolution mass spectrometry MALDI, and the purity was confirmed by analytical HPLC. The synthesized cyclic peptide-dasatinib conjugates containing glutarate and succinate linkers were further evaluated against human melanoma A375 cells, which exhibited IC<sub>50</sub> values of 4.2 μM and 8.8 μM, respectively. Variations in cytotoxicity could be attributed to linker properties affecting intracellular drug release or prodrug uptake.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155365"},"PeriodicalIF":1.5,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662342","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Formal synthesis of ferruginol methyl ether via an acid-catalysed intramolecular Diels–Alder cycloaddition 通过酸催化分子内 Diels-Alder 环加成正式合成阿魏精醇甲醚

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-08 DOI: 10.1016/j.tetlet.2024.155362

Mariana Macías Alonso , Lucía S. Andrés , Joaquín González Marrero

Aromatic abietane diterpenoids, known for their wide range of biological and pharmaceutical activities, have attracted considerable interest from synthetic and medicinal chemists. Although some aromatic abietane diterpenoids are naturally abundant, many are only available in limited quantities, constraining their use in detailed biological investigations. We initiated a project to synthesize these compounds, and as our first approach, we describe the formal synthesis of ferruginol methyl ether. Starting from tiglic aldehyde (6) and 2-bromo-5-methoxybenzoic acid (11), we synthesized the triene (3) in nine steps. The key transformation involved an acid-catalysed intramolecular Diels-Alder (IMDA) cyclisation of triene (3), leading to the formation of 12-methoxy-19-norpodocarpa-4(18),8,11,13-tetraene (14) as the primary product, with an overall yield of 17.3 % across ten steps. While the yield is modest, this approach provides a novel pathway for synthesizing abietane-type compounds. We are actively exploring strategies to improve the overall yield and developing an asymmetric synthesis variant.

芳香族双乙烷二萜以其广泛的生物和医药活性而闻名，引起了合成化学家和药物化学家的极大兴趣。虽然一些芳香族双乙烷二萜在自然界中含量丰富，但许多芳香族双乙烷二萜的数量有限，这限制了它们在详细生物学研究中的应用。我们启动了一个合成这些化合物的项目，作为我们的第一种方法，我们描述了铁杉醇甲醚的正式合成。从 Tiglic 醛（6）和 2-溴-5-甲氧基苯甲酸（11）开始，我们通过九个步骤合成了三烯（3）。关键的转化过程是在酸催化下对三烯（3）进行分子内 Diels-Alder (IMDA) 环化，生成 12-甲氧基-19-去甲二碳-4(18),8,11,13-四烯（14）作为主要产物，十个步骤的总收率为 17.3%。虽然收率不高，但这种方法为合成阿比坦类化合物提供了一条新途径。我们正在积极探索提高总产率和开发不对称合成变体的策略。

{"title":"Formal synthesis of ferruginol methyl ether via an acid-catalysed intramolecular Diels–Alder cycloaddition","authors":"Mariana Macías Alonso , Lucía S. Andrés , Joaquín González Marrero","doi":"10.1016/j.tetlet.2024.155362","DOIUrl":"10.1016/j.tetlet.2024.155362","url":null,"abstract":"<div><div>Aromatic abietane diterpenoids, known for their wide range of biological and pharmaceutical activities, have attracted considerable interest from synthetic and medicinal chemists. Although some aromatic abietane diterpenoids are naturally abundant, many are only available in limited quantities, constraining their use in detailed biological investigations. We initiated a project to synthesize these compounds, and as our first approach, we describe the formal synthesis of ferruginol methyl ether. Starting from tiglic aldehyde (<strong>6</strong>) and 2-bromo-5-methoxybenzoic acid (<strong>11</strong>), we synthesized the triene (<strong>3</strong>) in nine steps. The key transformation involved an acid-catalysed intramolecular Diels-Alder (IMDA) cyclisation of triene (<strong>3</strong>), leading to the formation of 12-methoxy-19-norpodocarpa-4(18),8,11,13-tetraene (<strong>14</strong>) as the primary product, with an overall yield of 17.3 % across ten steps. While the yield is modest, this approach provides a novel pathway for synthesizing abietane-type compounds. We are actively exploring strategies to improve the overall yield and developing an asymmetric synthesis variant.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155362"},"PeriodicalIF":1.5,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142656549","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of (2,3-dihydrobenzofuran-3-yl)acetic acids from salicylic aldehydes: Trimethylsilyl as traceless activating group 从水杨醛合成 (2,3-二氢苯并呋喃-3-基)乙酸：三甲基硅作为无踪活化基团

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-08 DOI: 10.1016/j.tetlet.2024.155354

Evgeny M. Buev, Polina A. Khardina, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh

Salicylic aldehydes were readily alkylated with (chloromethyl)trimethylsilane to give the silylated ortho-methoxy benzaldehydes in 85–96 % yields. These aldehydes were converted into arylidenemalonates in excellent yields. O-(Trimethylsilyl)methyl group was applied as the synthetic equivalent of aryloxymethyl anion in the nucleophilic cyclization at the alkene moiety promoted by cesium fluoride in DMF at 140 °C. In this way, (2,3-dihydrobenzofuran-3-yl)acetic acids and the corresponding esters were synthesized from salicylic aldehydes in 41–70 % overall yields.

水杨醛很容易与（氯甲基）三甲基硅烷发生烷基化反应，从而得到硅烷化的邻甲氧基苯甲醛，收率为 85-96%。这些醛以极高的收率转化为亚芳基丙二酸酯。在 140 °C 的 DMF 溶液中，在氟化铯的促进下，O-(三甲基硅烷基)甲基被用作芳氧基甲基阴离子的合成等价物，在烯分子上发生亲核环化反应。通过这种方法，以水杨醛为原料合成了（2,3-二氢苯并呋喃-3-基）乙酸和相应的酯，总产率为 41-70%。

引用次数: 0

Development of a simple and safe route to C-3 arylated 1H-pyrazoles 开发 C-3 芳基化 1H 吡唑的简单安全路线

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-08 DOI: 10.1016/j.tetlet.2024.155356

Dengke Li

A simple transition-metal-free and highly chemoselective strategy for the preparation of C-3 arylated 1H-pyrazoles with enaminones and p-toluenesulfonyl hydrazide (TsNHNH₂) has been developed. The current environmental benign protocols showed that, TsNHNH₂ could be served as the safe and easy-to-handle hydrazide for the preparation of C-3 arylated 1H-pyrazoles instead of the explosive and genotoxic hydrazine hydrate under mild conditions, with broad substrate scope and excellent functional group tolerance. More importantly, a gram-scale synthesis of a synthetic equivalent of key intermediate to immuno-oncology agonist BMS-986299 was demonstrated successfully through a simple crystallization or extraction process for the scalable production.

利用烯酮和对甲苯磺酸酰肼（TsNHNH2）制备 C-3 芳基化 1H 吡唑的简单无过渡金属和高化学选择性策略已经开发出来。目前的环境友好方案表明，TsNHNH2 可作为安全、易于处理的酰肼，在温和条件下代替具有爆炸性和遗传毒性的水合肼制备 C-3 芳基化 1H-吡唑，具有广泛的底物范围和优异的官能团耐受性。更重要的是，通过简单的结晶或萃取工艺，成功合成了克级规模的免疫肿瘤激动剂 BMS-986299 的关键中间体。

引用次数: 0

Zincke reaction in the synthesis of novel glutaconaldehyde derivatives: Synthesis of potassium 2,10-diamino-1,1,3,9,11,11-hexacyanoundeca-2,4,6,8,10-pentaen-1-ide and its application for fluorimetric quantitative determination of Fe3+ ions 合成新型戊二醛衍生物中的锌克反应：2,10- 二氨基-1,1,3,9,11,11-六氰基戊-2,4,6,8,10-五烯-1-酰胺钾的合成及其在荧光法定量测定 Fe3+ 离子中的应用

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-08 DOI: 10.1016/j.tetlet.2024.155360

Sergey V. Karpov, Yakov S. Kaukov, Alexey V. Eremkin, Oleg E. Nasakin

Under the conditions of a modified “one-pot” Zincke reaction, novel aza-merocyanines based on the dimer of malononitrile, pyridine, and α-iodonicotinonitrile derivatives were synthesized. It was demonstrated that in the presence of weak bases, the solutions of the obtained compounds exhibit fluorescence with λ_max^em around 660 nm, accompanied by a color change from pale yellow to violet. Interaction of these aza-merocyanines with the potassium salt of the malononitrile dimer yielded a new glutaconaldehyde derivative, which can be used for the quantitative fluorimetric determination of Fe³⁺ ions at low concentrations.

在改进的 "一锅式 "锌克反应条件下，合成了基于丙二腈、吡啶和 α-iodonicotinonitrile 衍生物二聚体的新型偶氮猩红素。实验证明，在弱碱存在的情况下，所得化合物的溶液会发出 λmaxem 波长约为 660 纳米的荧光，同时颜色也会从淡黄色变为紫色。这些偶氮络氨酸与丙二腈二聚体的钾盐相互作用，产生了一种新的戊二醛衍生物，可用于低浓度下 Fe3+ 离子的荧光定量测定。

引用次数: 0

Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines 使用 CS2 和环氧胺合成 1,3-噻唑烷-2-硫醚

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2024-11-06 DOI: 10.1016/j.tetlet.2024.155361

Azim Ziyaei Halimehjani , Farzaneh Noorakhtar , Zahra Marjani

An efficient method for the synthesis of 5-(hydoxymethyl)-1,3-thiazolidine-2-thiones is developed via the reaction of carbon disulfide with N-alkyl(aryl) epoxy amines. The reaction proceeds via intramolecular epoxide ring opening with in situ prepared dithiocarbamic acid. The products were obtained in good to high yields.

通过二硫化碳与 N-烷基（芳基）环氧胺的反应，开发出一种合成 5-（水氧甲基）-1,3-噻唑烷-2-硫代化合物的高效方法。该反应通过分子内环氧化物开环与原位制备的二硫代氨基甲酸进行。产物的收率很高。

引用次数: 0

首页上一页

下一页尾页

类型

全部化学•材料生命科学医学物理工程技术环境•农林材料科学地球科学法学管理学化学环境科学与生态学计算机科学教育学经济学农林科学人文科学生物学数学物理与天体物理心理学综合性期刊其他工业工程理学历史学农学文学信息工程

数据库

全部 ACS Publications Elsevier ieeexplore Springer The Royal Society of Chemistry Wiley

期刊

Tetrahedron Letters

全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.

﹀