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Formation of triarylphosphines via PH/CF cross coupling reactions catalyzed by nickel
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155445
Meng-Ting Xiang , Lei Fan , Qian Xu , Li Zhang , Shuai Wang , Hong Zhong , Jia Yang
{"title":"Formation of triarylphosphines via PH/CF cross coupling reactions catalyzed by nickel","authors":"Meng-Ting Xiang ,&nbsp;Lei Fan ,&nbsp;Qian Xu ,&nbsp;Li Zhang ,&nbsp;Shuai Wang ,&nbsp;Hong Zhong ,&nbsp;Jia Yang","doi":"10.1016/j.tetlet.2024.155445","DOIUrl":"10.1016/j.tetlet.2024.155445","url":null,"abstract":"<div><div>Herein, a nickel-catalyzed coupling reaction of monofluoroarenes or polyfluoroarenes with diphenyl phosphine to construct C(sp<sup>2</sup>)<img>P bond through C<img>F bond functionalization is disclosed. The reaction can be carried out successfully to produce the corresponding triarylphosphine or fluorinated triarylphosphine compounds with good to high yields, providing a new method for the synthesis of fluorine-containing organophosphine compounds via the formation of C<img>P bond.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155445"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159668","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 development of bibenzo[c]thiophene derivatives for application in functional materials
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155393
Yousuke Ooyama, Keiichi Imato
{"title":"Recent advances in development of bibenzo[c]thiophene derivatives for application in functional materials","authors":"Yousuke Ooyama,&nbsp;Keiichi Imato","doi":"10.1016/j.tetlet.2024.155393","DOIUrl":"10.1016/j.tetlet.2024.155393","url":null,"abstract":"<div><div>1,1′- and 4,4′-bibenzo[<em>c</em>]thiophenes as the 1,1′-dimer and 4,4′-dimer of benzo[<em>c</em>]thiophene, respectively, have gained more and more attention in recent years because of pioneering challenge to the development of facile and efficient synthetic method and their attractive photophysical and electrochemical properties to be a promising fluorophore and photosensitizer for highly efficient bioimaging, phototheranostics, and optoelectronic devices. Thus, this review is focused on development of bibenzo[<em>c</em>]thiophene derivatives and their potential as a π-building block for creating new functional materials. First, synthetic methods for 1,1′- and 4,4′-bibenzo[<em>c</em>]thiophene derivatives, and their photophysical and electrochemical properties such as photoabsroption, fluorescence, and redox properties and HOMO and LUMO energy levels are discussed. Moreover, we present not only a practical application of bibenzo[<em>c</em>]thiophene unit to optoelectronic devices and fluorescence bioimaging and phototherapy bust also creation of a new-type functional dye material composed of bibenzo[<em>c</em>]thiophene skeleton.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155393"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159526","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Convenient synthesis of highly functionalized isoxazoles including an amidine skeleton based on trichloroacetamidine, alkynes, and hydroxyimidoyl chloride
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155443
Manijeh Nematpour
{"title":"Convenient synthesis of highly functionalized isoxazoles including an amidine skeleton based on trichloroacetamidine, alkynes, and hydroxyimidoyl chloride","authors":"Manijeh Nematpour","doi":"10.1016/j.tetlet.2024.155443","DOIUrl":"10.1016/j.tetlet.2024.155443","url":null,"abstract":"<div><div>The synthesis of functionalized isoxazole-4-carboximidamide with appropriate yields through a novel four-component reaction from alkynes, hydroxyimidoyl chloride, trichloroacetonitrile, and various amines is a remarkable achievement in heterocycle chemistry. This strategy offers a direct and efficient route to access different isoxazoles with amidine substitution from readily available starting materials. The use of copper (I) as a catalyst, without adding ligand, in THF solvent, and with the help of ultrasonic conditions for 45 min at room temperature highlights the importance of transition metal catalysis in this process.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155443"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Iron-catalyzed one-pot tandem oxidation/acylation/dearomatization of biaryl ynones with benzyl alcohols: access to diversified acylated spiro[5.5]trienones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2025.155469
Dong Xia , Yanfeng Miao , Hongjian Ji , Wenchao Yang , Yun Shi
{"title":"Iron-catalyzed one-pot tandem oxidation/acylation/dearomatization of biaryl ynones with benzyl alcohols: access to diversified acylated spiro[5.5]trienones","authors":"Dong Xia ,&nbsp;Yanfeng Miao ,&nbsp;Hongjian Ji ,&nbsp;Wenchao Yang ,&nbsp;Yun Shi","doi":"10.1016/j.tetlet.2025.155469","DOIUrl":"10.1016/j.tetlet.2025.155469","url":null,"abstract":"<div><div>A new iron-catalyzed tandem cyclization and 6-<em>exo</em>-trig dearomatization reaction of biaryl ynones with readily available benzyl alcohols was developed. In the presence of Fe(acac)<sub>3</sub> and <em>tert</em>-butyl hydroperoxide,a variety of acylated spiro[5.5]trienones were prepared through cascade oxidation/acylation/dearomatization process using benzyl alcohols as acylation reagent.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155469"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143324809","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Enzymatic synthesis and characterization of nicotinamide riboside pseudouridine diphosphate
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155432
Yinghan Hu , Xueying Wang , Yanzhe Huang , Xiaojia Guo , Haizhao Xue , Martin Pfeiffer , Bernd Nidetzky , Zongbao K. Zhao
{"title":"Enzymatic synthesis and characterization of nicotinamide riboside pseudouridine diphosphate","authors":"Yinghan Hu ,&nbsp;Xueying Wang ,&nbsp;Yanzhe Huang ,&nbsp;Xiaojia Guo ,&nbsp;Haizhao Xue ,&nbsp;Martin Pfeiffer ,&nbsp;Bernd Nidetzky ,&nbsp;Zongbao K. Zhao","doi":"10.1016/j.tetlet.2024.155432","DOIUrl":"10.1016/j.tetlet.2024.155432","url":null,"abstract":"<div><div>Nicotinamide adenine dinucleotide (NAD) analogs are of great interests for chemical and biological applications. In this work, a novel NAD analog, nicotinamide riboside pseudouridine diphosphate (NpUD) was synthesized via coupling of pseudouridine triphosphate and nicotinamide mononucleotide catalyzed by a mutant of nicotinic acid mononucleotide adenylyltransferase. It was found that NpUD is more stable than NAD against a common pyrophosphatase NudC found in <em>Escherichia coli</em>. Interestingly, NpUD could function as redox cofactor for several oxidoreductases, among them a mutant methanol dehydrogenase showed 1.9-fold higher activity with NpUD than that with NAD. Overall, the results offer opportunities to explore NpUD in other applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155432"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159577","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Regioselective synthesis of quaternized cellulose nanocrystals and its antibacterial properties in clinical isolates of methicillin-resistant Staphylococcus aureus
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155420
Nadarajah Vasanthan, Dong Kwon, Steven Furman
{"title":"Regioselective synthesis of quaternized cellulose nanocrystals and its antibacterial properties in clinical isolates of methicillin-resistant Staphylococcus aureus","authors":"Nadarajah Vasanthan,&nbsp;Dong Kwon,&nbsp;Steven Furman","doi":"10.1016/j.tetlet.2024.155420","DOIUrl":"10.1016/j.tetlet.2024.155420","url":null,"abstract":"<div><div>Quaternized cellulose nanocrystals (CNCs) were prepared by chloroacetylation and subsequent reaction with tertiary amines. The chloroacetylation of CNCs and quaternary ammonium-modified CNCs were characterized by the analysis of FTIR and solid-state NMR spectroscopies. Chloroacetylation of CNCs was found to be highly regioselective. CNCs can be chemically modified to tailor their properties to improve dispersion in the polymer matrix, which expands the application of CNCs as reinforcing materials. Biological evaluation of the ammonium-modified compounds was conducted using the disc diffusion test, minimum bactericidal concentration, and bacterial killing pattern for methicillin-associated multidrug-resistant clinical isolates of <em>Staphylococcus aureus</em>, one of the most problematic bacterial human pathogens. Results showed that the CNC with alkyl chains with 16 carbons had more antibacterial properties than that of 10 carbons against all tested clinical isolates of <em>Staphylococcus aureus</em> regardless of antibiotic resistance or sensitivity. This finding suggests that the ammonium-modified CNCs may be applicable to treat <em>Staphylococcus aureus</em> infections.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155420"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159579","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Facile and diverse synthesis of indolyl substituted 4,5,6,7-tetrahydro-4H-indol-4-ones and 1,6-dihydropyrrolo[2,3-c]pyrazol via multi-component reactions
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155444
Jing Wang , Lu Yu , Haoqiang Jiang , Songlei Zhu
{"title":"Facile and diverse synthesis of indolyl substituted 4,5,6,7-tetrahydro-4H-indol-4-ones and 1,6-dihydropyrrolo[2,3-c]pyrazol via multi-component reactions","authors":"Jing Wang ,&nbsp;Lu Yu ,&nbsp;Haoqiang Jiang ,&nbsp;Songlei Zhu","doi":"10.1016/j.tetlet.2024.155444","DOIUrl":"10.1016/j.tetlet.2024.155444","url":null,"abstract":"<div><div>An efficient and facile protocol for the synthesis of some novel 4,5,6,7-tetrahydro-4H-indol-4-ones, 1,6-dihydropyrrolo[2,3-<em>c</em>]pyrazol and 1,4-dihydrochromeno [4,3-<em>b</em>]pyrrol by one-pot three-component reaction of 3-cyanoacetyl indoles, arylglyoxal monohydrate and various enaminones, pyrazol-5-amines or 4-amino coumarin. The advantages of this method include the availability of starting materials, mild reaction conditions and good yields of products, operational simplicity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155444"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Asymmetric one-pot synthesis of trans-stilbene oxide via desymmetrizing monosulfonylation of meso-hydrobenzoin catalyzed by a chiral bisoxazoline–copper (II) complex
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155435
Kenji Yatsuzuka, Midori Kawasaki, Ryuichi Shirai
{"title":"Asymmetric one-pot synthesis of trans-stilbene oxide via desymmetrizing monosulfonylation of meso-hydrobenzoin catalyzed by a chiral bisoxazoline–copper (II) complex","authors":"Kenji Yatsuzuka,&nbsp;Midori Kawasaki,&nbsp;Ryuichi Shirai","doi":"10.1016/j.tetlet.2024.155435","DOIUrl":"10.1016/j.tetlet.2024.155435","url":null,"abstract":"<div><div>Chiral stilbene oxides are useful and versatile intermediates for the synthesis of chiral ligands for asymmetric catalysis, chiral auxiliaries for diastereoselective transformations, and precursors for chiral building blocks of many compounds. We achieved the enantioselective desymmetric tosylation of <em>meso</em>-hydrobenzoin catalyzed by a chiral ligand–CuCl<sub>2</sub> complex followed by base promoted intramolecular cyclization to furnish <em>trans</em>-stilbene oxide in high yield with excellent enantioselectivity up to 99 %ee in a one-pot operation. This simple transformation offers the most feasible and promising option for the asymmetric synthesis of stilbene oxides with high optical purity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155435"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159575","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Unified synthesis of DSPC and PSPC: Chemical entities of hydrogenated soy L-α-phosphatidylcholine (HSPC), a key component of liposomal drug formulations
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155424
Pallavi Rao, Madhavachary Rudrakshula, Rajendar Potham, Rahul Varma Katari, Vishnuvardhana Vema Reddy Eda, Saikat Sen, Srinivas Oruganti
{"title":"Unified synthesis of DSPC and PSPC: Chemical entities of hydrogenated soy L-α-phosphatidylcholine (HSPC), a key component of liposomal drug formulations","authors":"Pallavi Rao,&nbsp;Madhavachary Rudrakshula,&nbsp;Rajendar Potham,&nbsp;Rahul Varma Katari,&nbsp;Vishnuvardhana Vema Reddy Eda,&nbsp;Saikat Sen,&nbsp;Srinivas Oruganti","doi":"10.1016/j.tetlet.2024.155424","DOIUrl":"10.1016/j.tetlet.2024.155424","url":null,"abstract":"<div><div>A simple, unified and scalable strategy, emanating from the readily available chiral pool <span>d</span>-solketal, has been employed to obtain the enantiomerically pure components of hydrogenated soy L-α-phosphatidylcholine (HSPC), namely distearoyl phosphatidylcholine (DSPC) and 1-palmitoyl-2-stearoyl-phosphatidylcholine (PSPC). HSPC is obtained by hydrogenating naturally occurring soy L-α-lecithin; this affords a glycerophospholipid mixture containing C-16 (minor) or C-18 (major) fatty acid chain at <em>sn</em>-1, C-18 chain at <em>sn</em>-2 position and phosphatidylcholine at <em>sn</em>-3 position. HSPC already has numerous applications as an excipient and essential component in many FDA approved liposomal drug formulations such as Doxil® (doxorubicin HCl liposome injection) and AmBisome® (amphotericin B liposome injection). However, there is increasing interest in uncovering the potential individual applications of its components, DSPC and PSPC, too. In this context, the current synthesis offers a strategy to have a ready bespoke access to multi-gram quantities of DSPC and PSPC (in particular) that does not rely on tedious separation of the components of HSPC.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155424"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159666","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
O-Alkylation of hydroxypyridines and derivatives via transient alkyl diazonium species
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155396
Guillaume Reynard , Calvine Lai , Emna Azek , Hélène Lebel
{"title":"O-Alkylation of hydroxypyridines and derivatives via transient alkyl diazonium species","authors":"Guillaume Reynard ,&nbsp;Calvine Lai ,&nbsp;Emna Azek ,&nbsp;Hélène Lebel","doi":"10.1016/j.tetlet.2024.155396","DOIUrl":"10.1016/j.tetlet.2024.155396","url":null,"abstract":"<div><div>Diazotisation of amines with a nitrite reagent was performed in the presence of hydroxy-pyridines and derivatives to give the alkylation products. The <em>O</em>-alkylation product was isolated from 2-, 3-, 4-hydroxypyridines, 2-hydroxyquinoline and 2-hydroxypyrimidines. In the case of 2-hydropyridines, the <em>N</em>-alkylation product was also observed, with the <em>O</em>-alkylation product being favoured. The reaction conditions were compatible with a variety of functional groups, and namely amino alcohols were successfully reacted to afford hydroxy-substituted products. The distinctive reactivity of dinitrites in comparison to mononitrites is also addressed.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155396"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160319","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
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