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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
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
{"title":"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","authors":"Sergey V. Karpov,&nbsp;Yakov S. Kaukov,&nbsp;Alexey V. Eremkin,&nbsp;Oleg E. Nasakin","doi":"10.1016/j.tetlet.2024.155360","DOIUrl":"10.1016/j.tetlet.2024.155360","url":null,"abstract":"<div><div>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<sub>max</sub><sup>em</sup> 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 Fe<sup>3+</sup> ions at low concentrations.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155360"},"PeriodicalIF":1.5,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662324","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 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
Tetrahedron Letters Pub Date : 2024-11-06 DOI: 10.1016/j.tetlet.2024.155361
Azim Ziyaei Halimehjani , Farzaneh Noorakhtar , Zahra Marjani
{"title":"Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines","authors":"Azim Ziyaei Halimehjani ,&nbsp;Farzaneh Noorakhtar ,&nbsp;Zahra Marjani","doi":"10.1016/j.tetlet.2024.155361","DOIUrl":"10.1016/j.tetlet.2024.155361","url":null,"abstract":"<div><div>An efficient method for the synthesis of 5-(hydoxymethyl)-1,3-thiazolidine-2-thiones is developed <em>via</em> the reaction of carbon disulfide with <em>N</em>-alkyl(aryl) epoxy amines. The reaction proceeds via intramolecular epoxide ring opening with <em>in situ</em> prepared dithiocarbamic acid. The products were obtained in good to high yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155361"},"PeriodicalIF":1.5,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662341","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
One-pot multicomponent photo-induced eosin-Y catalyzed synthesis of 2-amino oxa/thiazine derivatives 单锅多组分光诱导曙红-Y 催化合成 2-氨基氧杂/噻嗪衍生物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-06 DOI: 10.1016/j.tetlet.2024.155339
Km Garima , Vishal Srivastava , Praveen P. Singh , Pravin K. Singh
{"title":"One-pot multicomponent photo-induced eosin-Y catalyzed synthesis of 2-amino oxa/thiazine derivatives","authors":"Km Garima ,&nbsp;Vishal Srivastava ,&nbsp;Praveen P. Singh ,&nbsp;Pravin K. Singh","doi":"10.1016/j.tetlet.2024.155339","DOIUrl":"10.1016/j.tetlet.2024.155339","url":null,"abstract":"<div><div>An effective and advantageous one-pot multicomponent photo-induced methodology has been developed for the synthesis of biologically potent 2-amino-4<em>H</em>-1,3-oxa/thiazine from substituted benzaldehyde, ethynylbenzene and urea/thiourea catalyzed by eosin-Y at room temperature using EtOH as a green solvent with wide range of applications in pharmaceutical and agriculture industries. This proposed work emphasizes to investigate an accessible, safe, easy and convenient method for the synthesis of 2-amino oxa/thiazine derivatives with good to excellent yield.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155339"},"PeriodicalIF":1.5,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592695","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
Controllable hydrogenation of arylacetylenes with NaBH4 catalyzed by palladium nanoparticles in a fixed-bed system 固定床系统中钯纳米颗粒催化的芳基乙炔与 NaBH4 的可控氢化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-05 DOI: 10.1016/j.tetlet.2024.155355
Wei Zhang, Guohao Wu, Ying Wang, Yanhua Zhang
{"title":"Controllable hydrogenation of arylacetylenes with NaBH4 catalyzed by palladium nanoparticles in a fixed-bed system","authors":"Wei Zhang,&nbsp;Guohao Wu,&nbsp;Ying Wang,&nbsp;Yanhua Zhang","doi":"10.1016/j.tetlet.2024.155355","DOIUrl":"10.1016/j.tetlet.2024.155355","url":null,"abstract":"<div><div>A continuous flow reactor packed with glass fiber-supported palladium nanoparticles (PdNPs/GF) is designed and successfully applied in the controllable hydrogenation of arylacetylenes with sodium borohydride (NaBH<sub>4</sub>) in methanol. By adjusting the flow rate, the substrate concentration and the amount of NaBH<sub>4</sub>, the selectivity of the products are tunable as desired. It is interesting that fully hydrogenated products (aryl alkanes) are obtained with up to 95 % yield at a flow rate of 1.5 mL/min with a substrate concentration of 5.0 mM and 3.0 eq. of NaBH<sub>4</sub>. On the other hand, the selective semi-hydrogenation transformation is much easier to achieve, and the yield of aryl olefins is up to 87 %. This fixed-bed system offers a simple and efficient method for the hydrogenation of arylacetylenes, which has great potential in the future scale-up syntheses.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155355"},"PeriodicalIF":1.5,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586185","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
Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response 设计和合成基于萘二甲酰亚胺的 CO 荧光探针，实现三色检测和开关响应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-03 DOI: 10.1016/j.tetlet.2024.155357
Junyu Zhang , Guoling Li , Xuguang Zhu, Huilong Xu, Zhonghai Ni, Yun Zhao
{"title":"Design and synthesis of naphthalimide-based CO fluorescent probes realizing tricolor detection and turn-on/off response","authors":"Junyu Zhang ,&nbsp;Guoling Li ,&nbsp;Xuguang Zhu,&nbsp;Huilong Xu,&nbsp;Zhonghai Ni,&nbsp;Yun Zhao","doi":"10.1016/j.tetlet.2024.155357","DOIUrl":"10.1016/j.tetlet.2024.155357","url":null,"abstract":"<div><div>Carbon monoxide (CO) fluorescent probes have attracted tremendous attention attributed to their low detection limit, high specificity, simple operation and good biocompatibility. However, the relationship between the molecular structure and the fluorescence response signal still needs to be systematically elucidated for different applications. Herein, three different CO fluorescent probes based on naphthalimide derivative with blue emission (B-NIA), green emission (G-NIA), and near-infrared emission (R-NIA) were designed and synthesized. Three-primary colors and opposite turn-on or turn-off fluorescent responses to CO were achieved by regulating the conjugation system of fluorophores and the position of fluorescent recognition group. The change of fluorescence response and sensing mechanism for CO detection was studied by theory calculation and mass spectrometry analysis. All the B/G/R-NIA possessed high sensitivity for CO detection. Notably, the R-NIA emerged with a noticeable NIR fluorescence response to CO with a low detection limit (0.61 µM) and high selectivity and relative pH stability. In addition, the R-NIA showed particularly low cytotoxicity and has been successfully used to detect CO in living cells. These studies provided the theoretical reference and technical route to synthesize fluorescent probes with different emission wavelengths and opposite fluorescent responses to CO for various application scenarios.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155357"},"PeriodicalIF":1.5,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142586186","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
Diastereoselective synthesis of novel alkaloid-like 1,2,3,3a,7b,12-hexahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrroles 新型生物碱样 1,2,3,3a,7b,12-六氢茚并[2′,1′:2,3]茚并[1,2-c]吡咯的非对映选择性合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-02 DOI: 10.1016/j.tetlet.2024.155358
Vladimir D. Fedorenko, Evgeny M. Buev, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh
{"title":"Diastereoselective synthesis of novel alkaloid-like 1,2,3,3a,7b,12-hexahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrroles","authors":"Vladimir D. Fedorenko,&nbsp;Evgeny M. Buev,&nbsp;Vladimir S. Moshkin,&nbsp;Vyacheslav Y. Sosnovskikh","doi":"10.1016/j.tetlet.2024.155358","DOIUrl":"10.1016/j.tetlet.2024.155358","url":null,"abstract":"<div><div>2-Arylideneindan-1,3-diones readily undergo [3+2]-cycloaddition with <em>N</em>-methylazomethine ylide derived from sarcosine and formaldehyde to give 4′-aryl-1′-methylspiro[indene-2,3′-pyrrolidine]-1,3-diones, which were further cyclized in perchloric acid to (3a<em>R*</em>,7b<em>R*</em>,12a<em>R*</em>)-7b-hydroxy-2-methyl-2,3,3a,7b-tetrahydroindeno[2′,1′:2,3]indeno[1,2-<em>c</em>]pyrrol-12(1<em>H</em>)-ones in 33–100 % yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155358"},"PeriodicalIF":1.5,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662321","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
DFT study on mechanism of nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides 镍催化下芳基氟化物与烷基溴的脱羰基还原烷基化机理的 DFT 研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-10-30 DOI: 10.1016/j.tetlet.2024.155353
Lijuan Liu, Zhenfeng Shang, Ruifang Li, Xiufang Xu
{"title":"DFT study on mechanism of nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides","authors":"Lijuan Liu,&nbsp;Zhenfeng Shang,&nbsp;Ruifang Li,&nbsp;Xiufang Xu","doi":"10.1016/j.tetlet.2024.155353","DOIUrl":"10.1016/j.tetlet.2024.155353","url":null,"abstract":"<div><div>The mechanism of the nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides is investigated using density functional theory calculations. The calculation result shows that the reaction mechanism involves sequential steps of C–F bond oxidative addition, decarbonylation, alkyl radical addition, C(sp<sup>2</sup>)–C(sp<sup>3</sup>) reductive elimination to afford the product, single electron transfer (SET) and reduction by Zn to regenerate the initiating complex. And the step of C–F bond oxidative addition was found to be the rate-determining step. The decarbonylation should occur before the alkyl radical addition. The effects of 1,3-bis(diphenylphosphino)propane (DPPP) ligand and different substrates on the reactivity were also analyzed. These calculation results disclosed the detailed reaction mechanism and shed lights on some ambiguous suggestions from experiments.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155353"},"PeriodicalIF":1.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662318","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
An environmentally friendly method for the synthesis of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines in water promoted by potassium, sodium and ammonium chlorides 一种在钾、钠和铵氯化物促进下在水中合成 1,2,3,4-四氢吡啶和六氢咪唑并[1,2-a]吡啶的环保型方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-10-30 DOI: 10.1016/j.tetlet.2024.155348
Natalia N. Gibadullina , Aigul R. Mukhamedyarova , Aleksandr N. Lobov , Yuri S. Zimin , Vladimir A. Dokichev
{"title":"An environmentally friendly method for the synthesis of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines in water promoted by potassium, sodium and ammonium chlorides","authors":"Natalia N. Gibadullina ,&nbsp;Aigul R. Mukhamedyarova ,&nbsp;Aleksandr N. Lobov ,&nbsp;Yuri S. Zimin ,&nbsp;Vladimir A. Dokichev","doi":"10.1016/j.tetlet.2024.155348","DOIUrl":"10.1016/j.tetlet.2024.155348","url":null,"abstract":"<div><div>A new one-pot method was developed for the synthesis of polyfunctional 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines by three-component reaction of ethyl 3-oxobutanoate with formaldehyde and primary amines occurring in water in the presence of electrolytes (NaCl, KCl, NH<sub>4</sub>Cl) at room temperature. This environmentally friendly method is highly atom economic, because the only by-products it gives are three water molecules. The effect of the structure of primary amines and reaction conditions on the degree of formation of 1,2,3,4-tetrahydropyridines and hexahydroimidazo[1,2-a]pyridines was investigated.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155348"},"PeriodicalIF":1.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142662320","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
Total synthesis of natural benzoazepinoquinolinone alkaloid irrepairzepine via Au(I)-catalyzed cycloisomerization and regioselective functionalization 通过金(I)催化的环异构化和区域选择性官能化全合成天然苯并氮杂卓喹啉酮生物碱伊瑞西平
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-10-28 DOI: 10.1016/j.tetlet.2024.155338
Jeonghwan Park , Sujin Lee , Young Taek Han
{"title":"Total synthesis of natural benzoazepinoquinolinone alkaloid irrepairzepine via Au(I)-catalyzed cycloisomerization and regioselective functionalization","authors":"Jeonghwan Park ,&nbsp;Sujin Lee ,&nbsp;Young Taek Han","doi":"10.1016/j.tetlet.2024.155338","DOIUrl":"10.1016/j.tetlet.2024.155338","url":null,"abstract":"<div><div>Irrepairzepine (<strong>1</strong>), a unique benzoazepinoquinolinone alkaloid isolated from an endophytic fungus, exhibits synthetic lethality targeting in PTEN-deficient glioblastoma cells. Herein, the first synthesis of irrepairzepine was achieved through a series of high-yielding reactions. The key steps include the synthesis of quinoline via the Au(I)-catalyzed cycloisomerization of <em>N</em>-propargyl aniline and construction of the azepinone core through the acid-catalyzed lactamization of an aminophenyl cyanoquinoline precursor, which was prepared using a simple umpolung approach that involves regioselective bromination followed by the Rosenmund-von Braun reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155338"},"PeriodicalIF":1.5,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578494","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
Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates 相转移催化的芳基乙酸酯的对映选择性 α-烷基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-10-28 DOI: 10.1016/j.tetlet.2024.155347
Yinuo Xiao, Zhenpeng Li, Changming Xu
{"title":"Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates","authors":"Yinuo Xiao,&nbsp;Zhenpeng Li,&nbsp;Changming Xu","doi":"10.1016/j.tetlet.2024.155347","DOIUrl":"10.1016/j.tetlet.2024.155347","url":null,"abstract":"<div><div>A chiral spirocyclic quaternary ammonium salt catalyzed asymmetric alkylation, especially methylation, of α-aryl esters possessing inherently poor reactivity under strong basic conditions has been developed, giving the target products with up to 94 % ee. This mild process was also applied to synthesize optically pure naproxen.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155347"},"PeriodicalIF":1.5,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142552888","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
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