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Ir(III)-catalyzed C–H alkenylation/annulation of N-iminopyridinium ylides with acrylates and alkynes Ir(III)催化的 N-亚氨基吡啶鎓酰化物与丙烯酸酯和炔烃的 C-H 烯化/annulation 反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-22 DOI: 10.1016/j.tet.2024.134322
Xiaopei Chen , Zhiwei Ma , Chuanchuan Wang, Xuehui Hou, Juntao Liu
{"title":"Ir(III)-catalyzed C–H alkenylation/annulation of N-iminopyridinium ylides with acrylates and alkynes","authors":"Xiaopei Chen ,&nbsp;Zhiwei Ma ,&nbsp;Chuanchuan Wang,&nbsp;Xuehui Hou,&nbsp;Juntao Liu","doi":"10.1016/j.tet.2024.134322","DOIUrl":"10.1016/j.tet.2024.134322","url":null,"abstract":"<div><div>A facile and efficient protocol for Ir(III)-catalyzed ortho-alkenylation and annulation of N-iminopyridinium ylides with acrylates and alkynes has been developed, providing o-alkenyl benzamides and isoquinolones in good to excellent yields. This reaction proceeds well under external oxidant free conditions with high practicality and efficiency, and broad functional group tolerance.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134322"},"PeriodicalIF":2.1,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533901","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
A smartphone-assisted chromogenic and fluorogenic dual-channel sensor for specific determination of toxic Pb2+ ions with multifaceted applications 用于特异性测定有毒 Pb2+ 离子的智能手机辅助显色和荧光双通道传感器的多方面应用
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-21 DOI: 10.1016/j.tet.2024.134316
Haiyan Xu , Wenlong Qin , Junyu Zhu , Ying-Guo Liu
{"title":"A smartphone-assisted chromogenic and fluorogenic dual-channel sensor for specific determination of toxic Pb2+ ions with multifaceted applications","authors":"Haiyan Xu ,&nbsp;Wenlong Qin ,&nbsp;Junyu Zhu ,&nbsp;Ying-Guo Liu","doi":"10.1016/j.tet.2024.134316","DOIUrl":"10.1016/j.tet.2024.134316","url":null,"abstract":"<div><div>Heavy metal pollutants, such as Pb<sup>2+</sup> ions, pose a substantial hazard to human health and ecosystems, and it was of great significance to develop cost-effective and portable techniques for online and visual detection of Pb<sup>2+</sup>. Herein, we fabricated a novel chromogenic and fluorogenic dual-channel sensor <strong>NQA</strong> through a Schiff base reaction involving a dicyanoisophorone derivative and isoniazid, enabling effective detection of Pb<sup>2+</sup> ions. Upon complexation with Pb<sup>2+</sup> ions at a 1:1 M ratio, the fluorescence intensity of <strong>NQA</strong> exhibited a remarkable enhancement. The naked-eye colorimetric detection utilizing <strong>NQA</strong> demonstrated a distinct color change to specific Pb<sup>2+</sup> ions concentration from yellow to light pink. Based on this principle, a smartphone-assisted sensing platform was developed for visual and high-quality identification of Pb<sup>2+</sup> in real samples. The UV binding constant for Pb<sup>2+</sup> ions was determined to be 1.84 × 10<sup>5</sup> M<sup>−1</sup>, with a detection limit of 0.38 μM. Furthermore, the versatility of <strong>NQA</strong> extended to applications in naked-eye test paper experiments, the detection of Pb<sup>2+</sup> ions in real water samples and living cells, showcasing its potential for environmental and biological monitoring.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134316"},"PeriodicalIF":2.1,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533897","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Electro-promoted radical-radical cross-coupling reaction to synthesize sulfonamides 电促进自由基-自由基交叉偶联反应合成磺胺类药物
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-20 DOI: 10.1016/j.tet.2024.134315
Hang Gong , Hongmei Fu , Chao Lu , Changqun Cai
{"title":"Electro-promoted radical-radical cross-coupling reaction to synthesize sulfonamides","authors":"Hang Gong ,&nbsp;Hongmei Fu ,&nbsp;Chao Lu ,&nbsp;Changqun Cai","doi":"10.1016/j.tet.2024.134315","DOIUrl":"10.1016/j.tet.2024.134315","url":null,"abstract":"<div><div>An electrochemical decarbonylation of DMF to achieve <em>N,N</em>-dimethyl amino radical and denitrification of sulfonyl hydrazide to achieve sulfonyl radical in the absence of transition metal and additional oxidant was reported here. Signifyingly, cross-coupling reaction rather than homocoupling reactions completely prevail in competition to obtain sulfonamides, which usually exist as skeletons of pharmaceuticals. This work provides a new method for cracking DMF into <em>N,N</em>-dimethylamino radical, and found a value-added application of this industrialized bulk chemical to the synthesis of sulfonamides.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134315"},"PeriodicalIF":2.1,"publicationDate":"2024-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533892","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Steroid-based hydrazones as anabolic agents: Design, synthesis, computational studies, and biological evaluation in human skeletal muscle cell line 作为同化制剂的类固醇酰肼：设计、合成、计算研究以及在人类骨骼肌细胞系中的生物学评估
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-19 DOI: 10.1016/j.tet.2024.134305
Fermín Flores-Manuel , Gabriel Guerrero-Luna , Israel Quiroga-Montes , Kenia Salvador-Atonal , Amairani Domínguez-Bahena , Maura Cárdenas-García , María Guadalupe Hernández-Linares
{"title":"Steroid-based hydrazones as anabolic agents: Design, synthesis, computational studies, and biological evaluation in human skeletal muscle cell line","authors":"Fermín Flores-Manuel ,&nbsp;Gabriel Guerrero-Luna ,&nbsp;Israel Quiroga-Montes ,&nbsp;Kenia Salvador-Atonal ,&nbsp;Amairani Domínguez-Bahena ,&nbsp;Maura Cárdenas-García ,&nbsp;María Guadalupe Hernández-Linares","doi":"10.1016/j.tet.2024.134305","DOIUrl":"10.1016/j.tet.2024.134305","url":null,"abstract":"<div><div>Hydrazone derivatives were synthesized in a three-step process starting from diosgenin and then tested for their anabolic activity. Through <em>in silico</em> analysis, we identified proteins associated with muscle growth to elucidate the plausible mechanisms and interactions between these compounds and the active site amino acids, thereby providing a rationale for the observed biological results. The results of the <em>in vitro</em> assay on the human skeletal muscle cell line showed an increase in the number of viable cells, which was determined using increasing concentrations of each compound through the XTT assay. Additionally, the increase in protein concentration was measured using the Bradford method. The experimental evaluation revealed that all compounds have differences in increased protein/cell percentage compared to the control and testosterone, which suggests a hyperplastic/hypertrophic effect with a normal morphology.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134305"},"PeriodicalIF":2.1,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533201","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Transition metal-catalyzed olefination of alkyl heteroarenes with alcohols 过渡金属催化烷基杂环戊烯与醇的烯化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-18 DOI: 10.1016/j.tet.2024.134306
Bin Guo , Jing Zhang , Dan Chen , David J. Young , Hong-Xi Li
{"title":"Transition metal-catalyzed olefination of alkyl heteroarenes with alcohols","authors":"Bin Guo ,&nbsp;Jing Zhang ,&nbsp;Dan Chen ,&nbsp;David J. Young ,&nbsp;Hong-Xi Li","doi":"10.1016/j.tet.2024.134306","DOIUrl":"10.1016/j.tet.2024.134306","url":null,"abstract":"<div><div>Transition metal catalyzed direct olefination of alkyl heteroarenes with alcohols using acceptorless dehydrogenative coupling (ADC) reactions and aerobic oxidative olefination are effective, versatile transformations for the construction of alkenyl heterocyclic compounds. Various transition metal catalysts based on noble metals (Ru) and their earth-abundant equivalents (Mn, Ni, Fe, Co) have been employed for these protocols. Water and hydrogen are the only byproducts and the starting alcohols are less toxic, more readily available, more easily handled and more atom economical than their halogen counterparts. This review details recent advances in these green methodologies, describing scope, reaction mechanisms, chemo-selectivity and applications in synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134306"},"PeriodicalIF":2.1,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533202","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
1,5-Disubstituted-1,2,3-Triazoles as GABA analogues: Synthesis, QSAR and biological evaluation as Pseudomonas fluorescens GABA-AT inhibitors 作为 GABA 类似物的 1,5-二取代-1,2,3-三唑：作为荧光假单胞菌 GABA-AT 抑制剂的合成、QSAR 和生物学评价
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-18 DOI: 10.1016/j.tet.2024.134300
Lucero Díaz-Peralta , Mario Fernandez-Zertuche , Juan Alberto Guevara-Salazar , Jessica R. Moran-Diaz , Luis Eduardo Hernandez-Dominguez , Rodrigo Said Razo-Hernández
{"title":"1,5-Disubstituted-1,2,3-Triazoles as GABA analogues: Synthesis, QSAR and biological evaluation as Pseudomonas fluorescens GABA-AT inhibitors","authors":"Lucero Díaz-Peralta ,&nbsp;Mario Fernandez-Zertuche ,&nbsp;Juan Alberto Guevara-Salazar ,&nbsp;Jessica R. Moran-Diaz ,&nbsp;Luis Eduardo Hernandez-Dominguez ,&nbsp;Rodrigo Said Razo-Hernández","doi":"10.1016/j.tet.2024.134300","DOIUrl":"10.1016/j.tet.2024.134300","url":null,"abstract":"<div><div>We report the synthesis of a new series of γ-aminobutyric acid (GABA) analogues as possible GABA-AT inhibitors, where the nitrogen at the Ƴ-position is contained in a 1,5-disubstituted-1,2,3-triazole ring system. The triazole ring system was assembled by the Ru(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (RuACC) protocol. GABA-AT inhibition activity was predicted by means of a QSAR model that was constructed in this work. Different molecular descriptors families were employed for its construction, like steric type (<span><math><mrow><mi>W</mi><mi>a</mi><mi>p</mi></mrow></math></span> and <span><math><mrow><mi>P</mi><mi>W</mi><mn>5</mn></mrow></math></span>), solubility type (<span><math><mrow><mo>Δ</mo><mtext>PSA</mtext></mrow></math></span>), and electronic type (<span><math><mrow><mo>Δ</mo><msub><mrow><mi>T</mi><mi>r</mi><mi>i</mi><mi>a</mi><mi>z</mi><mi>o</mi><mi>l</mi><mi>e</mi></mrow><mn>3</mn></msub></mrow></math></span>). Additionally, a similarity analysis based on the electronic profile of 1,5-triazole and 1,4-triazole GABA analogues was done to support the QSAR predictions. Finally, the three best candidates were biologically tested as <em>Pseudomonas fluorescens</em> GABA-AT inhibitors showing an inhibition percent compared to FDA approved inhibitors.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134300"},"PeriodicalIF":2.1,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142533203","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Assembling phthalaldehyde and o-aminochalcones by Pd(II) catalyzed tandem reaction for synthesizing isoindoloindonole fluorophores 通过钯(II)催化串联反应组装邻苯二甲醛和邻氨基查耳酮以合成异吲哚吲哚荧光团
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-11 DOI: 10.1016/j.tet.2024.134302
Arunava Misra, Mohabul Alam Mondal
{"title":"Assembling phthalaldehyde and o-aminochalcones by Pd(II) catalyzed tandem reaction for synthesizing isoindoloindonole fluorophores","authors":"Arunava Misra,&nbsp;Mohabul Alam Mondal","doi":"10.1016/j.tet.2024.134302","DOIUrl":"10.1016/j.tet.2024.134302","url":null,"abstract":"<div><div>One-pot synthesis of isoindoloindonoles having various auxochrome, from easily available starting materials phthalaldehyde and <em>o</em>-aminochalcone, involving palladium(II) acetate catalysis in acetic acid is reported. A mechanism based on the formation of 2-aryl-2<em>H</em>-isoindol-1-ol (<strong>22</strong>) intermediate is proposed for the formation of the tetracyclic core of isoindoloindonoles. The possible intramolecular cyclization via the direct participation of the carbonyl vs the adjacent αβ-conjugated double bond was evaluated. Thus, a detailed study on how the presence of electronically different groups at the β position of chalcones affects the outcome of the cyclization reaction and the photophysical properties of the resulting isoindoloindolones is presented here. Furthermore, the core structure was determined using NMR, mass and single-crystal X-ray diffraction analysis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134302"},"PeriodicalIF":2.1,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142433603","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Visible-light-mediated cyclopropanation reactions of 3-diazooxindoles with olefins 可见光介导的 3-重氮氧化吲哚与烯烃的环丙烷化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-11 DOI: 10.1016/j.tet.2024.134296
Zhuangzhuang Mu, Haochi Xie, Shundong Gan, Hujin Li, Yanan Hou, Mingcheng Qian, Shuai Zhao, Xin Chen
{"title":"Visible-light-mediated cyclopropanation reactions of 3-diazooxindoles with olefins","authors":"Zhuangzhuang Mu,&nbsp;Haochi Xie,&nbsp;Shundong Gan,&nbsp;Hujin Li,&nbsp;Yanan Hou,&nbsp;Mingcheng Qian,&nbsp;Shuai Zhao,&nbsp;Xin Chen","doi":"10.1016/j.tet.2024.134296","DOIUrl":"10.1016/j.tet.2024.134296","url":null,"abstract":"<div><div>Visible-light-mediated metal-free cyclopropanation reaction of diazo compounds with different olefins or arenes have been fully developed in recent years. However, electron-deficient olefins still could not be well tolerated in these reactions. Here, by using 3-diazooxindole as the carbene precursor, the visible-light-mediated cyclopropanation reaction of diazo compounds with electron-deficient olefins was successfully developed. The electron-rich olefins were also well tolerated in the reactions. A series of spirocyclopropyloxindoles were synthesized in moderate to high yields under mild, metal-free conditions. Mechanism studies reveal that both singlet and triplet carbenes are probably involved in the reaction.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134296"},"PeriodicalIF":2.1,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142433604","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Visible-light-promoted one-pot synthesis of β-keto sulfones from aryldiazo tetrafluoroborate salts via aerobic multicomponent reaction 通过有氧多组分反应，以芳基重氮四氟硼酸盐为原料，在可见光促进下一步合成β-酮砜
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-10 DOI: 10.1016/j.tet.2024.134303
Truong Giang Luu , Hee-Kwon Kim
{"title":"Visible-light-promoted one-pot synthesis of β-keto sulfones from aryldiazo tetrafluoroborate salts via aerobic multicomponent reaction","authors":"Truong Giang Luu ,&nbsp;Hee-Kwon Kim","doi":"10.1016/j.tet.2024.134303","DOIUrl":"10.1016/j.tet.2024.134303","url":null,"abstract":"<div><div>β-Keto sulfone is a useful structure in organic chemistry and pharmaceuticals. In the present study, we developed a highly efficient visible-light-promoted reaction to prepare β-keto sulfones under mild conditions. Synthesis was achieved via one-pot multi-component reaction of aryldiazo tetrafluoroborate salts, alkenes, and DABSO in the presence of air (O<sub>2</sub>) with rhodamine B serving as the photocatalyst. A variety of β-keto sulfones were obtained at high yields by this one-pot operation under aerobic atmosphere. This oxysulfonylation procedure has benefits such as mild reaction conditions, a wide tolerance of functional groups, and simplicity, making it a promising choice for preparing valuable β-keto sulfones.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134303"},"PeriodicalIF":2.1,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142433602","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Attempted synthesis of the central 2,2-disubstituted pseudoindoxyl core of Austamide via a [Au]-catalyzed nitroalkyne cycloisomerization and intramolecular [3 + 2]-cycloaddition 通过[Au]催化的硝基炔环异构化和分子内[3 + 2]-环加成尝试合成奥斯特酰胺的中心 2,2-二取代假吲哚核心
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-10-10 DOI: 10.1016/j.tet.2024.134301
Swapnil V. Halnor, Chepuri V. Ramana
{"title":"Attempted synthesis of the central 2,2-disubstituted pseudoindoxyl core of Austamide via a [Au]-catalyzed nitroalkyne cycloisomerization and intramolecular [3 + 2]-cycloaddition","authors":"Swapnil V. Halnor,&nbsp;Chepuri V. Ramana","doi":"10.1016/j.tet.2024.134301","DOIUrl":"10.1016/j.tet.2024.134301","url":null,"abstract":"<div><div>Herein, we describe an Au-catalyzed cycloisomerization process of a nitroalkyne that was projected to construct the central 2,2-disubstituted pseudoindoxyl core of the natural product Austamide. Our intended strategy for forging the pseudoindoxyl core is based on the nitroalkyne cycloisomerization followed by a subsequent intramolecular [3 + 2] cycloaddition. However, the [3 + 2] cycloaddition occurred in an undesired manner, ultimately leading to a complex hexacyclic scaffold.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134301"},"PeriodicalIF":2.1,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425123","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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