Tetrahedron最新文献

tert-Butyl peroxybenzoate (TBPB)-mediated copper-catalyzed C(sp3)-H methylation of 4-thiazolidinone

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-15 DOI: 10.1016/j.tet.2025.134590

Rajnikant N. Ghoghari, Anant R. Patel, Kishor H. Chikhalia

引用次数: 0

Sustainable magnetic ZnFe2O4 Nanoparticles as a Potent heterogeneous catalyst for the synthesis of phenols and nitroarenes

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-14 DOI: 10.1016/j.tet.2025.134582

Amar Jyoti Kalita, Aquif Suleman, Jyotismita Bora, Mayuri Dutta, Bolin Chetia

{"title":"Sustainable magnetic ZnFe2O4 Nanoparticles as a Potent heterogeneous catalyst for the synthesis of phenols and nitroarenes","authors":"Amar Jyoti Kalita, Aquif Suleman, Jyotismita Bora, Mayuri Dutta, Bolin Chetia","doi":"10.1016/j.tet.2025.134582","DOIUrl":"10.1016/j.tet.2025.134582","url":null,"abstract":"<div><div>This work primarily focuses on the biogenic synthesis of ZnFe<sub>2</sub>O<sub>4</sub> nanoparticles using <em>Lantana camara</em> leaf extract. The material features a spherical morphology as confirmed from SEM and HRTEM analysis of the material. The material is explored as a heterogeneous catalyst in the synthesis of phenols and nitroarenes from phenyl Boronic acids. The synthesis and catalytic protocol are highly sustainable and apply to a wide range of substrates with excellent yield of products in a very short reaction time and is more advantageous than recently published works in terms of temperature, time and amounts of oxidant used. For the first time we have reported a Zn based nano catalysts for such important organic transformations. The structural and compositional characteristics of the material were studied through SEM, HRTEM, PXRD, EDX, and XPS. The ferromagnetic behaviour of the material was also confirmed with VSM which facilitates the efficient recovery of the material. Our finding exhibits an efficient approach not only for the synthesis of ZnFe<sub>2</sub>O<sub>4</sub> NPs but also for its application as a heterogeneous catalyst.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"178 ","pages":"Article 134582"},"PeriodicalIF":2.1,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644751","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

Selective oxidation of aromatic olefins to aldehydes with hydrogen peroxide over V-ZSM-5 catalyst

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-13 DOI: 10.1016/j.tet.2025.134592

Xuewei Xu, Jiaming Guo, Yaya Wang, Shunli Du, Xinyue Zhang, Xinhua Peng

引用次数: 0

Synthesis and antinociceptive activity of long-known but unexplored nitro-fentanyl derivatives

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-13 DOI: 10.1016/j.tet.2025.134591

Ivana I. Jevtić , Sonja M. Vučković , Dragana P. Srebro , Katarina R. Savić Vujović , Slađana V. Kostić-Rajačić , Milovan D. Ivanović

{"title":"Synthesis and antinociceptive activity of long-known but unexplored nitro-fentanyl derivatives","authors":"Ivana I. Jevtić , Sonja M. Vučković , Dragana P. Srebro , Katarina R. Savić Vujović , Slađana V. Kostić-Rajačić , Milovan D. Ivanović","doi":"10.1016/j.tet.2025.134591","DOIUrl":"10.1016/j.tet.2025.134591","url":null,"abstract":"<div><div>Fentanyl and related 4-anilidopiperidines are the most potent and clinically important analgesics for the treatment of severe acute and chronic pain. Many fentanyl derivatives have been made so far to obtain new analgesics with improved pharmacological profile. However, of simple nitro fentanyl derivatives only the <em>meta</em> isomer was reported, while <em>ortho</em> and <em>para</em> isomers proved to be synthetically challenging. We report here for the first time the synthesis of <em>ortho</em> and <em>para</em>-nitro-fentanyl. The most arduous step in the synthesis was the acylation of nitroaniline precursor, where the <em>ortho</em> and <em>para</em> positioned nitro group with strong electron-withdrawing and/or steric effects led to an extremely low nucleophilicity of anilino nitrogen. To address this problem electrophilic conditions had to be enhanced using strong acylating agent i.e. propionyl chloride or bromide, and bases such as Et<sub>3</sub>N or pyridine in a polar, aprotic solvent such as <em>N</em>,<em>N</em>-dimethylformamide (DMF). Indeed, under these conditions, acylation step afforded title products in excellent yields. The <em>in vivo</em> pharmacological evaluation demonstrated that regioisomerism plays a role in the potency and the onset of action of these compounds. The <em>ortho</em>-nitro derivative emerged as the most effective analgesic, exhibiting approximately 50 times less potency than fentanyl, comparable to morphine. Furthermore, it demonstrated a faster onset of action than fentanyl while maintaining a similar duration of effect. These traits indicate that it may be well-suited for treating severe acute pain and breakthrough pain in chronic pain conditions. <em>Ortho</em>-nitro fentanyl is henceforth worthy of further evaluation in toxicity and safety pharmacology studies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134591"},"PeriodicalIF":2.1,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143631942","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

The photochemical isomerization of 2-picoline N-oxide, 4,6-dimethylpyrimidine N-oxide and 2-methoxypyrimidine N-oxide. A DFT study

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-12 DOI: 10.1016/j.tet.2025.134583

Maurizio D'Auria, Rocco Racioppi

引用次数: 0

One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-12 DOI: 10.1016/j.tet.2025.134589

Igor Yu Grishin, Dmitrii A. Aksenov, Nicolai A. Aksenov, Yuriy I. Grishin, Alexander V. Leontiev, Alexander V. Aksenov

引用次数: 0

Nitrogen-containing polydentate ligand with –NR3+/−PPh3+ moieties chelated Pd(0) nanoparticles functionalized fiber for green catalysis of C–C bond coupling reaction

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-11 DOI: 10.1016/j.tet.2025.134586

Kun Yue, Ying Yuan, Haoyu Dong, Lu Wang, Bo Ren, Guiqin Lou, Jian Xiao

{"title":"Nitrogen-containing polydentate ligand with –NR3+/−PPh3+ moieties chelated Pd(0) nanoparticles functionalized fiber for green catalysis of C–C bond coupling reaction","authors":"Kun Yue, Ying Yuan, Haoyu Dong, Lu Wang, Bo Ren, Guiqin Lou, Jian Xiao","doi":"10.1016/j.tet.2025.134586","DOIUrl":"10.1016/j.tet.2025.134586","url":null,"abstract":"<div><div>Highly dispersion and small particle size Pd(0) nanoparticles were immobilized into nitrogen-containing polydentate ligand and quaternary ammonium/phosphonium salt bifunctionalized polyacrylonitrile fiber to prepared a novel functionalized fiber catalyst (PAN<sub>NP/QA&PS</sub>F-Pd(0)). Some necessary instrumental analysis methods, including inductively coupled plasma atomic emission spectroscopy (ICP-AES), X-ray photoelectron spectroscopy (XPS), Transmission Electron Microscope (TEM), etc., were applied to accurately characterize the microscopic physical and chemical properties of PAN<sub>NP/QA&PS</sub>F-Pd(0), confirming the structure of the novel fiber catalyst was in accordance with our expected design. Additionally, the Heck reaction was changed as a classic template reaction for evaluating the catalytic activity of prepared fiber catalyst. The result verified that PAN<sub>NP/QA&PS</sub>F-Pd(0) can efficiently catalyze the Heck reaction between different halogenated aromatic hydrocarbons and terminal olefins within 6 h under catalyst dosage of 0.02 % and solvent-free condition, and the isolated yields of target products can reach 46–99 %, respectively. Furthermore, PAN<sub>NP/QA&PS</sub>F-Pd(0) can also smoothly catalyze Suzuki reaction between different iodized aromatics and arylboric acids, achieving satisfactory yields of 67–99 %. Moreover, PAN<sub>NP/QA&PS</sub>F-Pd(0) can be reused 8 times with slight decline in catalytic activity (isolated yield of 91 % and 80 %, respectively), and the average size of Pd(0) nanoparticles only increased from 1.94 nm to 2.98 nm, verifing that the Pd(0) nanoparticles in PAN<sub>NP/QA&PS</sub>F-Pd(0) was validly dispersed and stabilized, which makes the fiber catalyst has excellent recyclability. Noteworthily, a reasonable heterogeneous catalytic mechanism was proposed.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134586"},"PeriodicalIF":2.1,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628139","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

Bidentate deltamide hydrogen bond donor catalyzed cycloaddition of carbon dioxide into epoxide

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-11 DOI: 10.1016/j.tet.2025.134587

Chunyu Li, Yujia Wang, Zhenjiang Li, Ling Li, Min Zhang, Yanqi Shi, Yue Xu, Xin Zou, Xin Yuan, Kai Guo

{"title":"Bidentate deltamide hydrogen bond donor catalyzed cycloaddition of carbon dioxide into epoxide","authors":"Chunyu Li, Yujia Wang, Zhenjiang Li, Ling Li, Min Zhang, Yanqi Shi, Yue Xu, Xin Zou, Xin Yuan, Kai Guo","doi":"10.1016/j.tet.2025.134587","DOIUrl":"10.1016/j.tet.2025.134587","url":null,"abstract":"<div><div>The cycloaddition of carbon dioxide into epoxides through hydrogen bond donor (HBD) and halide nucleophile as a binary catalyst to afford cyclic carbonates has become a key strategy for fixing carbon dioxide. A series of bidentate HBD catalysts of deltamides featured with N–H bond were synthesized and evaluated in the cycloaddition of CO<sub>2</sub> to epoxides (CCE) reactions. The influences on the catalytic activity were scrutinized, which included tunable substituents, types of nucleophiles, reaction time, temperature and the loading of the catalyst. The HBD catalyst 2,3-bis((4-(trifluoromethyl)phenyl)amino)cycloprop-2-en-1-one (DT3) with substituted –CF<sub>3</sub> group in combination with tetrabutylammonium iodide (NBu<sub>4</sub>I) showed the best performance with 95 % conversion of styrene oxide into cyclic carbonate under mild conditions (0.1 MPa, 100 °C and 12 h). Substrate applicability of the catalyst is illustrated by the conversion of quantity terminal epoxides with excellent yields and quantitative selectivity. <sup>1</sup>H NMR titration spectra and control studies were employed to probe a reasonable activation mechanism of the cycloaddition of CO<sub>2</sub> to epoxides reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"177 ","pages":"Article 134587"},"PeriodicalIF":2.1,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628138","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

Cascade C(sp3)-H bond functionalization/cyclization reaction for the synthesis of 3,3-disubstituted oxindoles by decatungstate photocatalysis

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-11 DOI: 10.1016/j.tet.2025.134578

Xianhe Fang , Jiaxing Lv , Shuxin Yang , Mingyu Ma , Runzhe Yang , Yi Bi

引用次数: 0

Isolation, characterization, and biological activities of halogenated sesquiterpenes and C15 acetogenins from the Okinawan sea hare, Aplysia argus

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-03-10 DOI: 10.1016/j.tet.2025.134588

Ryunosuke Nakamura , Koushi Matsuyama , Naomichi Arima , Fumito Tani , Satoaki Onitsuka , Hiroaki Okamura , Tetsuo Iwagawa , Masayuki Sudoh , Toshiyuki Hamada

引用次数: 0