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An unexpected Michael type addition-deacylpyrazole involving coumarin-3-formylpyrazoles under mild conditions 温和条件下涉及香豆素-3-甲酰基吡唑的意想不到的迈克尔式加成-去酰基吡唑
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-08 DOI: 10.1016/j.tet.2024.134360
Chuan-Wen Lei , Jiao-Jiao Lei , Xiao-Li Feng , Wen-Hui Zhang , Ze-Gang Ma , You-Ping Tian , Ying Zhou
{"title":"An unexpected Michael type addition-deacylpyrazole involving coumarin-3-formylpyrazoles under mild conditions","authors":"Chuan-Wen Lei ,&nbsp;Jiao-Jiao Lei ,&nbsp;Xiao-Li Feng ,&nbsp;Wen-Hui Zhang ,&nbsp;Ze-Gang Ma ,&nbsp;You-Ping Tian ,&nbsp;Ying Zhou","doi":"10.1016/j.tet.2024.134360","DOIUrl":"10.1016/j.tet.2024.134360","url":null,"abstract":"<div><div>The first Michael type addition-deacylpyrazole involving α,β-unsaturated pyrazolamides was accomplished by utilizing DMAP as catalyst in mild condition. The protocol enables the access to various oxindole-substituted dihydrocoumarins from coumarin-3-formylpyrazoles and 3-acetoxy oxindoles in excellent yields (up to 99 % yield) with acceptable diastereoselectivities (up to &gt;95:5 dr). In this work, the acylpyrazole group of coumarin-3-formylpyrazoles acted as a temporary activating group for the first time. Detailed mechanistic studies were performed with high resolution mass spectrometry (HRMS) analysis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134360"},"PeriodicalIF":2.1,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657306","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 recent update on pallavicinia diterpenoids: Isolation, biogenetic pathway and total synthesis 关于 pallavicinia 二萜类化合物的最新进展：分离、生物遗传途径和全合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-07 DOI: 10.1016/j.tet.2024.134364
Xiwu Zhang, Ru Sun
{"title":"A recent update on pallavicinia diterpenoids: Isolation, biogenetic pathway and total synthesis","authors":"Xiwu Zhang,&nbsp;Ru Sun","doi":"10.1016/j.tet.2024.134364","DOIUrl":"10.1016/j.tet.2024.134364","url":null,"abstract":"<div><div><em>Pallavicinia</em> diterpenoids are isolated from the genus <em>Pallavicinia</em> of liverworts. Herein, the isolation, biogenetic pathway and total synthesis of <em>pallavicinia</em> diterpenoids with four distinct and complex skeletons were discribed. In this review, all successful total syntheses of 16 <em>pallavicinia</em> diterpenoids were introduced respectively in detail. These outstanding synthetic work will provide more inspiration and pave the stage for ingenious and efficient synthesis of newly discovered <em>pallavicinia</em> diterpenoids as well as other complex natural products, further promoting comprehensive biological evaluation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134364"},"PeriodicalIF":2.1,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657407","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 NAD+ with dually modified adenine for labeling ADP-ribosylation-specific proteins 用于标记 ADP-核糖基化特异性蛋白质的具有双重修饰腺嘌呤的 NAD+。
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-06 DOI: 10.1016/j.tet.2024.134361
Lei Zhang , Xiao-Nan Zhang , Arshad J. Ansari , Yong Zhang
{"title":"An NAD+ with dually modified adenine for labeling ADP-ribosylation-specific proteins","authors":"Lei Zhang ,&nbsp;Xiao-Nan Zhang ,&nbsp;Arshad J. Ansari ,&nbsp;Yong Zhang","doi":"10.1016/j.tet.2024.134361","DOIUrl":"10.1016/j.tet.2024.134361","url":null,"abstract":"<div><div>Protein adenosine diphosphate (ADP)-ribosylation participates in various pivotal cellular events. Its readers and erasers play key roles in modulating ADP-ribosylation-based signaling pathways. Unambiguous assignments of readers and erasers to individual ADP-ribosylated proteins provide insightful knowledge on ADP-ribosylation biology and require the development of tools and technologies for this goal. Herein, we report the design and the synthesis of a nicotinamide adenine dinucleotide (NAD<sup>+</sup>) carrying a photoactive and a clickable group. Functioning as a substrate for poly-ADP-ribosylation (PARylation), this NAD<sup>+</sup> mimic with dually modified adenine enables covalent crosslinking and labeling of proteins bound to PARylation, representing a new photoaffinity probe for studying this critical post-translational modification.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134361"},"PeriodicalIF":2.1,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646723","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
Chemical synthesis of 13C-labeled isopentenyl pyrophosphate 13C 标记的焦磷酸异戊烯酯的化学合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-04 DOI: 10.1016/j.tet.2024.134356
Ruoyao Liu , Zhiyuan Ren , Zixin Deng , Min Xu , Anwei Hou
{"title":"Chemical synthesis of 13C-labeled isopentenyl pyrophosphate","authors":"Ruoyao Liu ,&nbsp;Zhiyuan Ren ,&nbsp;Zixin Deng ,&nbsp;Min Xu ,&nbsp;Anwei Hou","doi":"10.1016/j.tet.2024.134356","DOIUrl":"10.1016/j.tet.2024.134356","url":null,"abstract":"<div><div>Isopentenyl pyrophosphate (IPP) is a key precursor in the biosynthesis of terpenoids, the largest class of natural products. <sup>13</sup>C isotope incorporation into the terpenoid scaffolds has been proved to be a powerful chemical probe to track the elusive cyclization mechanism of distinct terpene synthases which are the driving force for the tremendous chemical diversities seen in terpenoid natural products. Here, we present synthetic routes for the preparation of C1 to C5 individually <sup>13</sup>C labeled IPP starting from <sup>13</sup>C-labeled acetic acid and iodomethane, resulting in five distinct labeled substrates. The <sup>13</sup>C labeled IPP will be served as useful chemical probes to elucidate the new cyclization mechanisms catalyzed by those cryptic terpene synthases.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134356"},"PeriodicalIF":2.1,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654177","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
Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles enabled by a gold-catalyzed three-component reaction 通过金催化的三组分反应合成 1,3,5-三取代的 1,2,4-三唑
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-03 DOI: 10.1016/j.tet.2024.134358
Howard Díaz-Salazar, Carlos M. Ramírez-González, Miguel A. Rosas-Ortega, Susana Porcel
{"title":"Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles enabled by a gold-catalyzed three-component reaction","authors":"Howard Díaz-Salazar,&nbsp;Carlos M. Ramírez-González,&nbsp;Miguel A. Rosas-Ortega,&nbsp;Susana Porcel","doi":"10.1016/j.tet.2024.134358","DOIUrl":"10.1016/j.tet.2024.134358","url":null,"abstract":"<div><div>Valuable fully substituted 1,2,4-triazoles are obtained via a gold-catalyzed three-component reaction involving ethyl diazoacetate, aryldiazonium salts, and nitriles. The reaction proceeds under mild conditions, is regioselective, and allows the introduction of mono- and di-substituted aryl rings at the <em>ortho</em>, <em>meta,</em> and <em>para</em> positions. Mechanistic evidence suggests the participation of Au(III) species as the active catalysts.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134358"},"PeriodicalIF":2.1,"publicationDate":"2024-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592708","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
Transition-metal-free nucleophilic substitution of alkenyl boronic acids with propargylic mesylates sp3-carbon electrophiles 烯基硼酸与丙炔基甲磺酸酯 sp3 碳亲电体的无过渡金属亲核取代反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134353
Wenna Xie , Shiwen Liu , Bo Xu
{"title":"Transition-metal-free nucleophilic substitution of alkenyl boronic acids with propargylic mesylates sp3-carbon electrophiles","authors":"Wenna Xie ,&nbsp;Shiwen Liu ,&nbsp;Bo Xu","doi":"10.1016/j.tet.2024.134353","DOIUrl":"10.1016/j.tet.2024.134353","url":null,"abstract":"<div><div>We developed a highly versatile transition metal-free Suzuki type cross-coupling protocol. Alkenyl/aryl boronic acids could couple smoothly with propargylic mesylates Csp3 electrophiles in the presence of mild bases. The counterion in the base plays a crucial role for the reactivity. Our metal-free condition is orthogonal towards the classic transition metal catalysed Suzuki reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134353"},"PeriodicalIF":2.1,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142587327","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
Enhancing stability of cationic palladium complexes with hemilabile 2-benzyl oxazoline ligands: Structural insights and catalytic implications 增强具有半亲和 2-苄基噁唑啉配体的阳离子钯配合物的稳定性：结构见解和催化影响
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134348
Guldana Issabayeva , On-Yu Kang , Hyojung Ahn , Seong Jun Park , Hwan Jung Lim
{"title":"Enhancing stability of cationic palladium complexes with hemilabile 2-benzyl oxazoline ligands: Structural insights and catalytic implications","authors":"Guldana Issabayeva ,&nbsp;On-Yu Kang ,&nbsp;Hyojung Ahn ,&nbsp;Seong Jun Park ,&nbsp;Hwan Jung Lim","doi":"10.1016/j.tet.2024.134348","DOIUrl":"10.1016/j.tet.2024.134348","url":null,"abstract":"<div><div>This article describes the synthesis and characterization of Pd cationic complexes incorporating mono(2-benzyl oxazoline) ligands. Our study focuses on exploring the impact of electrostatic interactions of aromatic π-electrons of the benzyl group, aimed at enhancing the structural rigidity of cationic Pd complexes. Introduction of an aromatic moiety, which weakly coordinates with the Pd cation, led to a two-fold increase in the stability of the Pd cationic complex compared to complexes lacking any coordinating substituents. This research represents the initial instance of a cationic Pd complex with 2-benzyl oxazolines, highlighting the importance of weak electrostatic interactions in elucidating the three-dimensional structure of a metal complex.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134348"},"PeriodicalIF":2.1,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654178","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
Gold(III)-catalyzed regioselective synthesis of vinyl-substituted pyrazolo[1,4]-oxazepines via 7-exo-trig cyclization 金(III)催化的乙烯基取代的吡唑并[1,4]氮杂卓通过 7-exo-trig 环化的区域选择性合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-02 DOI: 10.1016/j.tet.2024.134340
Ravinder Guduru , Mathangi Sandeep , Komalla Sunil , N.S.V.M. Rao Mangina , Perla Bharath Kumar , Balasubramanian Sridhar , Galla V. Karunakar
{"title":"Gold(III)-catalyzed regioselective synthesis of vinyl-substituted pyrazolo[1,4]-oxazepines via 7-exo-trig cyclization","authors":"Ravinder Guduru ,&nbsp;Mathangi Sandeep ,&nbsp;Komalla Sunil ,&nbsp;N.S.V.M. Rao Mangina ,&nbsp;Perla Bharath Kumar ,&nbsp;Balasubramanian Sridhar ,&nbsp;Galla V. Karunakar","doi":"10.1016/j.tet.2024.134340","DOIUrl":"10.1016/j.tet.2024.134340","url":null,"abstract":"<div><div>Vinyl-substituted pyrazo[1,4]-oxazepines were prepared through an intramolecular regioselective cyclization method under gold catalysis. This organic transformation achieved selective C–N bond formation <em>via 7-exo-trig</em> cyclization, resulting in vinyl-containg pyrazolo[1,4]-benzooxazepines and pyrazolo[1,4]-naphthoxazepines in one-pot with moderate to very good yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134340"},"PeriodicalIF":2.1,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592623","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 quinolinium-based fluorescent probe for ultrafast detection of bisulfite and its applications in food detection, SO2 gas detection, and cell imaging 用于超快检测亚硫酸氢盐的喹啉基荧光探针及其在食品检测、二氧化硫气体检测和细胞成像中的应用
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-01 DOI: 10.1016/j.tet.2024.134355
Nan Liu , Zefei Lin , Ying Li, Chengyan Wu, Mingyu Tian, Lijun Tang
{"title":"A quinolinium-based fluorescent probe for ultrafast detection of bisulfite and its applications in food detection, SO2 gas detection, and cell imaging","authors":"Nan Liu ,&nbsp;Zefei Lin ,&nbsp;Ying Li,&nbsp;Chengyan Wu,&nbsp;Mingyu Tian,&nbsp;Lijun Tang","doi":"10.1016/j.tet.2024.134355","DOIUrl":"10.1016/j.tet.2024.134355","url":null,"abstract":"<div><div>Sulfur dioxide and its derivatives (HSO<sub>3</sub><sup>−</sup>/SO<sub>3</sub><sup>2-</sup>) play a crucial role in maintaining the redox balance of biological systems. Therefore, the development of effective detection methods for sulfur dioxide and its derivatives is of paramount importance. Herein, a novel fluorescent probe, <strong>QLN</strong>, was designed and synthesized using small molecule quinoline, demonstrating the capacity to recognize HSO<sub>3</sub><sup>−</sup> through Michael addition reaction. The probe <strong>QLN</strong> displayed good selectivity and anti-interference capabilities for HSO<sub>3</sub><sup>−</sup> recognition, effectively operating within a wide pH range (5–9) and exhibiting a rapid response time (&lt;5 s). Practical applications revealed the potential of probe <strong>QLN</strong> for detecting HSO<sub>3</sub><sup>−</sup> in living cells and food samples.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134355"},"PeriodicalIF":2.1,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142654176","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 progress in metal-catalyzed C(sp³)-P bond formation 金属催化 C(sp³)-P 键形成的最新进展
IF 2.1 3区 化学
Tetrahedron Pub Date : 2024-11-01 DOI: 10.1016/j.tet.2024.134352
Jia-Lin Tu , Zhengjia Shen , Binbin Huang
{"title":"Recent progress in metal-catalyzed C(sp³)-P bond formation","authors":"Jia-Lin Tu ,&nbsp;Zhengjia Shen ,&nbsp;Binbin Huang","doi":"10.1016/j.tet.2024.134352","DOIUrl":"10.1016/j.tet.2024.134352","url":null,"abstract":"<div><div>The construction of C(sp³)-P bonds is of paramount importance in organic synthesis, catalysis, and materials science. Organophosphorus compounds containing C(sp³)-P bonds serve as pivotal structural motifs in ligands, pharmaceuticals, agrochemicals, and functional materials. While traditional methods for C(sp³)-P bond formation largely rely on nucleophilic substitution or coupling of reactive organometallic reagents, recent years have witnessed significant advancements in metal-catalyzed approaches. This review highlights the recent developments in C(sp³)-P bond formation enabled by metals including Cu, Fe, Bi, Pd, Ni, Ru, Rh, and Co, with particular emphasis on methodologies that activate simple C(sp³)-H bonds or utilize readily available chemical feedstocks. Key mechanistic paradigms, including photoredox/transition metal dual catalysis, metal-catalyzed radical processes, and photo-induced ligand-to-metal charge transfer (LMCT), are critically discussed. This review evaluates the mechanistic insights, applications, and limitations of these methodologies in the synthesis of organophosphorus compounds, and provides perspectives on future directions to promote further advancements in C(sp³)-P bond formation strategies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134352"},"PeriodicalIF":2.1,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592592","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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