Tetrahedron最新文献

Transition metal-catalyzed P(O)–H alkenylation, allenylation and alkynylation reactions: A recent trend

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-28 DOI: 10.1016/j.tet.2024.134388

Haoran Yang , Shaoqing Liu , Ruwei Shen , Li-Biao Han

引用次数: 0

Photoredox catalyzed multi component synthesis of indolyl-4H-chromenes via HAT

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-26 DOI: 10.1016/j.tet.2024.134386

Shraddha Tivari , Mohd Zaheeruddin Beg , Akanksha Kashyap , Pravin K. Singh , Praveen P. Singh , Sudhanshu Kanaujia , Vishal Srivastava

引用次数: 0

Metal catalyst-free β-amination of branched rac-C8N-type such as C7N carbasugars via intramolecular aza-michael addition: Biological evolution, DFT studies and ADME properties

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-25 DOI: 10.1016/j.tet.2024.134384

Arif Baran , Tahir Savran , Gökay Aydın , Mustafa Emirik

{"title":"Metal catalyst-free β-amination of branched rac-C8N-type such as C7N carbasugars via intramolecular aza-michael addition: Biological evolution, DFT studies and ADME properties","authors":"Arif Baran , Tahir Savran , Gökay Aydın , Mustafa Emirik","doi":"10.1016/j.tet.2024.134384","DOIUrl":"10.1016/j.tet.2024.134384","url":null,"abstract":"<div><div>In this study, a new stereospecific strategy for the preparation of C<sub>8</sub>N aminocyclohexenols such as C<sub>7</sub>N, validamine analogs were developed from starting compound <strong>4</strong> via intramolecular <em>aza</em>-michael <em>β</em>-amination reaction between <em>α</em>, <em>β</em>-unsaturated ketones and ammonia in methanol. The strategy was to produce C<sub>8</sub>N derivatives such as validamine C<sub>7</sub>N via Kornblum-DeLaMare rearrangement, which involves stereocontrolled amination of a double bond, esterification, carbonyl group reduction, benzofuran ring opening, ammonolysis of acetate groups. The mechanism of target molecules is discussed. Pseudosugars with different configurations containing an amino group at the anomeric position were tested against <em>α</em>-glucosidase, <em>β</em>-glucosidase, and <em>α</em>-amylase. Among these compounds, compound <strong>12</strong> against <em>α</em>-glucosidase, compound <strong>14</strong> against <em>β</em>-glucosidase, and compound <strong>21</strong> against <em>α</em>-amylase exhibited the best activity compared to acarbose. Moreover, enzyme kinetic studies to understand the enzyme inhibition mechanism and DFT studies to investigate binding interactions with enzyme active sites were performed on these compounds (<strong>12</strong>, <strong>14</strong>, and <strong>21</strong>). Additionally, the pharmacokinetic parameters (ADME) were examined using the QikProp module to determine their potential as drug candidates.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"170 ","pages":"Article 134384"},"PeriodicalIF":2.1,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142743628","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

Cyclodextrins functionalized polyvinylidene fluoride membranes: Strategies and diverse applications 环糊精功能化聚偏氟乙烯膜：策略和多样化应用

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-21 DOI: 10.1016/j.tet.2024.134385

Mohamed Magdi Ahmed , Dominika Nowacka , Anna Maria Skwierawska , Michal Řezanka

{"title":"Cyclodextrins functionalized polyvinylidene fluoride membranes: Strategies and diverse applications","authors":"Mohamed Magdi Ahmed , Dominika Nowacka , Anna Maria Skwierawska , Michal Řezanka","doi":"10.1016/j.tet.2024.134385","DOIUrl":"10.1016/j.tet.2024.134385","url":null,"abstract":"<div><div>Cyclodextrin (CD)-functionalized membranes represent a promising advancement in the domain of organic chemistry, particularly in the development of functional materials. The unique toroidal structure of CDs facilitates their well-known host-guest interactions, enabling the encapsulation of various organic molecules and enhancing the adsorption capabilities of membranes. Functionalization of polyvinylidene fluoride (PVDF) membranes with CDs addresses the challenges posed by the hydrophobicity of PVDF, such as membrane fouling, permeability, and selectivity. This modification not only improves membrane performance but also expands its potential applications in areas such as water treatment, sensing, and biomaterials. This review provides a detailed examination of the synthetic strategies employed to achieve CD functionalization on PVDF, considering the chemical inertness of the polymer and the stability of the resulting materials. The performance of these CD-functionalized PVDF membranes is critically analyzed and the study highlights the intersection of organic synthesis, supramolecular chemistry, and material science, contributing to the development of advanced functional materials with broad applicability.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"170 ","pages":"Article 134385"},"PeriodicalIF":2.1,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142719771","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 advances in the synthesis of azetidines 氮杂环丁烷合成的最新进展

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-19 DOI: 10.1016/j.tet.2024.134383

Vahideh Zadsirjan, Fatemeh Soleimani

引用次数: 0

Structural optimization of pyridine quinoxaline cobalt (II) catalysts for MMA polymerization based on systematical SCSC transformation study 基于系统 SCSC 转化研究的用于 MMA 聚合的吡啶喹喔啉钴 (II) 催化剂的结构优化

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-19 DOI: 10.1016/j.tet.2024.134370

Biyun Su , Qi Zhang , Paison Faida , Dou Yang , Liqin Ding , Boli Hou

{"title":"Structural optimization of pyridine quinoxaline cobalt (II) catalysts for MMA polymerization based on systematical SCSC transformation study","authors":"Biyun Su , Qi Zhang , Paison Faida , Dou Yang , Liqin Ding , Boli Hou","doi":"10.1016/j.tet.2024.134370","DOIUrl":"10.1016/j.tet.2024.134370","url":null,"abstract":"<div><div>The Schiff base condensation reaction was adopted to synthesize a series of pyridine-based quinoxaline ligands (<strong>L1, L2, L3, L4</strong>) using 2-acetylpyridine and 1,2-phenylenediamine aromatic amines with different substituents of –OCH<sub>3</sub>, –F, -Cl, -Br. Then, four symmetrical dinuclear metal complexes (<strong>1–4</strong>) were obtained by coordination reaction of the synthesized ligands with CoCl<sub>2</sub>·6H<sub>2</sub>O, and six unexpectedly systematic and novel solvent-involved asymmetric mononuclear metal complexes (<strong>1A-4A, 3B, 4B</strong>) were obtained during single crystals cultivating by solvent diffusion method. The microscopic composition of the complexes were proved by a series of characterizations such as elemental analysis, IR and UV–vis. At the same time, by improving the single crystal culture technology, full crystal sample of compounds was obtained and X-ray single crystal diffraction showed a rare single crystal to single crystal structure transition (SCSC) phenomenon in this study. Furthermore, the catalytic properties of the complexes for MMA polymerization was explored, it was found that the catalytic activity of complexes <strong>1–4</strong> containing different types of substituents on pyridyl quinoxaline ligand was in the order of <strong>1 < 2</strong> < <strong>3 < 4</strong>, indicating that the complex with an electron-withdrawing substituent showed the higher activity than that of electron-donating substituent. Complexes <strong>1A-4A, 3B</strong> and <strong>4B</strong> showed higher catalytic activity in MMA polymerization than <strong>1–4</strong>, which confirmed that the catalytic activity of mononuclear complexes were generally higher than that of binuclear complexes.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"170 ","pages":"Article 134370"},"PeriodicalIF":2.1,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142719774","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

Thiophene-substituted quinoxaline donor-acceptor dyes: Synthesis, NMR spectroscopy, X-ray crystallography, and photophysical properties 噻吩取代喹喔啉供体-受体染料：合成、核磁共振光谱学、X 射线晶体学和光物理性质

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-18 DOI: 10.1016/j.tet.2024.134382

Brett M. Lucht , Richard J. Monsky , Michael C. Rosko , Joseph M. Tanski , Jocelyn M. Nadeau

{"title":"Thiophene-substituted quinoxaline donor-acceptor dyes: Synthesis, NMR spectroscopy, X-ray crystallography, and photophysical properties","authors":"Brett M. Lucht , Richard J. Monsky , Michael C. Rosko , Joseph M. Tanski , Jocelyn M. Nadeau","doi":"10.1016/j.tet.2024.134382","DOIUrl":"10.1016/j.tet.2024.134382","url":null,"abstract":"<div><div>Structure-property relationship studies of fluorescent molecules containing donor-acceptor units are important for informing the design of organic materials for custom applications. We report the synthesis and characterization of a series of novel thiophene-substituted quinoxaline donor-acceptor dyes with varied substituent positioning. The dyes were synthesized using microwave-assisted methods in one or two steps from commercially available precursors. In solution, proton NMR spectroscopy studies revealed significant upfield shifts for certain thiophene ring protons in the <em>o</em>-disubstituted quinoxaline derivatives compared to their monosubstituted analogs. The upfield shifts resulted from restricted rotation about the thiophene-quinoxaline C–C bonds due to steric congestion leading to some protons being shielded by neighboring aromatic rings. In the solid state, single-crystal X-ray diffraction studies of the <em>o</em>-disubstituted derivatives showed that they exhibit thiophene ring disorder. These dyes are weakly emissive in solution, and their photophysical characterization using UV–vis and fluorescence spectroscopy in solvents of varying polarity revealed slight to moderate emission solvatochromism, with Lippert-Mataga analysis estimated Δμ values between 3 and 6 D. The dyes with thiophene rings attached to the benzene side of the quinoxaline ring exhibited a higher degree of solvatochromism than those with thiophene rings attached to the pyrazine side, illustrating the impact that substituent positioning can have on a molecule's photophysical properties. DFT and TD-DFT computational results were consistent with the observed photophysical properties and electronic structures of the dyes and aided in rationalization of the trends.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"170 ","pages":"Article 134382"},"PeriodicalIF":2.1,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142720377","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

Ullmann coupling reaction of dihalobenzenes and malononitrile-heterocumulene adducts under ultrasound-irradiation 超声辐照下二卤苯和丙二腈-杂茂烯加合物的乌尔曼偶联反应

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-16 DOI: 10.1016/j.tet.2024.134381

Manijeh Nematpour

引用次数: 0

Synthesis of dendritic self-immolative molecules triggered by reactive electrophilic alkylating agents: Assessment for colorimetric disclosure of such agents 由活性亲电烷基化剂引发的树枝状自褪色分子的合成：评估此类制剂的比色法披露

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-14 DOI: 10.1016/j.tet.2024.134377

Alexander G. Gavriel , Flavien Leroux , Ann M. Chippindale , Mark R. Sambrook , Wayne Hayes , Andrew T. Russell

{"title":"Synthesis of dendritic self-immolative molecules triggered by reactive electrophilic alkylating agents: Assessment for colorimetric disclosure of such agents","authors":"Alexander G. Gavriel , Flavien Leroux , Ann M. Chippindale , Mark R. Sambrook , Wayne Hayes , Andrew T. Russell","doi":"10.1016/j.tet.2024.134377","DOIUrl":"10.1016/j.tet.2024.134377","url":null,"abstract":"<div><div>The development of efficient chemoselective self-immolative molecules for use as sensors necessitates optimization of the degradation characteristics of the self-immolative unit to permit effective signal generation (e.g. colour changes) in relation to the triggering event. One approach is to utilise degradable dendritic structures to allow multiple copies of signalling molecules to be released in return for a single triggering event. To this end, degradable isomeric dendrons featuring aniline-core units for the detection of reactive electrophilic species have been prepared and their reactions studied. A route employing protected phosphorous-borane adducts was key to their synthesis. Following deprotection of these adducts, to activate the self-immolative dendron, alkylation by an electrophilic species and subsequent elimination events, under basic conditions as employed for related molecules incapable of generating an amplified response, were investigated. These studies revealed, in contrast to the findings with other structurally-related self-immolative dendritic molecules, that the degradation profiles of these dendrons do not afford amplified responses in relation to the number of triggering events. In the light of the expenditure of resources required to generate well-defined dendritic materials, this study provides a cautionary perspective against the assumption that such branched molecules will always afford an amplified signal.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"169 ","pages":"Article 134377"},"PeriodicalIF":2.1,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142657308","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

Michael reaction of enyne derivatives of Meldrum's acid in water: Synthetic approach for creating a C–N/C–S bonds inwith low reactive nucleophiles Meldrum's 酸的炔衍生物在水中的迈克尔反应：在低活性亲核物中生成 C-N/C-S 键的合成方法

IF 2.1 3区化学

Tetrahedron Pub Date : 2024-11-14 DOI: 10.1016/j.tet.2024.134369

Sergey A. Sokov , Gulnara Z. Raskildina , Anna V. Vologzhanina , Simon S. Zlotskii , Alexander A. Golovanov

引用次数: 0