Tetrahedron最新文献_第5页

Electronic metal−support interaction of Pt1/V2O5 enables efficient and selective hydrogenation of aromatic nitros

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134433

Ziqi Bian , Xiaojun Zheng , Guoyong Xiao , Wanguo Wei , Cuiping Wang , Yuhui Zhao , Zhiqiang Zhang

{"title":"Electronic metal−support interaction of Pt1/V2O5 enables efficient and selective hydrogenation of aromatic nitros","authors":"Ziqi Bian , Xiaojun Zheng , Guoyong Xiao , Wanguo Wei , Cuiping Wang , Yuhui Zhao , Zhiqiang Zhang","doi":"10.1016/j.tet.2024.134433","DOIUrl":"10.1016/j.tet.2024.134433","url":null,"abstract":"<div><div>Arylamines play a key role in the synthesis of agricultural chemicals, dyes, medicine, rubber and other fine chemicals. The hydrogenation of aromatic nitro is the most convenient protocol for the preparation of arylamines. Therefore, it is of great research significance to develop a stable, efficient and low-cost catalyst in the hydrogenation of nitro compounds. Therefore, the supported single-atom platinum Pt<sub>1</sub>/V<sub>2</sub>O<sub>5</sub> (0.1 wt% of Pt by ICP−OES) was prepared for the efficient hydrogenation of variety of aromatic nitros. The Pt<sub>1</sub>/V<sub>2</sub>O<sub>5</sub> was characterized by SEM, TEM, HAADF−STEM, XRD, XPS, Raman and CO−DRIFT analysis. Amount of aromatic nitros with functional groups (such as CN and carbonyl groups) were hydrogenated smoothly to deliver the amines in 50–95 % yields. The catalytic performances are attributed to the electronic metal−support interactions between Pt<sub>1</sub> atoms and V<sub>2</sub>O<sub>5</sub> with the abundant surface oxygen vacancy, resulting in the enhanced electronic density of Pt<sub>1</sub> atoms, which were confirmed by the results of XPS and Raman spectra. The high activity and reusability of Pt<sub>1</sub>/V<sub>2</sub>O<sub>5</sub> catalyst imply its potential application in fine chemical synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134433"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143181108","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

Oxytrifluoromethylselenylation of olefins with N–SeCF3 saccharin as trifluoromethylselenylated reagent

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134419

Ke-Yi Xie , Yi-Nuo Zhu , Ming-Hui Shi, Ze-Dong Wang, Cong-Cong Zhang, Zhen-Tao Wang

引用次数: 0

Stereoselective synthesis of dihydrohydroxystreptose, virenose and l-evalose from a common precursor derived from l-arabinose

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134400

Sreevidya Pondla, Praveen Ambati, Kushaal Reddy Aramati, Ramu Sridhar Perali

引用次数: 0

Efficient synthesis of imidazo[1,5-a]pyridine sulfonamido derivative as a PARG inhibitor

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-31 DOI: 10.1016/j.tet.2025.134519

Chao Kan , Chongxun Ge , Song Liu , Song Shi , Hu He , Weike Su

引用次数: 0

Convenient synthesis and antiproliferative activity of 2-(Indol-2-yl)-2-arylacetamides

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-30 DOI: 10.1016/j.tet.2025.134515

Dmitrii A. Aksenov , Gilberto E. Fernandez , Iliya K. Kuzminov , Nikolai A. Arutiunov , Elena V. Aleksandrova , Alexander V. Aksenov , Alexandra Vernaza , Jeadyn Ramirez , Kieran Ross , Jadyn L. Smith , Liqin Du , Puppala Sathish , Dean J. Tantillo , Alexander Kornienko

{"title":"Convenient synthesis and antiproliferative activity of 2-(Indol-2-yl)-2-arylacetamides","authors":"Dmitrii A. Aksenov , Gilberto E. Fernandez , Iliya K. Kuzminov , Nikolai A. Arutiunov , Elena V. Aleksandrova , Alexander V. Aksenov , Alexandra Vernaza , Jeadyn Ramirez , Kieran Ross , Jadyn L. Smith , Liqin Du , Puppala Sathish , Dean J. Tantillo , Alexander Kornienko","doi":"10.1016/j.tet.2025.134515","DOIUrl":"10.1016/j.tet.2025.134515","url":null,"abstract":"<div><div>There have been a limited number of reports describing the preparation of 2-(indol-2-yl)-2-arylacetamides and those syntheses that have been published suffer from significant drawbacks. In addition, this class of compounds has not been evaluated biologically despite the occurrence of 2-(indol-2-yl)-acetamides in natural products and medicinally important compounds. We developed a two-step synthesis of these compounds utilizing our previously developed preparation of 2-(3-oxoindolin-ylidene)-2-arylacetonitriles from <em>o</em>-nitroacetophenones and their transformation into the desired compounds utilizing a novel process involving treatment under mild conditions with NaBH<sub>4</sub> in EtOH. The synthesized compounds were evaluated for antiproliferative effects against BE(2)-C neuroblastoma cells and two compounds were found to have micromolar IC<sub>50</sub> values.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134515"},"PeriodicalIF":2.1,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143346712","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

Controlled Electrochemical C4 Sulfonylation of 1(2H)-isoquinolone derivatives: Through the isomerization of N-radical to C-radical

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-28 DOI: 10.1016/j.tet.2025.134506

Weiwei Yao , Zixi Xie , Xinyu Liu , Zhenpu Wang , Fei Xue , Mengtao Ma

引用次数: 0

New gentisyl alcohol derivatives from Aspergillus japonicas collected from the Arctic 6700-4 sea area

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-27 DOI: 10.1016/j.tet.2025.134507

Man Zhang , Jia Rui , Chong Yu , Mengyang Sun , Dan Gou , Haifeng Wang , Guangyue Su

{"title":"New gentisyl alcohol derivatives from Aspergillus japonicas collected from the Arctic 6700-4 sea area","authors":"Man Zhang , Jia Rui , Chong Yu , Mengyang Sun , Dan Gou , Haifeng Wang , Guangyue Su","doi":"10.1016/j.tet.2025.134507","DOIUrl":"10.1016/j.tet.2025.134507","url":null,"abstract":"<div><div>Six compounds were isolated from the ethyl acetate extract of the marine fungus <em>Aspergillus japonicas</em>, which was collected from surface seawater in the Arctic 6700-4 sea area, including two new gentisyl alcohol derivatives named dimeric terrestrol I (<strong>1</strong>) and dimeric terrestrol J (<strong>2</strong>), along with four known compounds, dimeric terrestrol E (<strong>3</strong>), 2-(hydroxymethyl) benzene-1,4-diol (<strong>4</strong>), methyl (2′,5′-dihydroxyphenyl) acetate (<strong>5</strong>), and toluhydroquinone (<strong>6</strong>). All compounds were characterized and established by spectral analysis of 1D NMR and reported data, confirmed using 2D NMR and HR-MS for new compounds. All the compounds were tested for <em>in vitro</em> activity. The results show that dimeric terrestrol J (<strong>2</strong>), alleviated lipopolysaccharide (LPS)-induced BV2 microglial cell death by reducing the generation of nitric oxide (NO), has strong anti-inflammatory activity and is even stronger than Dexamethasone (DEX). Furthermore, molecular docking was conducted to verify the affinity between the protein and ligand.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134507"},"PeriodicalIF":2.1,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343116","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

An improved synthesis of 2-acetyl-1-pyrroline via the Grignard reaction in the presence of Et3N/TMSCl

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-27 DOI: 10.1016/j.tet.2025.134508

Shuting Yin , Fangyao Su , Jinlong Yu , Xixuan Zhao , Yongguo Liu , Sen Liang , Baoguo Sun , Hongyu Tian , Shuang Bai

{"title":"An improved synthesis of 2-acetyl-1-pyrroline via the Grignard reaction in the presence of Et3N/TMSCl","authors":"Shuting Yin , Fangyao Su , Jinlong Yu , Xixuan Zhao , Yongguo Liu , Sen Liang , Baoguo Sun , Hongyu Tian , Shuang Bai","doi":"10.1016/j.tet.2025.134508","DOIUrl":"10.1016/j.tet.2025.134508","url":null,"abstract":"<div><div>2-Acetyl-1-pyrroline is the most important flavor compound of rice. However, despite its high practical value as a flavoring compound, its synthesis remains a considerable challenge. This study developed a simplified and practical approach for synthesizing 2-acetyl-1-pyrroline, using methyl prolinate as the starting material through a Grignard reaction of 2-(methoxycarbonyl)-1-pyrroline with MeMgBr in the presence of Et<sub>3</sub>N/TMSCl or TMSOTf. It was found that adding Et<sub>3</sub>N/TMSCl or TMSOTf during the Grignard reaction effectively suppresses the formation of the byproduct, the tertiary alcohol 2-(1-hydroxy-1-methylethyl)-1-pyrroline, which results from the excessive addition of the Grignard reagent. This optimized method consistently achieves stable yields of around 50 %. Furthermore, the study analyzes and discusses the formation of an isomer of 2-acetyl-1-pyrroline, specifically 6-methyl-5-oxo-2,3,4,5-tetrahydropyridine, as well as the reactivity of the 2-(methoxycarbonyl)-1-pyrroline intermediate. These findings have important implications for understanding the stability and potential applications of 2-acetyl-1-pyrroline in flavoring.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134508"},"PeriodicalIF":2.1,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143360825","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

Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-26 DOI: 10.1016/j.tet.2025.134497

Yan-Ning Niu , Ke-Yu Wang , Feng-Yan Han , Xiao-Feng Xia

引用次数: 0

First stereoselective total synthesis and stereochemical revision of Vittarilide-B using a carbohydrate-based strategy

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-01-25 DOI: 10.1016/j.tet.2025.134499

Rajashekar Reddy Nimmareddy , Rajitha Nimmareddy , Himabindu Gandham , Raju Doddipalla , Madhu Sriramadasu , Krishnakanth Reddy Leleti

{"title":"First stereoselective total synthesis and stereochemical revision of Vittarilide-B using a carbohydrate-based strategy","authors":"Rajashekar Reddy Nimmareddy , Rajitha Nimmareddy , Himabindu Gandham , Raju Doddipalla , Madhu Sriramadasu , Krishnakanth Reddy Leleti","doi":"10.1016/j.tet.2025.134499","DOIUrl":"10.1016/j.tet.2025.134499","url":null,"abstract":"<div><div>The first stereoselective total synthesis of Vittarilide-B and its revised structure have been successfully accomplished. The synthesis began with D-glucal as the starting material, which was transformed into the reported structure of Vittarilide-B. Although the <sup>1</sup>H NMR, <sup>13</sup>C NMR, and NOE data for the synthesized compound corresponded to the naturally isolated structure, the optical rotation was inconsistent. This discrepancy necessitated the synthesis of the enantiomer using <span>l</span>-rhamnose as the starting material, which yielded an optical rotation consistent with that of the isolated compound. The synthesis involved the preparation of 5-deoxy-D-arabinono-1,4-lactone via RuO<sub>4</sub>-catalyzed oxidative cleavage of 6-deoxyglucal diacetate derived from D-glucal, followed by alkaline hydrolysis. The lactone was then protected with TBS, esterified with TBS-protected caffeic acid, and deprotected to afford Vittarilide-B. This synthesis not only confirmed the structure of Vittarilide-B but also resulted in the stereochemistry revision of the natural product. The revised structure was synthesized using a product whose spectral data precisely matched the reported data of Vittarilide-B, representing a noteworthy contribution to the Vittarilide family of compounds. This concise synthetic approach provides access to Vittarilide-B its stereoisomer, enabling further investigation of their biological activities.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134499"},"PeriodicalIF":2.1,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343121","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