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Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation 通过三组份苯并吡喃法异氰酸酯引导合成间位苯乙烯类化合物
IF 2.7 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-02 DOI: 10.3762/bjoc.20.188
Andrey R. Galeev, Maksim V. Dmitriev, Alexander S. Novikov, Andrey N. Maslivets
{"title":"Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation","authors":"Andrey R. Galeev, Maksim V. Dmitriev, Alexander S. Novikov, Andrey N. Maslivets","doi":"10.3762/bjoc.20.188","DOIUrl":"https://doi.org/10.3762/bjoc.20.188","url":null,"abstract":"<p><font size='+1'><b>Abstract</b></font></p>\u0000<p>A one-pot three-component synthesis of substituted <i>meta</i>-hetarylanilines from heterocycle-substituted 1,3-diketones has been developed. The electron-withdrawing power of the heterocyclic substituent (which can be estimated on the basis of calculated Hammett constants) in the 1,3-diketone plays a pivotal role in the studied reaction. The series of <i>meta</i>-hetarylanilines prepared (21&#8211;85% isolated yield) demonstrates the synthetic utility of the developed method.</p>\u0000<p align='center'><img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-188-graphical-abstract.png?max-width=550' border='0'/></p>\u0000<p><i>Beilstein J. Org. Chem.</i> <b>2024,</b> <i>20,</i> 2208&#8211;2216.&#160;doi:10.3762/bjoc.20.188</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142185004","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
Electrochemical allylations in a deep eutectic solvent 深共晶溶剂中的电化学烯丙基化反应
IF 2.7 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-09-02 DOI: 10.3762/bjoc.20.189
Sophia Taylor, Scott T. Handy
{"title":"Electrochemical allylations in a deep eutectic solvent","authors":"Sophia Taylor, Scott T. Handy","doi":"10.3762/bjoc.20.189","DOIUrl":"https://doi.org/10.3762/bjoc.20.189","url":null,"abstract":"<p><font size='+1'><b>Abstract</b></font></p>\u0000<p>Electrosynthesis is a technique that is attracting increased attention and has many appealing features, particularly its potential greenness. At the same time, electrosynthesis requires a solvent and a supporting electrolyte in order for current to pass through the reaction. These are effectively consumable reagents unless a convenient means of recycling can be developed. As part of our interest in unusual solvents and electrochemistry, we explored the application of simple, inexpensive, and recyclable deep eutectic solvents to the allylation of carbonyls. While several sets of conditions were developed, the goal of avoiding stoichiometric amounts of metal has proven elusive. Still, a deep eutectic solvent can be used to plate out and thus recover the metal used, offering an interesting new option for electrochemical allylations.</p>\u0000<p align='center'><img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-189-graphical-abstract.png?max-width=550' border='0'/></p>\u0000<p><i>Beilstein J. Org. Chem.</i> <b>2024,</b> <i>20,</i> 2217&#8211;2224.&#160;doi:10.3762/bjoc.20.189</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142185005","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
Natural resorcylic lactones derived from alternariol. 从交让木酚中提取的天然树脂内酯。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-30 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.187
Joachim Podlech
{"title":"Natural resorcylic lactones derived from alternariol.","authors":"Joachim Podlech","doi":"10.3762/bjoc.20.187","DOIUrl":"10.3762/bjoc.20.187","url":null,"abstract":"<p><p>In this overview, naturally occurring resorcylic lactones biosynthetically derived from alternariol and almost exclusively produced by fungi, are discussed with view on their isolation, structure, biological activities, biosynthesis, and total syntheses. This class of compounds consists until now of 127 naturally occurring compounds, with very divers structural motifs. Although only a handful of these toxins (i.e., alternariol and its 9-<i>O</i>-methyl ether, altenusin, dehydroaltenusin, altertenuol, and altenuene) were frequently found and isolated as fungal contaminants in food and feed and have been investigated in significant detail, further metabolites, which were much more rarely found as natural products, similarly show interesting biological activities.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2171-2207"},"PeriodicalIF":2.2,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11368053/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118900","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
Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties. 新型三萜基二吡咯烷酮（DPMs）：合成、光谱表征和光物理性质。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-29 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.186
Shakeel Alvi, Rashid Ali
{"title":"Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties.","authors":"Shakeel Alvi, Rashid Ali","doi":"10.3762/bjoc.20.186","DOIUrl":"10.3762/bjoc.20.186","url":null,"abstract":"<p><p>For the first time, herein, we report the synthetic part of the truxene-centred mono-, di- and tri-substituted dipyromethanes (DPMs) in good yields (60-80%) along with their preliminary photophysical (absorption, emission and time resolved fluorescence lifetime) properties. The condensation reaction for assembling the required DPMs were catalyzed with trifluoroacetic acid (TFA) at 0 °C to room temperature (rt), and the stable dipyrromethanes were purified through silica-gel column chromatography. After successfully synthesizing these easy-to-make yet interesting molecules, they were fully characterized by means of the standard spectroscopic techniques (<sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS). We are of the opinion that these truxene-based systems will be useful for diverse applications in future studies.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2163-2170"},"PeriodicalIF":2.2,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11368050/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118901","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
Finding the most potent compounds using active learning on molecular pairs. 利用分子对的主动学习寻找最有效的化合物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-27 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.185
Zachary Fralish, Daniel Reker
{"title":"Finding the most potent compounds using active learning on molecular pairs.","authors":"Zachary Fralish, Daniel Reker","doi":"10.3762/bjoc.20.185","DOIUrl":"10.3762/bjoc.20.185","url":null,"abstract":"<p><p>Active learning allows algorithms to steer iterative experimentation to accelerate and de-risk molecular optimizations, but actively trained models might still exhibit poor performance during early project stages where the training data is limited and model exploitation might lead to analog identification with limited scaffold diversity. Here, we present ActiveDelta, an adaptive approach that leverages paired molecular representations to predict improvements from the current best training compound to prioritize further data acquisition. We apply the ActiveDelta concept to both graph-based deep (Chemprop) and tree-based (XGBoost) models during exploitative active learning for 99 K<sub>i</sub> benchmarking datasets. We show that both ActiveDelta implementations excel at identifying more potent inhibitors compared to the standard exploitative active learning implementations of Chemprop, XGBoost, and Random Forest. The ActiveDelta approach is also able to identify more chemically diverse inhibitors in terms of their Murcko scaffolds. Finally, deep models such as Chemprop trained on data selected through ActiveDelta approaches can more accurately identify inhibitors in test data created through simulated time-splits. Overall, this study highlights the large potential for molecular pairing approaches to further improve popular active learning strategies in low data regimes by enabling faster and more accurate identification of more diverse molecular hits against critical drug targets.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2152-2162"},"PeriodicalIF":2.2,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11368049/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118899","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
O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization. 基于环状 β-酮砜的含 O、S、Se 的 Biginelli 产物及其后官能化。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-27 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.184
Kateryna V Dil, Vitalii A Palchykov
{"title":"O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization.","authors":"Kateryna V Dil, Vitalii A Palchykov","doi":"10.3762/bjoc.20.184","DOIUrl":"10.3762/bjoc.20.184","url":null,"abstract":"<p><p>A one-pot three-component Biginelli synthesis of dihydropyrimidinones/thiones/selenones via acetic acid or solvent-free Yb(OTf)<sub>3</sub>-catalyzed tandem reaction of β-ketosulfone (dihydro-2<i>H</i>-thiopyran-3(4<i>H</i>)-one-1,1-dioxide), an appropriate urea, and arylaldehyde has been developed. The reaction proceeds with high chemo- and regioselectivity to give diverse DHPMs in reasonable yields up to 95%. Moreover, an SO<sub>2</sub>-containing analogue of anticancer drug-candidate enastron (SO<sub>2</sub> vs C=O) was obtained by using the here reported method in gram scale. We also demonstrate the reactivity of the Biginelli product in various directions - synthesis of condensed thiazoles and tetrazoles. In silico assessment of ADMET parameters shows that most compounds meet the lead-likeness requirements. The biological profiles of new compounds demonstrate high probability levels of activity against the following pathogens/diseases: <i>Candida albicans, Alphis gossypii, Tripomastigote Chagas, Tcruzi amastigota, Tcruzi epimastigota, Leishmania amazonensis,</i> and <i>Dengue larvicida.</i></p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2143-2151"},"PeriodicalIF":2.2,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11368051/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118902","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
Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis. 异氰酸酯与杂原子自由基的自由基反应在有机合成中的功效。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-26 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.182
Akiya Ogawa, Yuki Yamamoto
{"title":"Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis.","authors":"Akiya Ogawa, Yuki Yamamoto","doi":"10.3762/bjoc.20.182","DOIUrl":"10.3762/bjoc.20.182","url":null,"abstract":"<p><p>Isocyanide is a promising synthetic reagent not only as a one-carbon homologation reagent but also as a nitrogen source for nitrogen-containing molecules. Because of their isoelectronic structure with carbon monoxide, isocyanides also react with nucleophiles, electrophiles, carbon radicals, and transition metal reagents, and are widely used in organic synthesis. On the other hand, the use of isocyanides in reactions with heteroatom radicals is limited. However, the reaction of isocyanides with heteroatom radicals is a promising synthetic tool for the construction of nitrogen-containing organic molecules modified with a variety of heteroatoms. In this Perspective, we review the addition and cyclization reactions of heteroatom radicals with isocyanides and discuss the synthetic prospects of the reaction of isocyanides with heteroatom radicals.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2114-2128"},"PeriodicalIF":2.2,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11368054/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118897","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
Factors influencing the performance of organocatalysts immobilised on solid supports: A review. 影响固定在固体支持物上的有机催化剂性能的因素：综述。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-26 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.183
Zsuzsanna Fehér, Dóra Richter, Gyula Dargó, József Kupai
{"title":"Factors influencing the performance of organocatalysts immobilised on solid supports: A review.","authors":"Zsuzsanna Fehér, Dóra Richter, Gyula Dargó, József Kupai","doi":"10.3762/bjoc.20.183","DOIUrl":"10.3762/bjoc.20.183","url":null,"abstract":"<p><p>Organocatalysis has become a powerful tool in synthetic chemistry, providing a cost-effective alternative to traditional catalytic methods. The immobilisation of organocatalysts offers the potential to increase catalyst reusability and efficiency in organic reactions. This article reviews the key parameters that influence the effectiveness of immobilised organocatalysts, including the type of support, immobilisation techniques and the resulting interactions. In addition, the influence of these factors on catalytic activity, selectivity and recyclability is discussed, providing an insight into optimising the performance of immobilised organocatalysts for practical applications in organic chemistry.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2129-2142"},"PeriodicalIF":2.2,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11368055/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142118898","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
From perfluoroalkyl aryl sulfoxides to ortho thioethers. 从全氟烷基芳基硫醚到正硫醚。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-23 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.181
Yang Li, Guillaume Dagousset, Emmanuel Magnier, Bruce Pégot
{"title":"From perfluoroalkyl aryl sulfoxides to <i>ortho</i> thioethers.","authors":"Yang Li, Guillaume Dagousset, Emmanuel Magnier, Bruce Pégot","doi":"10.3762/bjoc.20.181","DOIUrl":"10.3762/bjoc.20.181","url":null,"abstract":"<p><p>Access to original <i>ortho</i> thioether derivatives was achieved through a [3,3]-rearrangement in a one-pot two-step protocol. Several aryl-SCF<sub>3</sub> compounds are reported by variation of the nitrile or of the trifluoroalkyl sulfoxide starting material. The variation of the perfluoroalkyl chain was also possible.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2108-2113"},"PeriodicalIF":2.2,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11346307/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142071856","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
Cage-like microstructures via sequential Ugi reactions in aqueous emulsions. 在水性乳液中通过连续的乌基反应形成笼状微结构。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-08-22 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.179
Rita S Alqubelat, Yaroslava A Menzorova, Maxim A Mironov
{"title":"Cage-like microstructures via sequential Ugi reactions in aqueous emulsions.","authors":"Rita S Alqubelat, Yaroslava A Menzorova, Maxim A Mironov","doi":"10.3762/bjoc.20.179","DOIUrl":"10.3762/bjoc.20.179","url":null,"abstract":"<p><p>Cage-like microstructures were obtained in two steps by sequential Ugi reactions. At the first stage, submicron colloidal particles based on carboxymethylcellulose and chitosan with a domain structure were obtained in an aqueous suspension. In the second stage, the Ugi reaction was carried out on the surface of the Pickering emulsions with toluene. Removal of toluene and redissolution in water resulted in colloidosomes with large holes on the surface. Varying the cross-link density during the Ugi reaction made it possible to obtain structures with different hole sizes.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2078-2083"},"PeriodicalIF":2.2,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11346303/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142071854","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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