IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-10 DOI: 10.1016/j.tet.2026.135185

Shiyun Li , Yu Chen , Yan An , Yong Ou , Jun Huang , Bin Wen , Yuanqing Dong , Tiesen Li , Xingquan Chen

引用次数: 0

Cyclization of 2-phenylglycines and ortho-substituted nitroarenes to access pyrrolo[1,2-a]quinoxalines, quinazolines, and quinazolinone promoted by activated carbon 活性炭促进2-苯基甘氨酸和邻取代硝基芳烃环化得到吡咯[1,2-a]喹诺啉、喹唑啉和喹唑啉酮

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-08 DOI: 10.1016/j.tet.2026.135184

Hao Tien Tran , Y Ngoc Nhu Huynh , Duyen Khanh Nguyen , Khanh Thi Ngoc Ong , Anh Thai Nguyen , Thanh-Lam Bui , Štĕpán Kment , Ngoc Do Quyen Chau , Tung Thanh Nguyen

{"title":"Cyclization of 2-phenylglycines and ortho-substituted nitroarenes to access pyrrolo[1,2-a]quinoxalines, quinazolines, and quinazolinone promoted by activated carbon","authors":"Hao Tien Tran , Y Ngoc Nhu Huynh , Duyen Khanh Nguyen , Khanh Thi Ngoc Ong , Anh Thai Nguyen , Thanh-Lam Bui , Štĕpán Kment , Ngoc Do Quyen Chau , Tung Thanh Nguyen","doi":"10.1016/j.tet.2026.135184","DOIUrl":"10.1016/j.tet.2026.135184","url":null,"abstract":"<div><div>Derivatives of 2-phenylglycine are activated in the presence of commercial activated carbon, providing a benzyl synthon to couple with <em>ortho</em>-nitro substituted derivatives of <em>N</em>-pyrroles, benzaldehyde oximes, and benzamide to furnish pyrrolo[1,2-<em>a</em>]quinoxalines, quinazolines, and quinazolinone respectively. Reactions did not require any further additives such as metal complex, acid, or base. An array of useful <em>N</em>,<em>N</em>-based heterocycles were isolated in good yields. The spent carbon after synthesis of pyrrolo[1,2-<em>a</em>]quinoxaline was collected and characterized by X-ray photoelectron spectroscopy (XPS), thermogravimetry analysis (TGA), nitrogen sorption isotherms, X-ray diffraction (XRD), Raman spectroscopy, Fourier-transform infrared spectroscopy (FT-IR), and scanning electronic microscopy (SEM). The characteristic results revealed that while adsorption of product as well as unreacting starting materials could occur, structural integrity of the carbon was mainly recovered. Our method features a convenient, sustainable pathway to achieve synthetically useful heterocyles from α-amino acids in the absence of metal- or any other specific additives.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"194 ","pages":"Article 135184"},"PeriodicalIF":2.2,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146186111","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

Efficient photochemical synthesis of unsymmetrical ureas through aerobic oxidative desulfurization using a CdS/NH2-MIL-125 photocatalyst 利用CdS/NH2-MIL-125光催化剂，通过好氧氧化脱硫高效光化学合成不对称尿素

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-01-17 DOI: 10.1016/j.tet.2026.135148

Saeede Saki , Mina Tavakolian , Mona Hosseini-Sarvari

引用次数: 0

Mechanofluorochromic properties of 1,5-diphenylanthracene derivatives 1,5-二苯镧衍生物的机械荧光特性

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-02 DOI: 10.1016/j.tet.2026.135171

Manato Nishimura , Fumihiro Kannen , Kenji Yoza , Takahiro Kusukawa

{"title":"Mechanofluorochromic properties of 1,5-diphenylanthracene derivatives","authors":"Manato Nishimura , Fumihiro Kannen , Kenji Yoza , Takahiro Kusukawa","doi":"10.1016/j.tet.2026.135171","DOIUrl":"10.1016/j.tet.2026.135171","url":null,"abstract":"<div><div>Several 1,5-diphenylanthracene derivatives <strong>1</strong>–<strong>4</strong> were prepared and their photophysical properties were observed in the both solution and solid states. Interestingly, the fluorine-group-substituted 1,5-diphenylanthracene derivatives <strong>1e</strong> (R=F), <strong>2e</strong> (R=F), <strong>3</strong> (3,5-F<sub>2</sub>) and Me-substituted derivative <strong>1b</strong> (R = Me) were found to exhibit higher fluorescence quantum yield (<em>ϕ</em><sub>f</sub> = 0.75–0.93) in the solid state than in the solution state (<em>ϕ</em><sub>f</sub> = 0.53–0.57), causing “crystallization induced emission enhancement”. For the 1,5-diphenylanthracene derivatives <strong>1a</strong> (R=H), <strong>1d</strong> (R=CF<sub>3</sub>), <strong>1e</strong> (R=F), <strong>1f</strong> (R=CN) and <strong>2e</strong> (3-F), the luminous color change from the “bluish” to “greenish” color was observed after grinding under 365 nm UV light. Additionally, the reversible luminous color changes were also observed for the “grinding-heating” and “grinding-fuming (with solvent vapor)” processes. Furthermore, luminous color change from the ground “green” luminous color to the “blue” luminous color was observed upon 365 nm UV irradiation, and successfully demonstrated the “writing-erasing” cycle of the character writings using the “grinding-UV irradiation” process toward security writing.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"194 ","pages":"Article 135171"},"PeriodicalIF":2.2,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146185789","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

From flavones to flavanols: An enzymatic kinetic resolution approach to enantioenriched 2-(het)arylchroman-4-ols 从黄酮到黄烷醇：富含对映体的2-（二）芳基铬-4醇的酶动力学分解方法

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-02 DOI: 10.1016/j.tet.2026.135174

Oleksii S. Timokhin , Vladyslav V. Hys , Olexandr V. Kucher , Andrii V. Kozytskyi , Roman V. Yizhak , Volodymyr S. Brovarets , Oleksandr O. Grygorenko , Viktoriia S. Moskvina

引用次数: 0

Polydopamine: A bioinspired catalyst for the metal-free synthesis of quinazolinones using DMSO as a carbon synthon 聚多巴胺：一种以二甲基亚砜为碳合成物的无金属合成喹唑啉酮的生物催化剂

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-01-23 DOI: 10.1016/j.tet.2026.135158

Shweta A. Pawar, A. Vijay Kumar

{"title":"Polydopamine: A bioinspired catalyst for the metal-free synthesis of quinazolinones using DMSO as a carbon synthon","authors":"Shweta A. Pawar, A. Vijay Kumar","doi":"10.1016/j.tet.2026.135158","DOIUrl":"10.1016/j.tet.2026.135158","url":null,"abstract":"<div><div>Polydopamine (PDA) is demonstrated as a promising heterogeneous organocatalyst for the efficacious synthesis of quinazolin-4(3<em>H</em>)-ones employing the readily available DMSO as the methine synthon. PDA-mediated activation of DMSO in the presence of the green oxidant molecular oxygen, facilitated oxidative annulation of anthranilamides to afford quinazolin-4(3<em>H</em>)-one frameworks. This method enabled a broad substrate scope, with various anthranilamide derivatives and sulfoxide precursors furnishing the corresponding quinazolin-4(3<em>H</em>)-ones products in good to excellent yields. The mechanistic studies revealed an oxygen-mediated radical pathway for quinazolin-4(3<em>H</em>)-ones synthesis. The developed protocol was robustly applied to the synthesis of the bioactive alkaloid (Z)-schizocommunin and the CNS depressant drug methaqualone. PDA was efficiently recovered and recycled for up to three consecutive cycles for the quinazolin-4(3<em>H</em>)-ones reaction. Overall, the developed PDA-mediated protocol delivered notable advantages, including metal-free conditions, catalyst recyclability, and the avoidance of additives, co-catalysts, and peroxides, underscoring the utility of PDA as a heterogeneous organocatalyst for oxidative annulation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"194 ","pages":"Article 135158"},"PeriodicalIF":2.2,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146071018","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

Visible-light-promoted regioselective C5–H selenylation of pyrrolo[2,3-d] pyrimidine derivatives with diorganyldiselenides 可见光促进吡咯[2,3-d]嘧啶衍生物与二有机基二硒化物的C5-H选择性硒化反应

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-06 DOI: 10.1016/j.tet.2026.135175

Zixuan Liu , Mingrui Liu , Yaorong Liu, Jiaqi Tong, Xingxian Zhang

引用次数: 0

A sequence of cross-coupling and deprotection reactions of 13-methoxy-15-aryl(hetaryl)-11,13-dihydroisoalantolactone derivatives to access a library of a ring substituted eudesmane type methylenelactones. Cytotoxicity studies 13-甲氧基-15-芳基（己基）-11,13-二氢异丙酸内酯衍生物的一系列交叉偶联和脱保护反应获得了一个环取代的德士曼型亚甲基内酯文库。细胞毒性研究

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-02 DOI: 10.1016/j.tet.2026.135173

Sergey S. Patrushev, Tatyana V. Rybalova, Yulia V. Meshkova, Mariya K. Marenina, Tatyana G. Tolstikova, Elvira E. Shults

{"title":"A sequence of cross-coupling and deprotection reactions of 13-methoxy-15-aryl(hetaryl)-11,13-dihydroisoalantolactone derivatives to access a library of a ring substituted eudesmane type methylenelactones. Cytotoxicity studies","authors":"Sergey S. Patrushev, Tatyana V. Rybalova, Yulia V. Meshkova, Mariya K. Marenina, Tatyana G. Tolstikova, Elvira E. Shults","doi":"10.1016/j.tet.2026.135173","DOIUrl":"10.1016/j.tet.2026.135173","url":null,"abstract":"<div><div>The eudesmane-type sesquiterpene lactone isoalantolactone is of significant interest due to its biological activity and synthetic application. A convenient and effective methodology for synthesizing a library of new chiral 15-aryl(hetaryl)-substituted derivatives of isoalantolactone was developed. All compounds were obtained with a moderate preparative yield upon consecutive cross-coupling reaction of 13-methoxy-11,13-dihydroisoalantolactones with aryl(hetaryl)halides and deprotection of the formed 15-aryl(hetaryl)-13-methoxy-11,13-dihydroisoalantolactones. The effectiveness of Pd(OAc)<sub>2</sub> – Ag<sub>2</sub>CO<sub>3</sub> catalytic system has been demonstrated in the Mizoroki-Heck reaction (yield 56–95%). Additionally 15-aryl-4,15-epoxyisoalantolactone derivatives and 15-aryl-4,15-(<em>gem</em>-difluorocyclopropane)isoalantolactones were prepared (yield 58–60%). A retro-Michael reaction of (11<em>R</em>)- and (11<em>S</em>)-stereoisomeric 15-substituted 13-methoxy-11,13-dihydroisoalantolactones using cesium carbonate in DMF led to 15-substituted isoalantolactone derivatives (yield 40–87%). Chemical structure of new compounds was determined using a complex of spectroscopic methods and X-ray diffraction analysis. Biological evaluation of these semisynthetic sesquiterpene lactone derivatives (MTT assay) in HepG2 and MCF 7 cancer cells showed interesting antiproliferative profiles and provided initial structure−activity data.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"194 ","pages":"Article 135173"},"PeriodicalIF":2.2,"publicationDate":"2026-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146185794","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-diaryl-5,6-dihydropyrrolo[2,1-a] isoquinolines via copper-promoted reaction of tetrahydroisoquinolines with α,β-unsaturated ketones under solvent-free conditions 铜促进四氢异喹啉与α，β-不饱和酮在无溶剂条件下反应合成1,3-二芳基-5,6-二氢吡咯[2,1-a]异喹啉

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-05 DOI: 10.1016/j.tet.2026.135178

Huacan Xu , Ke Zhang , Linglong Zhang , Yanjing Zhang , Jinwei Sun , Yuling Li , Yun Liu

引用次数: 0

Asymmetric syntheses of two Enantiomers of the sex pheromone component of smaller tea tortrix moth 小型茶蛾性信息素成分两种对映体的不对称合成

IF 2.2 3区化学

Tetrahedron Pub Date : 2026-06-01 Epub Date: 2026-02-03 DOI: 10.1016/j.tet.2026.135179

Zhi-Feng Sun , Yi-Fan Li , Miao Li , Hai-Long Zhou , Jian-Li Zhao , Li-Hua Li , Qiang Zhang , Ling-Xia Jin , Cun-Fang Liu , Guang-Hui Tian , Xiao-Hui Ji , Zhi-Qiang Zhang

引用次数: 0

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