TetrahedronPub Date : 2025-04-24DOI: 10.1016/j.tet.2025.134681
Alfredo Vazquez , Guillermo Delgado-Lamas , Luis D. Miranda
{"title":"Organic chemistry in Mexico at a glance","authors":"Alfredo Vazquez , Guillermo Delgado-Lamas , Luis D. Miranda","doi":"10.1016/j.tet.2025.134681","DOIUrl":"10.1016/j.tet.2025.134681","url":null,"abstract":"","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"181 ","pages":"Article 134681"},"PeriodicalIF":2.1,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143941278","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}
TetrahedronPub Date : 2025-04-24DOI: 10.1016/j.tet.2025.134678
Priya C. Saroj , Manjunath S. Lokolkar , Sai Srinivas Ponugoti , Priyanka R. Ugale , Bhalchandra M. Bhanage , Shreerang V. Joshi
{"title":"Nickel/aluminium oxide as a sustainable and cost-effective catalyst for the Sonogashira coupling reaction","authors":"Priya C. Saroj , Manjunath S. Lokolkar , Sai Srinivas Ponugoti , Priyanka R. Ugale , Bhalchandra M. Bhanage , Shreerang V. Joshi","doi":"10.1016/j.tet.2025.134678","DOIUrl":"10.1016/j.tet.2025.134678","url":null,"abstract":"<div><div>In our study, we report a cost-effective and sustainable Sonogashira coupling reaction with Nickel supported on alumina (Ni/Al<sub>2</sub>O<sub>3</sub>) as a palladium-free catalyst. The procedure effectively couples phenylacetylene and 2-ethynylpyridine with various aryl iodides under optimized conditions and provides a greener route by reducing hazardous waste, cost-effectiveness, and eliminating toxic palladium catalysts. The simplicity of catalyst preparation and reusability of the catalyst make the procedure amenable to large-scale applications in keeping with green chemistry principles.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134678"},"PeriodicalIF":2.1,"publicationDate":"2025-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144138303","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}
{"title":"An overview of the synthesis of biheterocyclic compounds featuring four-membered rings containing nitrogen, oxygen, or sulfur","authors":"Soumyadip Das , Badruzzaman Choudhury , Sameer Chauhan , M.M. Balamurali , Kaushik Chanda","doi":"10.1016/j.tet.2025.134679","DOIUrl":"10.1016/j.tet.2025.134679","url":null,"abstract":"<div><div>Biheterocyclic compounds with Four-membered rings are crucial in medicinal chemistry due to their ability to incorporate diverse functional groups, enhancing drug efficacy and selectivity. Their unique frameworks provide opportunities for developing innovative therapeutic agents. In this review, we have discussed the various synthetic protocols for the syntheses of four membered heterocycles consist with linked, spiro, fused heterocyclic compounds. This study provides a comprehensive analysis of the latest synthetic methodologies developed to overcome existing limitations and challenges in the preparation of biheterocyclic derivatives featuring four-membered rings. It emphasizes the importance of addressing issues such as ring strain, selectivity, and scalability while highlighting innovative approaches that pave the way for more efficient and sustainable synthesis. The focus is directed toward the biological significance of these derivatives, showcasing their potential as valuable frameworks in the discovery and development of novel therapeutic agents.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"181 ","pages":"Article 134679"},"PeriodicalIF":2.1,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143879291","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}
{"title":"Total synthesis of quasi-symmetric dihydrofuran lignans (−)-ribesin A and B isolated from Ribes nigrum leaves","authors":"Kae Horio , Hayato Maeda , Kayo Horie , Naoki Nanashima , Ken-ichi Nihei","doi":"10.1016/j.tet.2025.134675","DOIUrl":"10.1016/j.tet.2025.134675","url":null,"abstract":"<div><div>Dihydrofuran lignans ribesin A (<strong>1</strong>) and ribesin B (<strong>2</strong>) isolated from <em>Ribes nigrum</em> leaves were chemically synthesized for the first time using oxa-Michael addition–carbocyclization and double-bond migration as key steps. However, the NMR data of synthesized ribesin B (<strong>2</strong>) with vanillin scaffolds were slightly inconsistent with those of reported ribesin B (<strong>2</strong>). Through further synthetic study, the structure of natural ribesin B (<strong>2</strong>) was revised to that of <strong>3</strong>, which has unique isovanillin scaffolds. Moreover, the asymmetric total synthesis of natural products ribesin A (<strong>1</strong>) and ribesin B (<strong>3</strong>) was achieved using chiral propargyl alcohols as the starting materials prepared <em>via</em> lipase-catalyzed kinetic resolution.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"181 ","pages":"Article 134675"},"PeriodicalIF":2.1,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143879290","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}
{"title":"TfOH-catalyzed PPh3-promoted nucleophilic cyclization reactions for the synthesis of functionalized (Z)-2-imino-benzo[e][1,3]thiazin-4-ones","authors":"Lirong Jiang, Jiayang Zhang, Xiaolu Li, Xuan Tang, Shuwen Gong, Xianqiang Huang, Guodong Shen","doi":"10.1016/j.tet.2025.134676","DOIUrl":"10.1016/j.tet.2025.134676","url":null,"abstract":"<div><div>The first example of an effective TfOH-catalyzed PPh<sub>3</sub>-promoted nucleophilic cyclization reaction for the synthesis of (<em>Z</em>)-2-imino-benzo[<em>e</em> ][1,3]thiazin-4-ones <em>via</em> benzo [<em>c</em>] [1,2]dithiol-3-ones and carbodiimides have been developed. The nucleophilic cyclization reaction offers new concise routes to access various functionalized (<em>Z</em>)-2-imino-benzothiazinones in moderate to excellent yields under mild reaction conditions, which are of biological and synthetic importance.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134676"},"PeriodicalIF":2.1,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858836","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}
TetrahedronPub Date : 2025-04-21DOI: 10.1016/j.tet.2025.134677
Salehe Sabouri , Fatemeh Haghani , Mohammad Amin Langarizadeh , Mehdi Abaszadeh
{"title":"Synthesis, molecular modeling, cytotoxicity, and apoptosis-inducing activity of some novel 4,6-dihydroisothiochromeno[4,3-b]pyran derivatives as potent anticancer and tubulin-inhibiting agents","authors":"Salehe Sabouri , Fatemeh Haghani , Mohammad Amin Langarizadeh , Mehdi Abaszadeh","doi":"10.1016/j.tet.2025.134677","DOIUrl":"10.1016/j.tet.2025.134677","url":null,"abstract":"<div><div>Thiochromene analogs are known for a broad spectrum of remarkable biological and pharmacological activities such as anticancer. In this study, a series of new 4,6-dihydroisothiochromeno[4,3-<em>b</em>]pyran compounds have been synthesized, and their cytotoxicity of these compounds was evaluated on two cancer cell lines by MTT assay. Compounds <strong>4b</strong>, <strong>4d</strong>, <strong>4e</strong>, <strong>4g</strong>, <strong>4j</strong>, <strong>4m</strong>, and <strong>4n</strong> showed the most potent cytotoxic activity (IC<sub>50</sub> values less than 110 μM) on the MCF-7 cell line. These compounds' ability to induce apoptosis in MCF-7 cells was analyzed by flow cytometry, and all the compounds could lead the cell's fate to apoptosis. During the computational study of these compounds, several potential targets were identified, and subsequent molecular docking experiments revealed that tubulin inhibition could provide a plausible mechanism for their effectiveness. Tubulin, a key structural protein involved in the formation of microtubules, plays a crucial role in processes such as cell division, motility, and intracellular transport. The interaction of these compounds with key tubulin residues, such as Thr 351 and Lys 350, suggests that they could interfere with microtubule dynamics, potentially disrupting cell division and inhibiting the proliferation of cancer cells. This finding highlights tubulin as a promising target for further investigation, offering valuable insight into the compounds' mechanisms of action and their potential as anticancer agents.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134677"},"PeriodicalIF":2.1,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143864364","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}
{"title":"Efficient one-pot four-component sequential synthesis of 5-acetyl-4-amino-3-(aryl)thieno[2,3-b]pyridin-6(7H)-ones in the presence of aluminum chloride","authors":"Hossein Mehrabi, Farzaneh Alizadeh-Bami, Zeynab Mohammadi","doi":"10.1016/j.tet.2025.134673","DOIUrl":"10.1016/j.tet.2025.134673","url":null,"abstract":"<div><div>A simple and efficient procedure for the synthesis of 5-acetyl-4-amino-3-(aryl)thieno[2,3-<em>b</em>]pyridin-6(7<em>H</em>)-ones by one-pot two-step reaction between 2-(1-arylethylidene)malononitriles, elemental sulfur, and Meldrum's acid in the presence of AlCl<sub>3</sub> (15 mol %) in 1,2-dichloroethane under refluxing conditions is reported.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134673"},"PeriodicalIF":2.1,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143856018","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}
{"title":"Visible-light-promoted oxidative decarboxylative acylation of acenaphthenone-2-ylidene ketones with α-keto carboxylic acids under metal, additonal oxidant and base-free condition","authors":"Tiyasa Dhar , Debasish Bera , Suvendu Maity , Chhanda Mukhopadhyay","doi":"10.1016/j.tet.2025.134674","DOIUrl":"10.1016/j.tet.2025.134674","url":null,"abstract":"<div><div>A metal and additional oxidant free, visible light induced decarboxylative acylation of acenaphthenone-2-ylidene ketone has been accomplished for the first time at room temperature utilizing ambient air as the only oxidant. By using 2,4,5,6-tetra(9H-carbazol-9- yl)isophthalonitrile (4CzIPN) as a photocatalyst under mild circumstance, this acylation has been carried out without the requirement of metal reagent, conventional heating and an additional base.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134674"},"PeriodicalIF":2.1,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143856019","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}
TetrahedronPub Date : 2025-04-18DOI: 10.1016/j.tet.2025.134668
Zhaobo Fu, Yanting Yu, Zeguo Fang, Qian Zhang, Dong Li
{"title":"Palladium-catalyzed aminocarbonylation of vinyl bromides with isocyanides for the synthesis of α,β-unsaturated amides","authors":"Zhaobo Fu, Yanting Yu, Zeguo Fang, Qian Zhang, Dong Li","doi":"10.1016/j.tet.2025.134668","DOIUrl":"10.1016/j.tet.2025.134668","url":null,"abstract":"<div><div>A palladium-catalyzed aminocarbonylation of vinyl bromides with isocyanides was developed, which provides the <em>α,β</em>-unsaturated amides in moderated to good yields. Both <em>α</em>- and <em>β</em>-bromoalkenes could be applied in this method and gave the corresponding linear or branched unsaturated amides with single configuration. It provided an efficient and facile method for the synthesis of <em>α,β</em>-unsaturated amides from readily available feedstocks.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134668"},"PeriodicalIF":2.1,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847887","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}
{"title":"Direct C–H selenylation of (Benz)imidazole and related heterocycles via cooperative action of palladium and silver catalyst","authors":"Pranali Prabhakar Thakur, Manali Pawar, Mahendra Patil","doi":"10.1016/j.tet.2025.134667","DOIUrl":"10.1016/j.tet.2025.134667","url":null,"abstract":"<div><div>The selenylation of (benz)imidazole and related heteroarenes has been successfully achieved using PdCl<sub>2</sub>/Ag<sub>2</sub>O/Xantphos as a catalytic system. This method exploits the cooperative action of palladium and silver catalyst to activate diaryl diselenides as well as C–H bonds of (benz)imidazole and related heteroarenes, enabling the effective coupling of selenium moieties with these heteroarenes. Control experiments involving variation in catalyst loading revealed the synergistic interaction between Pd and Ag catalyst in the reaction. The unification of these robust catalytic systems ensures optimal outcome in the synthesis of a diverse array of organoselenium compounds featuring aryl-heteroaryl scaffolds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"180 ","pages":"Article 134667"},"PeriodicalIF":2.1,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847888","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}