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Synthesis of aza- and aza-carba-pterocarpens by electrophilic amination of arene C−H bonds 芳烃C−H键亲电胺化合成氮杂和氮杂碳翼香化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-12-03 DOI: 10.1016/j.tetlet.2025.155919
Jannik Eckert, Lisa Marx, Tobias Sauter, Rafael Valentin, Andreas Speicher
{"title":"Synthesis of aza- and aza-carba-pterocarpens by electrophilic amination of arene C−H bonds","authors":"Jannik Eckert,&nbsp;Lisa Marx,&nbsp;Tobias Sauter,&nbsp;Rafael Valentin,&nbsp;Andreas Speicher","doi":"10.1016/j.tetlet.2025.155919","DOIUrl":"10.1016/j.tetlet.2025.155919","url":null,"abstract":"<div><div>Tetracyclic fused heterocycles of the aza-pterocarpen type are attracting increasing interest due to their various biological activities. We present a novel and straightforward synthesis of representative aza- and aza-carba-pterocarpens. For the first time, the Grignard-induced electrophilic amination of arene C−H bonds starting with o-nitrobiaryls was applied to this type of compound.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155919"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145681800","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 transition metal catalysis featuring Z-type ligands z型配体过渡金属催化研究进展
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-28 DOI: 10.1016/j.tetlet.2025.155909
Hikaru Takahashi, Ryo Murakami, Fuyuhiko Inagaki
{"title":"Recent advances in transition metal catalysis featuring Z-type ligands","authors":"Hikaru Takahashi,&nbsp;Ryo Murakami,&nbsp;Fuyuhiko Inagaki","doi":"10.1016/j.tetlet.2025.155909","DOIUrl":"10.1016/j.tetlet.2025.155909","url":null,"abstract":"<div><div>Z-type ligands, characterized as σ-acceptors enhancing transition metal Lewis acidity, have recently emerged as powerful tools in transition metal catalysis. Although early studies were hampered by concerns over their instability and synthetic inaccessibility, subsequent design strategies involving rigid chelating frameworks and intramolecularly stabilized p-block elements (B, Al, Ga, Sb) have overcome these challenges, thereby revitalizing interest in Z-type ligand chemistry. These ligands stabilize intermediates, lower activation barriers, and enable new catalytic pathways. Notably, Z-type ligands enhance π-acid catalysis by increasing metal electrophilicity, thereby facilitating cyclization and hydroamination reactions. They have also proven effective in selective hydrogenations and in activating otherwise unreactive bonds, including E–F (E = Si, Ge, Sn) and acyl chlorides. The development of chiral Z-type ligands based on heavier elements (Sb, Bi) has further advanced asymmetric catalysis. Computational studies have further clarified how these ligands modulate the electronic properties of the metal center, influencing both reactivity and selectivity. This review summarizes recent progress in the development and application of Z-type ligands, highlighting their growing impact on modern synthetic chemistry.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155909"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145681802","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
Additive-, thiol-, and transition-metal-free thioesterification of polyfluoroarenes in water 多氟芳烃在水中无添加剂、无硫醇和无过渡金属的硫代酯化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-21 DOI: 10.1016/j.tetlet.2025.155906
Ziyue Zhang , Mengqin Liu , Tao Qin , Heye Zhou , Bin Liu
{"title":"Additive-, thiol-, and transition-metal-free thioesterification of polyfluoroarenes in water","authors":"Ziyue Zhang ,&nbsp;Mengqin Liu ,&nbsp;Tao Qin ,&nbsp;Heye Zhou ,&nbsp;Bin Liu","doi":"10.1016/j.tetlet.2025.155906","DOIUrl":"10.1016/j.tetlet.2025.155906","url":null,"abstract":"<div><div>We report an additive-free, thiol-free, and transition-metal-free thioesterification of polyfluoroarenes that uses potassium sulfide (K₂S) and acyl chlorides under operationally simple, one-flask conditions. In neat water, K₂S engages polyfluoroarenes in a defluorinative S<sub>N</sub>Ar to generate polyfluoroaryl sulfide anions (Ar<img>S<sup><img></sup>) in situ, which are rapidly captured by acyl chlorides to afford the corresponding thioesters with high chemoselectivity, broad functional-group tolerance, and straightforward gram-scale scalability. The protocol accommodates diverse polyfluoroarene scaffolds alongside aliphatic, aromatic, and heteroaryl acyl chlorides, enabling late-stage functionalization of sensitive molecules. The applicability of this polyfluoroaryl thioester is demonstrated by its utility as a notably more reactive acylating agent relative to conventional thioesters. This platform provides a practical, concise, and scalable route to polyfluoroaryl thioesters and expands the scope of defluorinative C<img>F functionalization in water.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155906"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616502","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
Skleton rearrangement to prepare spirooxindolequinazolone 骨架重排制备螺呋辛多喹那唑酮
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-21 DOI: 10.1016/j.tetlet.2025.155899
Jiting Song , Xianheng Wang , Mingyun Liu , Changkuo Zhao
{"title":"Skleton rearrangement to prepare spirooxindolequinazolone","authors":"Jiting Song ,&nbsp;Xianheng Wang ,&nbsp;Mingyun Liu ,&nbsp;Changkuo Zhao","doi":"10.1016/j.tetlet.2025.155899","DOIUrl":"10.1016/j.tetlet.2025.155899","url":null,"abstract":"<div><div>A series of novel spirooxindole quinazolones were designed and synthesized in high yields by a two-step procedure from substituted evodiamine derivatives. The structure of obtained target compounds were identified by <sup>1</sup>H NMR, <sup>13</sup>C NMR, HRMS and X-ray spectrum.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155899"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145555290","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
Urea-promoted simple and efficient synthesis of diverse and densely functionalized 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) in aqueous ethanol 尿素促进了4,4′-（芳基亚甲基）双（1h -吡唑-5-醇）在乙醇水溶液中的简单高效合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-12-04 DOI: 10.1016/j.tetlet.2025.155921
Selvaraj Mangalaraj , Suresh Rajamanickam , Kavin Loganathan , Suhesh Aseervatham , Rashinikumar Samandram , Parthiban Anaikutti
{"title":"Urea-promoted simple and efficient synthesis of diverse and densely functionalized 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) in aqueous ethanol","authors":"Selvaraj Mangalaraj ,&nbsp;Suresh Rajamanickam ,&nbsp;Kavin Loganathan ,&nbsp;Suhesh Aseervatham ,&nbsp;Rashinikumar Samandram ,&nbsp;Parthiban Anaikutti","doi":"10.1016/j.tetlet.2025.155921","DOIUrl":"10.1016/j.tetlet.2025.155921","url":null,"abstract":"<div><div>Urea-promoted, efficient and green methodology has been developed for the synthesis of a library of medicinally relevant 4,4′-(arylmethylene)bis(1<em>H</em>-pyrazol-5-ols) moieties using aromatic aldehydes and 3-methyl-1-phenyl-2-pyrazoline-5-one in good to excellent yield. This reaction displays broad functional group tolerance and affords a cost-effective, readily available, water-soluble and environmentally safe catalyst protocol for the quick synthesis of 4,4′-(arylmethylene)bis(1<em>H</em>-pyrazol-5-ols) derivatives from readily available substrates. All the synthesized compounds were characterized by various analytical techniques such as FT-IR, <sup>1</sup>H (Proton) NMR, <sup>13</sup>C (Carbon) NMR analysis and high-resolution mass spectrometry.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155921"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145733300","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
Acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic/heteroaromatic ortho-aminonitriles: Diastereoselective access to polycyclic acridines and related heterocycles 2-（2-甲氧基苯基）取代环烷醇与芳香/杂芳香邻氨基腈的酸催化多米诺反应：多环吖啶和相关杂环的非对映选择性获取
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-19 DOI: 10.1016/j.tetlet.2025.155904
Yuliya S. Rozhkova, Arina S. Pegushina, Vyacheslav V. Morozov, Daria V. Eroshenko, Yurii V. Shklyaev
{"title":"Acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic/heteroaromatic ortho-aminonitriles: Diastereoselective access to polycyclic acridines and related heterocycles","authors":"Yuliya S. Rozhkova,&nbsp;Arina S. Pegushina,&nbsp;Vyacheslav V. Morozov,&nbsp;Daria V. Eroshenko,&nbsp;Yurii V. Shklyaev","doi":"10.1016/j.tetlet.2025.155904","DOIUrl":"10.1016/j.tetlet.2025.155904","url":null,"abstract":"<div><div>A novel acid-catalyzed domino reaction of 2-(2-methoxyphenyl)-substituted cycloalkanols with aromatic and heteroaromatic <em>ortho</em>-aminonitriles was developed, resulting in the diastereoselective formation of new polycyclic acridines and related heterocycles, including partially hydrogenated quinolino[4,3,2-<em>kl</em>]acridines, cyclopenta[5,6]pyrido[4,3,2-<em>kl</em>]acridine, and fused pyrido[4,3,2-<em>gh</em>]phenanthridines, in 14–81 % yields. The developed domino sequence involves initial dearomative electrophilic <em>ortho</em>-spirocyclization <em>via</em> the Ritter reaction, followed by intramolecular nucleophilic trapping of the spiro-<em>σ</em>-intermediate by the amino group and subsequent aromatization <em>via</em> [1,2]-alkyl shift. Several of the synthesized quinolino[4,3,2-<em>kl</em>]acridines showed high antibacterial activity against <em>S. epidermidis</em> ATCC 29887 and <em>M. smegmatis</em> mc<sup>2</sup> 155.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155904"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145681801","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
Synthesis of polyfunctionalized carbazole aldehydes by a [4+2] annulation of ethyl 2-(1-alkyl-3-formyl-1H-indol-2-yl)acetate with alkynals [4+2]环化2-（1-烷基-3-甲酰基- 1h -吲哚-2-基）乙酸乙酯与烷基醇合成多功能化咔唑醛
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-23 DOI: 10.1016/j.tetlet.2025.155907
Bei Wei , Meng Xue , Aining Dong , Zungan Wang , Bin Liu , Shurong Ban
{"title":"Synthesis of polyfunctionalized carbazole aldehydes by a [4+2] annulation of ethyl 2-(1-alkyl-3-formyl-1H-indol-2-yl)acetate with alkynals","authors":"Bei Wei ,&nbsp;Meng Xue ,&nbsp;Aining Dong ,&nbsp;Zungan Wang ,&nbsp;Bin Liu ,&nbsp;Shurong Ban","doi":"10.1016/j.tetlet.2025.155907","DOIUrl":"10.1016/j.tetlet.2025.155907","url":null,"abstract":"<div><div>In our study, we report a general, mild, efficient, and practical method for synthesizing polyfunctionalized carbazole aldehydes. The synthesis is achieved through a secondary amine-catalyzed Michael-Aldol reaction between ethyl 2-(1-alkyl-3-formyl-1<em>H</em>-indol-2-yl)acetate and alkynals. This method provides a powerful alternative approach to access carbazole aldehyde frameworks in moderate to good yields (60–80 %).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155907"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616501","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
H3PW12O40-catalyzed cyclization of o-aminobenzamides with ortho esters for quinazolinones synthesis h3pw12o40催化邻氨基苯酰胺与邻位酯环化合成喹唑啉酮类化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-12-13 DOI: 10.1016/j.tetlet.2025.155920
Xuejiao Chen , Wenqing Luo , Zhibin Zhang , Yufeng Liu , Yalin Zhang , Guoping Yang
{"title":"H3PW12O40-catalyzed cyclization of o-aminobenzamides with ortho esters for quinazolinones synthesis","authors":"Xuejiao Chen ,&nbsp;Wenqing Luo ,&nbsp;Zhibin Zhang ,&nbsp;Yufeng Liu ,&nbsp;Yalin Zhang ,&nbsp;Guoping Yang","doi":"10.1016/j.tetlet.2025.155920","DOIUrl":"10.1016/j.tetlet.2025.155920","url":null,"abstract":"<div><div>This study presents an efficient and environmentally benign protocol for the synthesis of quinazolinones via H<sub>3</sub>PW<sub>12</sub>O<sub>40</sub>-catalyzed cyclization of <em>o</em>-aminobenzamides with <em>ortho</em> esters under mild conditions. By employing H<sub>3</sub>PW<sub>12</sub>O<sub>40</sub> as the catalyst and EtOH as the solvent, various <em>o</em>-aminobenzamides and <em>ortho</em> esters reacted efficiently to form quinazolinones up to 96 % yield. The advantages of this transformation include the use of a green catalyst and solvent, a broad substrate scope, high efficiency, and operational simplicity. This strategy would provide opportunities for the green synthesis of potential biologically active molecules.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155920"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145733298","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
The reaction of 4-nitro-5-styrylisoxazoles and indoline 4-硝基-5-苯乙烯基异恶唑与吲哚的反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-12-08 DOI: 10.1016/j.tetlet.2025.155925
Simone Bruschi , Lucio Leopaldi , Erica Paltrinieri , Mauro F.A. Adamo
{"title":"The reaction of 4-nitro-5-styrylisoxazoles and indoline","authors":"Simone Bruschi ,&nbsp;Lucio Leopaldi ,&nbsp;Erica Paltrinieri ,&nbsp;Mauro F.A. Adamo","doi":"10.1016/j.tetlet.2025.155925","DOIUrl":"10.1016/j.tetlet.2025.155925","url":null,"abstract":"<div><div>An unprecedented 1,6 conjugate addition of aza-nucleophile indoline to 4-nitro-5-styrylisoxazoles is reported. Selected adducts, which were obtained in high yields, were subsequently converted to the corresponding β-indolinecarboxylates via the hydrolysis of the 4-nitroisoxazole core. The synthetic methodology, herein described, provides access to indoline-beta carboxylic acids and their esters which synthesis has been rarely reported.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155925"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145733301","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
The base-promoted one-pot reaction of dichloronaphthoquinone and aryl methylamine with S8 to construct naphtho[2,3-d]thiazole 碱促二氯萘醌和芳基甲胺与S8反应生成萘[2,3-d]噻唑
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-24 DOI: 10.1016/j.tetlet.2025.155882
Pei-Lin Qi, Chen-Xi Huang, Yu-Jin Li
{"title":"The base-promoted one-pot reaction of dichloronaphthoquinone and aryl methylamine with S8 to construct naphtho[2,3-d]thiazole","authors":"Pei-Lin Qi,&nbsp;Chen-Xi Huang,&nbsp;Yu-Jin Li","doi":"10.1016/j.tetlet.2025.155882","DOIUrl":"10.1016/j.tetlet.2025.155882","url":null,"abstract":"<div><div>The coupling reaction between 2,3-dichloro-1,4-naphthoquinone, benzylamine, and S<sub>8</sub> affords 2-aryl-substituted naphtho[2,3-<em>d</em>]thiazole-4,9-diones. This approach to the naphtho[2,3-<em>d</em>]thiazole ring had the advantages of inexpensive raw materials, no transition metals, and economic efficiency. A nucleophilic addition to C2 and C3 of dichloro-1,4-naphthoquinone was proposed for this conversion.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155882"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616430","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
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