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Beilstein Journal of Organic Chemistry最新文献

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Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents. 省略醇共溶剂，优化了芳烃- s， n -烯酮缩醛的合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-20 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.97
Julius Krenzer, Thomas J J Müller
{"title":"Optimized synthesis of aroyl-<i>S,N</i>-ketene acetals by omission of solubilizing alcohol cosolvents.","authors":"Julius Krenzer, Thomas J J Müller","doi":"10.3762/bjoc.21.97","DOIUrl":"10.3762/bjoc.21.97","url":null,"abstract":"<p><p>Aroyl-<i>S</i>,<i>N</i>-ketene acetals are obtained by condensation of aroyl chlorides and 2-methyl-<i>N</i>-benzylbenzothiazolium salts in 1,4-dioxane at room temperature in short reaction time in 20-99% yield. This protocol represents a considerable improvement over the standard synthesis in 1,4-dioxane/ethanol mixtures at elevated temperatures.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1201-1206"},"PeriodicalIF":2.2,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12207251/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526322","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
Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers. 用于亚甲基交替共聚物的萘-熔融丙烷选择性单甲酰化反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-18 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.95
Kenichi Kato, Tatsuki Hiroi, Seina Okada, Shunsuke Ohtani, Tomoki Ogoshi
{"title":"Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers.","authors":"Kenichi Kato, Tatsuki Hiroi, Seina Okada, Shunsuke Ohtani, Tomoki Ogoshi","doi":"10.3762/bjoc.21.95","DOIUrl":"10.3762/bjoc.21.95","url":null,"abstract":"<p><p>Development of three-dimensional (3D) building blocks is a key to change tight molecular assemblies of rigid π-conjugated planes into organic functional materials endowed with molecular-size cavities. To increase the diversity of available 3D building blocks, we herein report electrophilic formylation of naphthalene-fused [3.3.3]- and [4.3.3]propellanes as the first selective single-point functionalization by virtue of through-space electronic communications between the naphthalene units. The propellane skeletons have well-defined 3D structures and moderate flexibility at the same time. Therefore, the monoformyl products are good precursors for soft materials which show molecular-size cavities and require desymmetrized building blocks. As a proof of concept, methylene-alternating copolymers were prepared by reduction to corresponding alcohols followed by acid-mediated condensation. The linear copolymers show good solubility and carbon dioxide adsorption.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1183-1191"},"PeriodicalIF":2.2,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12207256/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526327","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
Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C-H activation with directing groups. 增强化学合成计划：基于自动量子力学的定向基团C-H活化区域选择性预测。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-16 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.94
Julius Seumer, Nicolai Ree, Jan H Jensen
{"title":"Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C-H activation with directing groups.","authors":"Julius Seumer, Nicolai Ree, Jan H Jensen","doi":"10.3762/bjoc.21.94","DOIUrl":"10.3762/bjoc.21.94","url":null,"abstract":"<p><p>The mild and selective functionalization of carbon-hydrogen (C-H) bonds remains a pivotal challenge in organic synthesis, crucial for developing complex molecular architectures in pharmaceuticals, polymers, and agrochemicals. Despite advancements in directing group (DG) methodologies and computational approaches, predicting accurate regioselectivity in C-H activation poses significant difficulties due to the diversity and complexity of organic compounds. This study introduces a novel quantum mechanics-based computational workflow tailored for the regioselective prediction of C-H activation in the presence of DGs. Utilizing (semi-empirical) quantum calculations hierarchically, the workflow efficiently predicts outcomes by considering concerted metallation deprotonation mechanisms mediated by common catalysts like Pd(OAc)<sub>2</sub>. Our methodology not only identifies potential activation sites but also addresses the limitations of existing models by including a broader range of directing groups and reaction conditions while maintaining moderate computational cost. Validation against a comprehensive dataset reveals that the workflow achieves high accuracy, significantly surpassing traditional models in both speed and predictive capability. This development promises substantial advancements in the design of new synthetic routes, offering rapid and reliable regioselectivity predictions that are essential for accelerating innovation in materials science and medicinal chemistry.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1171-1182"},"PeriodicalIF":2.2,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12207270/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526320","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
Correction: Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates. 修正：通过姜黄素共轭加成到芳烯醚酸酯的高取代环己酮和四氢铬-4-酮的非对映选择性合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-16 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.93
Deepa Nair, Abhishek Tiwari, Banamali Laha, Lakshminarayana Satham, Irishi N N Namboothiri
{"title":"Correction: Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates.","authors":"Deepa Nair, Abhishek Tiwari, Banamali Laha, Lakshminarayana Satham, Irishi N N Namboothiri","doi":"10.3762/bjoc.21.93","DOIUrl":"10.3762/bjoc.21.93","url":null,"abstract":"<p><p>[This corrects the article DOI: 10.3762/bjoc.20.177.].</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1170"},"PeriodicalIF":2.2,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12207271/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526319","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
A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones. 咪唑吡啶融合异喹啉酮的多组分反应引发合成。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-13 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.92
Ashutosh Nath, John Mark Awad, Wei Zhang
{"title":"A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones.","authors":"Ashutosh Nath, John Mark Awad, Wei Zhang","doi":"10.3762/bjoc.21.92","DOIUrl":"10.3762/bjoc.21.92","url":null,"abstract":"<p><p>A new synthetic route initiated with Groebke-Blackburn-Bienaymé (GBB) followed by <i>N</i>-acylation, intramolecular Diels-Alder (IMDA), and dehydrative re-aromatization reactions for the synthesis of imidazopyridine-fused isoquinolinones is developed. Gaussian computation analysis on the effect of the substitution groups for the IMDA reaction is performed to understand the reaction mechanism.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1161-1169"},"PeriodicalIF":2.2,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12207252/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526318","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
Synthetic approach to borrelidin fragments: focus on key intermediates. borrelidin片段的合成方法：重点关注关键中间体。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-12 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.91
Yudhi Dwi Kurniawan, Zetryana Puteri Tachrim, Teni Ernawati, Faris Hermawan, Ima Nurasiyah, Muhammad Alfin Sulmantara
{"title":"Synthetic approach to borrelidin fragments: focus on key intermediates.","authors":"Yudhi Dwi Kurniawan, Zetryana Puteri Tachrim, Teni Ernawati, Faris Hermawan, Ima Nurasiyah, Muhammad Alfin Sulmantara","doi":"10.3762/bjoc.21.91","DOIUrl":"10.3762/bjoc.21.91","url":null,"abstract":"<p><p>Borrelidin, a naturally occurring antibiotic, has attracted considerable interest due to its diverse biological activities and complex molecular architecture. Although extensive research has explored its pharmacological properties and various synthetic approaches, significant challenges remain in the efficient synthesis of borrelidin and its analogs. Existing literature largely focuses on total synthesis, bioactivity, and structural modifications, leaving a notable gap in fragment-focused synthesis, particularly for its intricate substructures. This review seeks to address this gap by offering a detailed examination of borrelidin fragment synthesis, highlighting key challenges and innovative strategies involved. By pinpointing unresolved synthetic hurdles, this work advocates for a fragment-focused approach as a crucial step toward advancing borrelidin research and expanding its potential applications.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1135-1160"},"PeriodicalIF":2.2,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12207266/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526329","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
Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold. 抗疟药物1,2,4-三唑[4,3-a]吡嗪支架的胺化反应研究。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-10 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.90
Henry S T Smith, Ben Giuliani, Kanchana Wijesekera, Kah Yean Lum, Sandra Duffy, Aaron Lock, Jonathan M White, Vicky M Avery, Rohan A Davis
{"title":"Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-<i>a</i>]pyrazine scaffold.","authors":"Henry S T Smith, Ben Giuliani, Kanchana Wijesekera, Kah Yean Lum, Sandra Duffy, Aaron Lock, Jonathan M White, Vicky M Avery, Rohan A Davis","doi":"10.3762/bjoc.21.90","DOIUrl":"10.3762/bjoc.21.90","url":null,"abstract":"<p><p>1,2,4-Triazolo[4,3-<i>a</i>]pyrazines have previously been explored by the Open Source Malaria project as potent in vitro and in vivo antimalarial drug leads. With a view to generating a library of unique antimalarial 1,2,4-triazolo[4,3-<i>a</i>]pyrazines and exploring regiochemical preference for nucleophilic amines, we utilised the known synthetic 5-chloro-3-(4-chlorophenyl)-[1,2,4]triazolo[4,3-<i>a</i>]pyrazine (<b>1</b>) as a scaffold for aminations with 14 commercially available primary amines. Reacting scaffold <b>1</b> with excess primary amine at room temperature for 16 h generated the desired amine analogues in respectable yields (18-87%) and high purity (≥95%) following chromatography workup. The structures of the 14 previously undescribed amine analogues <b>2</b>-<b>15</b> were fully characterised following 1D/2D NMR, UV, and HRMS data analyses. X-ray crystallographic analysis of crystals obtained from the aminated products <b>2</b>, <b>7</b>, <b>10</b>, and <b>15</b> are also reported here. The new library of amine-substituted triazolopyrazines was screened against the <i>Plasmodium falciparum</i> 3D7 strain. The tertiary alkylamine products <b>10</b>-<b>14</b> displayed antimalarial activity with IC<sub>50</sub> values ranging from 9.90 to 23.30 µM against <i>P. falciparum</i> 3D7, with compounds <b>10</b>-<b>12</b> demonstrating no toxicity at 80 µM against the human embryonic kidney cell line HEK293.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1126-1134"},"PeriodicalIF":2.2,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12207250/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144526321","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
Gold extraction at the molecular level using α- and β-cyclodextrins. α-和β-环糊精在分子水平上提取金。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-06 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.89
Susana Santos Braga
{"title":"Gold extraction at the molecular level using α- and β-cyclodextrins.","authors":"Susana Santos Braga","doi":"10.3762/bjoc.21.89","DOIUrl":"10.3762/bjoc.21.89","url":null,"abstract":"<p><p>Cyclodextrins (CDs) are known for their ability to form supramolecular interactions with a wide range of guest molecules. In this review, focus is given on the inclusion of complex aurate ions such as tetrabromoaurate, dicyanoaurate and a few other tetrahaloaurates. The review describes the properties of self-assembly of cyclodextrins with these ions, with highlight to α-CD and, more recently, β-CD, requiring the use of a co-former/precipitating agent. Practical applications of this ability are directed to the selective isolation of gold from a variety of sources, spanning from gold-rich mining ores and tailings/mining wastes to gold-bearing metal scraps obtained from disposed electronic devices. Moreover, it describes the development of a method based on spontaneous complex formation between α-CD and tetrabromoaurate and its current status of use in a few mining sites in the United States.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1116-1125"},"PeriodicalIF":2.2,"publicationDate":"2025-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12152312/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144274131","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
A versatile route towards 6-arylpipecolic acids. 合成6-芳基果酸的通用途径。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-06-04 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.88
Erich Gebel, Cornelia Göcke, Carolin Gruner, Norbert Sewald
{"title":"A versatile route towards 6-arylpipecolic acids.","authors":"Erich Gebel, Cornelia Göcke, Carolin Gruner, Norbert Sewald","doi":"10.3762/bjoc.21.88","DOIUrl":"10.3762/bjoc.21.88","url":null,"abstract":"<p><p>Pipecolic acid is known as a non-proteinogenic amino acid with a secondary amine. It contains a six-membered ring and is, like its five-membered correlate, known for its secondary structure inducing properties, which are particularly useful in the design of peptide conformations. We present a new and improved way to generate enantiomerically pure pipecolic acid derivatives with aryl modifications in C<sup>6</sup> position by utilising the chiral pool of a non-proteinogenic amino acid in combination with transition metal-catalysed cross-coupling reactions. Moreover, we present an in-depth NMR analysis of the key intermediate steps, which illustrates the conformational constraints in accordance with coupling constants and resulting dihedral angles.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1104-1115"},"PeriodicalIF":2.2,"publicationDate":"2025-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12152316/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144274130","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
Supramolecular assembly of hypervalent iodine macrocycles and alkali metals. 高价碘大环与碱金属的超分子组装。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-05-30 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.87
Krishna Pandey, Lucas X Orton, Grayson Venus, Waseem A Hussain, Toby Woods, Lichang Wang, Kyle N Plunkett
{"title":"Supramolecular assembly of hypervalent iodine macrocycles and alkali metals.","authors":"Krishna Pandey, Lucas X Orton, Grayson Venus, Waseem A Hussain, Toby Woods, Lichang Wang, Kyle N Plunkett","doi":"10.3762/bjoc.21.87","DOIUrl":"10.3762/bjoc.21.87","url":null,"abstract":"<p><p>This study explores the solution- and solid-state assembly of phenylalanine-based hypervalent iodine macrocycles (HIMs) with lithium and sodium cations. The metal cation binding of HIMs was evaluated by addition of lithium tetrakis(pentafluorophenyl)borate ethyl etherate LiBArF<sub>20</sub> and sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate NaBArF<sub>24</sub>. The electron-rich, outwardly projected carbonyl oxygens of the HIM co-crystalize with the cations into bent supramolecular architectures. Both crystal structures show a pattern of assembly between HIM and metal cation in 2:1 ratio. While association with sodium leads to a polymer-like network, the lithium crystal structure was limited to dimeric assemblies of HIM. In the lithium-coordinating complex, the oxygen-lithium-oxygen bond angle is approximately 98.83°, displaying a closer arrangement of two HIMs. In contrast, the sodium complex exhibits a more open orientation of two HIMs with an oxygen-sodium-oxygen bond angle close to 167.98°. Lastly, a comparative study of association constants and binding energies for phenylalanine-based HIM with LiBArF<sub>20</sub> and NaBArF<sub>24</sub> are presented.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1095-1103"},"PeriodicalIF":2.2,"publicationDate":"2025-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12130623/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144214791","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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