Tetrahedron最新文献_第9页

Investigation of the N2-Selective functionalization reaction of 2H-1,2,3-triazole catalyzed by a synergistic combination of copper and diamine ligands 铜与二胺配体协同组合催化2h -1,2,3-三唑n2选择性功能化反应的研究

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-03-01 Epub Date: 2025-12-13 DOI: 10.1016/j.tet.2025.135099

Aigui Zhang, Wenjing Luo, Zhonghua Qu, Weiqing Yang, Min Luo, Xin Li, Menglin Ma

{"title":"Investigation of the N2-Selective functionalization reaction of 2H-1,2,3-triazole catalyzed by a synergistic combination of copper and diamine ligands","authors":"Aigui Zhang, Wenjing Luo, Zhonghua Qu, Weiqing Yang, Min Luo, Xin Li, Menglin Ma","doi":"10.1016/j.tet.2025.135099","DOIUrl":"10.1016/j.tet.2025.135099","url":null,"abstract":"<div><div><em>N</em>-Aryl-1,2,3-triazole compounds are important pharmaceutical motifs synthesized via nucleophile reactions with triazoles. Typically, both <em>N</em><sup><em>2</em></sup> and <em>N</em><sup><em>1</em></sup> regioisomers are produced simultaneously. In this article, a synergistic catalytic system comprising CuI and 1,2-diphenylethylenediamine (DPEN) was employed for the selective <em>N</em><sup><em>2</em></sup>-coupling of 2-bromobenzoic acid with triazole. This reaction yielded 2-(2<em>H</em>-1,2,3-triazol-2-yl)benzoic acid (<strong>4a</strong>) with an impressive yield of 86 % and a regioselectivity of 91 % for the <em>N</em><sup><em>2</em></sup> isomer. Additionally, 2-bromobenzoic acid served as a cost-effective alternative to the traditionally used 2-iodobenzoic acid; notably, the reaction time was reduced from 4 h to 1.5 h. Mechanistic studies indicated that the DPEN ligand promotes carbon-copper bond formation, enhancing reaction activity and accelerating the overall rate; However, while there has been some improvement in <em>N</em><sup><em>2</em></sup> selectivity, it remains less than ideal.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135099"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786966","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

Phosphine-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes and conjugated dienes: Synthesis of 1,2,3,4-tetrahydrobenzofuro[3,2-b]pyridines 膦催化苯并呋喃衍生的氮杂烯和共轭二烯的[4 + 2]环加成：1,2,3,4-四氢苯并呋喃[3,2-b]吡啶的合成

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-03-01 Epub Date: 2025-12-14 DOI: 10.1016/j.tet.2025.135100

Shenao Qu , Yue Wang , Er-Qing Li

引用次数: 0

Photocatalytic deborative sulfonylation of alkenyl boronic acids with sulfonyl hydrazides under green environmental conditions 绿色环境条件下烯基硼酸与磺酰肼的光催化拆分磺化反应

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-03-01 Epub Date: 2025-12-11 DOI: 10.1016/j.tet.2025.135090

Divyani P. Patel, Vishwa K. Patel, Satish Kumar Singh

{"title":"Photocatalytic deborative sulfonylation of alkenyl boronic acids with sulfonyl hydrazides under green environmental conditions","authors":"Divyani P. Patel, Vishwa K. Patel, Satish Kumar Singh","doi":"10.1016/j.tet.2025.135090","DOIUrl":"10.1016/j.tet.2025.135090","url":null,"abstract":"<div><div>Vinyl sulfones are valued for their unique chemical properties and bioactivity, but creating a wide range of different analogs remains a challenge. To address this limitation, we have developed a novel and eco-friendly method for the synthesis of (<em>E</em>)-vinyl sulfones <em>via</em> visible light-mediated deborative sulfonylation of alkenyl boronic acids with sulfonyl hydrazides. Our straightforward and metal-free sulfonylation utilises eco-friendly visible light irradiation, and rose bengal organic dye, while a water-ethanol mixture serves as a green solvent, removing the necessity for external oxidants. The reaction delivers (<em>E</em>)-vinyl sulfones in good to excellent yields within a short reaction time and exhibits broad substrate scope with excellent functional group tolerance, including electron-rich, electron-poor, as well as aliphatic, heteroaryl, and sterically hindered substituent derivatives. Mechanistic investigations support a photoredox single-electron transfer (SET) pathway involving sulfonyl radicals. This mild and environmentally friendly protocol provides a valuable approach for the synthesis of bioactive (<em>E</em>)-vinyl sulfones, which are key structural motifs in pharmaceuticals, agrochemicals, and material science.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"191 ","pages":"Article 135090"},"PeriodicalIF":2.2,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145786973","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 the β-d-mannose containing tetrasaccharide repeating unit corresponding to the O-specific polysaccharide of Salmonella cerro O:18 含四糖重复单元的β-d-甘露糖的合成与沙门氏菌O特异性多糖对应

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-11-15 DOI: 10.1016/j.tet.2025.135065

Aniket Majhi, Samim Sahaji, Anup Kumar Misra

引用次数: 0

Recent advances in total syntheses of cage-like sesquiterpenoids 笼状倍半萜类化合物的全合成研究进展

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-27 DOI: 10.1016/j.tet.2025.135025

YunXia Yang, Xingang Xie, Xuegong She

引用次数: 0

Visible-light catalytic aerobic oxidation of aldehydes 可见光催化醛的好氧氧化

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-30 DOI: 10.1016/j.tet.2025.135039

Jia-Le Fu , Jia-Lun Luo , Xue-Feng Zhao , Dan Zhang , Tao Wu , Hongwei Si , Peng-Fei Dai

引用次数: 0

Mechanical force-induced luminescence enhancement and chromism of organic luminogens: synthesis, recent advances and perspectives 有机发光源的机械力致发光增强与致变色：合成、最新进展与展望

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-26 DOI: 10.1016/j.tet.2025.135023

Hanrong Liu, Junhui Jia

{"title":"Mechanical force-induced luminescence enhancement and chromism of organic luminogens: synthesis, recent advances and perspectives","authors":"Hanrong Liu, Junhui Jia","doi":"10.1016/j.tet.2025.135023","DOIUrl":"10.1016/j.tet.2025.135023","url":null,"abstract":"<div><div>Mechanochromic luminescent (MCL) materials are a class of novel intelligent materials that exhibit reversible change in luminescence color and/or intensity upon external mechanical force stimulation, demonstrating significant application potential in fields of force sensors, anti-counterfeiting materials, optical storage, bioimaging, and inkless printing, <em>etc</em>. Over the past few decades, in sharp contrast to the traditional fluorescence quenching phenomenon, MCL materials with enhanced luminescence effects have attracted considerable attention due to their unique “off-on” or “turn-on” behavior, where the luminescence intensity or efficiency significantly increased under mechanical force. Focusing on this intriguing property, this review summarizes the latest advances in “turn-on” MCL organic luminophores, categorizing them based on structural features and associated luminescence mechanisms. It emphasizes the critical roles of intermolecular interactions and packing modes in regulating mechanochromic behavior and mechanical force-induced luminescence enhancement performance. Furthermore, this review prospects future development directions and challenges for mechanical force-induced chromic materials with luminescence enhancement, including the development of novel high-efficiency materials, exploration of practical application potential, and in-depth investigation of underlying luminescence mechanisms.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135023"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145384502","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 practical and scalable synthetic protocol for α-trifluoromethylated indole-3-carbinols 一种实用且可扩展的α-三氟甲基化吲哚-3-甲醇合成方案

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-11-07 DOI: 10.1016/j.tet.2025.135044

Shikai Yang , Ziyan Wu , Xindi Li , Jinshan Li , Hongtao Liu , Juanzu Liu , Chunman Jia

引用次数: 0

Exploring the antibacterial potential of spirocyclic oxindole derivatives: Synthesis and biological evaluation 探索螺环氧吲哚衍生物的抗菌潜力：合成和生物学评价

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-30 DOI: 10.1016/j.tet.2025.135029

Olajide B. Omoyeni , Temitope O. Olomola , Nusrat O. Omisore , Taiwo F. Ojo , Craig A. Obafemi

{"title":"Exploring the antibacterial potential of spirocyclic oxindole derivatives: Synthesis and biological evaluation","authors":"Olajide B. Omoyeni , Temitope O. Olomola , Nusrat O. Omisore , Taiwo F. Ojo , Craig A. Obafemi","doi":"10.1016/j.tet.2025.135029","DOIUrl":"10.1016/j.tet.2025.135029","url":null,"abstract":"<div><div>A series of eight spirocyclic oxindole derivatives <strong>1a–1d</strong>, <strong>2a–2d</strong> was synthesized according to established methods; this included the previously unreported compound, <strong>2c</strong>. The structures of all compounds were unequivocally characterised by spectroscopic analysis (IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR) and high-resolution mass spectrometry (HRMS). The in vitro antibacterial activity was assessed against representative Gram-positive (<em>Bacillus subtilis</em>, <em>Bacillus anthracis</em>) and Gram-negative (<em>Escherichia coli</em>, <em>Pseudomonas aeruginosa</em>) bacterial strains by determining the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The compounds exhibited a range of bactericidal effects. Notably, derivative <strong>2c</strong> demonstrated potent, broad-spectrum activity against <em>B. subtilis</em>, <em>B. anthracis</em>, and <em>E. coli</em>. Furthermore, both <strong>2b</strong> and <strong>2c</strong> exhibited significant efficacy against a clinically resistant strain of <em>P. aeruginosa</em>. In contrast, compounds <strong>1a</strong> and <strong>1d</strong> showed negligible antibacterial activity. These results underscore the potential of the spirocyclic oxindole scaffold in the development of novel antibacterial agents. This study provides a foundation for future work to optimize the structure-activity relationship and elucidate the precise mechanism of action of these compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135029"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475105","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

Enantiospecific syntheses of (R)- and (S)-3-methylheneicosane, male-specific cuticular hydrocarbon of the crane fly Tipula autumnalis (Diptera: Tipulidae) (R)-和(S)-3-甲基苯二甲酸甲醚雄性特异性角质层碳氢化合物的合成（双翅目：提蝇科）

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-11-13 DOI: 10.1016/j.tet.2025.135063

João Pedro de Albuquerque Souza , Giuliana Pavaneli , Sandra Radžiutė , Caroline Da Ros Montes D'Oca , Vincas Būda , Paulo Henrique Gorgatti Zarbin

{"title":"Enantiospecific syntheses of (R)- and (S)-3-methylheneicosane, male-specific cuticular hydrocarbon of the crane fly Tipula autumnalis (Diptera: Tipulidae)","authors":"João Pedro de Albuquerque Souza , Giuliana Pavaneli , Sandra Radžiutė , Caroline Da Ros Montes D'Oca , Vincas Būda , Paulo Henrique Gorgatti Zarbin","doi":"10.1016/j.tet.2025.135063","DOIUrl":"10.1016/j.tet.2025.135063","url":null,"abstract":"<div><div>The chemical ecology of crane flies (Diptera: Tipulidae) has only recently begun to be elucidated, creating a pressing need for enantiomerically pure standards to support structural identification and functional studies. In a previous investigation, the cuticular hydrocarbons (<em>R</em>)- and (<em>S</em>)-3-methylheneicosane were identified as male-specific components of <em>Tipula autumnalis</em>, with synthetic samples enabling both confirmation of their stereostructures and assessment of biological activity. Laboratory bioassays revealed that the (<em>R</em>)-enantiomer elicited an excitatory response in males, whereas the (<em>S</em>)-enantiomer acted as a repellent. In the present work, we detail the total enantiospecific synthesis of these compounds from methyl (<em>S</em>)-3-hydroxy-2-methylpropionate precursor. The route employs orthogonal protection, Wittig coupling with a C17 fragment, hydrogenation, and terminal one-carbon homologation, providing efficient access to long-chain methyl-branched hydrocarbons with full stereochemical control. This work establishes a robust and generalizable strategy for the synthesis of enantioenriched methyl-branched hydrocarbons and provides sufficient material to support all future chemical and behavioral studies in this species, paving the way for the development of targeted insect management strategies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135063"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145527168","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