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3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units. 3,3'-联BINOL大环：具有一个或两个BINOL单元的冠醚的优化合成。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-28 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.134
Somayyeh Kheirjou, Jan Riebe, Maike Thiele, Christoph Wölper, Jochen Niemeyer
{"title":"3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units.","authors":"Somayyeh Kheirjou, Jan Riebe, Maike Thiele, Christoph Wölper, Jochen Niemeyer","doi":"10.3762/bjoc.21.134","DOIUrl":"10.3762/bjoc.21.134","url":null,"abstract":"<p><p>Chiral macrocycles hold significant importance in various scientific fields due to their unique structural and chemical properties. By controlling their size, shape, and substituents, chiral macrocycles offer a platform for designing and synthesizing highly efficient catalysts, chemosensors, and functional materials. We have recently made strides in developing macrocyclic organocatalysts; however, their synthesis remains challenging. In this work, we aimed to discover a straightforward method for producing a diverse range of chiral macrocycles, thereby enabling further exploration in the field of interlocked and macrocyclic organocatalysts. We successfully established optimized synthetic routes for the synthesis of chiral macrocycles containing one or two stereogenic units, featuring varying ring sizes and substituents (21 examples in total).</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1719-1729"},"PeriodicalIF":2.1,"publicationDate":"2025-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415923/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028896","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
Convenient alternative synthesis of the Malassezia-derived virulence factor malassezione and related compounds. 马拉色菌衍生毒力因子马拉色酮及其相关化合物的方便替代合成。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-28 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.135
Karu Ramesh, Stephen L Bearne
{"title":"Convenient alternative synthesis of the <i>Malassezia</i>-derived virulence factor malassezione and related compounds.","authors":"Karu Ramesh, Stephen L Bearne","doi":"10.3762/bjoc.21.135","DOIUrl":"10.3762/bjoc.21.135","url":null,"abstract":"<p><p>Lipophilic yeasts of the genus <i>Malassezia</i> are commensal fungi that constitute the normal skin microbiota but may become pathogenic. These fungi, especially <i>M. furfur</i>, convert tryptophan into various alkaloid indoles such as malassezione, which may serve as virulence factors. To facilitate testing of malassezione as an aryl hydrocarbon receptor agonist and potential glucokinase activator, we developed a convenient synthetic route from commercially available indole-3-acetic acid. Treatment of the <i>N</i>-Boc-protected indole-3-acetic acid with <i>N</i>-ethyl-<i>N</i>'-(3-dimethylaminopropyl)carbodiimide (EDC) in the presence of DMAP generates the <i>N</i>,<i>N</i>'-Boc-protected malassezione, which upon deprotection yields malassezione in an overall yield of ca. 20%. This is an improvement over the preparation of the isonitrile followed by an Fe hydride initiated isonitrile-olefin intramolecular coupling reaction, which generated malassezione with an overall yield of ca. 5%. Furthermore, the present method may also be used to prepare related compounds.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1730-1736"},"PeriodicalIF":2.1,"publicationDate":"2025-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415918/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028842","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
Approaches to stereoselective 1,1'-glycosylation. 立体选择性1,1'-糖基化的方法。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-27 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.133
Daniele Zucchetta, Alla Zamyatina
{"title":"Approaches to stereoselective 1,1'-glycosylation.","authors":"Daniele Zucchetta, Alla Zamyatina","doi":"10.3762/bjoc.21.133","DOIUrl":"10.3762/bjoc.21.133","url":null,"abstract":"<p><p>Nonreducing disaccharides are prevalent in non-mammalian glycans and glycolipids, serving as pivotal structural components in mycobacterial glycans, microbial oligosaccharide and nucleoside antibiotics, as well as biologically active mimetics of bacterial pathogen-associated molecular patterns (PAMPs). As integral components of PAMPs, 1,1'-linked disaccharide-containing biomolecules play important roles in host-pathogen interactions, cellular signaling, and pathogenesis. Accessing complex biomolecules containing nonreducing disaccharides is often hindered by difficulties in isolating them from natural sources, which can result in impure or degraded products, particularly when sensitive functional groups are involved. Consequently, approaches to 1,1'-glycosylation for the synthesis of nonreducing disaccharides with defined anomeric configurations are essential for the development of 1,1'-disaccharide-containing biomolecules used in vaccine research, as well as for therapeutic and diagnostic applications. The assembly of nonreducing 1,1'-linked disaccharides presents greater challenges than conventional chemical glycosylation due to the need for simultaneous control of stereochemistry at two anomeric centers. The structural complexity of natural biomolecules entailing 1,1'-disaccharides, which feature asymmetrically distributed functional groups across their two pyranose rings, emphasizes the importance of robust, stereoselective synthetic strategies capable of producing fully orthogonally protected 1,1'-linked sugars suitable for selective chemical modification. This review highlights recent advances in 1,1'-glycosylation and provides an overview of selected glycosylation strategies, including those aimed at forming α,β-, β,β-, and α,α-1,1'-glycosidic linkages. Particular emphasis is placed on the challenges of achieving stereoselectivity with lactol glycosyl acceptors, which commonly exist as mixtures of anomers and are therefore problematic to use in chemical glycosylation reactions.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1700-1718"},"PeriodicalIF":2.1,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415924/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028835","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
Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade. 连续流强化硝化过程：回顾过去十年的技术发展和实际应用。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-26 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.132
Feng Zhou, Chuansong Duanmu, Yanxing Li, Jin Li, Haiqing Xu, Pan Wang, Kai Zhu
{"title":"Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade.","authors":"Feng Zhou, Chuansong Duanmu, Yanxing Li, Jin Li, Haiqing Xu, Pan Wang, Kai Zhu","doi":"10.3762/bjoc.21.132","DOIUrl":"10.3762/bjoc.21.132","url":null,"abstract":"<p><p>Flow chemistry technology has demonstrated significant potential in advancing the green transformation of the chemical industry while enhancing inherent process safety. Safety, cost-effectiveness, and operational efficiency serve as pivotal drivers for advancing flow chemistry in nitration processes. This review provides a comprehensive analysis of the continuous-flow nitration technology - a process historically recognized as one of the most hazardous industrial operations - focusing on its technological advancements in process design, reaction kinetics characterization, and practical implementation over the past decade. Detailed discussions encompass system configuration strategies, critical process parameters and operating ranges, performance evaluation metrics, universal methodologies for kinetics analysis, safety assessment protocols, and scale-up approaches. The presented content aims to offer actionable guidance for researchers and engineers engaged in the development of continuous-flow nitration systems.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1678-1699"},"PeriodicalIF":2.1,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415922/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028816","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
Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides. 立体选择性半乳糖丙酮酰化合成细菌荚膜多糖的结构分析。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-21 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.131
Tsun-Yi Chiang, Mei-Huei Lin, Chun-Wei Chang, Jinq-Chyi Lee, Cheng-Chung Wang
{"title":"Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides.","authors":"Tsun-Yi Chiang, Mei-Huei Lin, Chun-Wei Chang, Jinq-Chyi Lee, Cheng-Chung Wang","doi":"10.3762/bjoc.21.131","DOIUrl":"10.3762/bjoc.21.131","url":null,"abstract":"<p><p>Pyruvate ketal is a biologically essential moiety due to its key role as an intermediate in metabolic pathways, serving as a key precursor for the synthesis of various essential biomolecules in organisms. However, the <i>R</i>/<i>S</i> stereochemistry of pyruvate ketal is difficult to control through chemical methods. In this study, the acid-labile pyruvate ketal linked to the 4- and 6-positions of galactose was cautiously constructed, and the X-ray analysis of the <i>R</i>-configured product was successfully obtained. Subsequently, the compound was used for the synthesis of zwitterionic polysaccharide A1 (PS A1) precursor, and a clear structural elucidation was applied by using nuclear magnetic resonance and X-ray.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1671-1677"},"PeriodicalIF":2.1,"publicationDate":"2025-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415908/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028893","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
Influence of the cation in hypophosphite-mediated catalyst-free reductive amination. 次磷酸盐介导的无催化剂还原胺化反应中阳离子的影响。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-20 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.130
Natalia Lebedeva, Fedor Kliuev, Olesya Zvereva, Klim Biriukov, Evgeniya Podyacheva, Maria Godovikova, Oleg I Afanasyev, Denis Chusov
{"title":"Influence of the cation in hypophosphite-mediated catalyst-free reductive amination.","authors":"Natalia Lebedeva, Fedor Kliuev, Olesya Zvereva, Klim Biriukov, Evgeniya Podyacheva, Maria Godovikova, Oleg I Afanasyev, Denis Chusov","doi":"10.3762/bjoc.21.130","DOIUrl":"10.3762/bjoc.21.130","url":null,"abstract":"<p><p>Reducing agents with phosphorus-hydrogen bond, such as sodium hypophosphite, phosphite, and hypophosphorous acid are commercially available in bulk amounts, however, their usage is understudied in organic processes. While NaH<sub>2</sub>PO<sub>2</sub> has proved to be an efficient four-electron reductant in the catalyst-free reductive amination, the influence of cation in hypophosphite salt has not been studied yet. This issue is a fundamentally important factor. In the present work, the reactivity of the hypophosphites of alkali metals (Li, K, Rb, and Cs) in reductive amination was explored for the first time. A set of secondary and tertiary amines was synthesized from various types of carbonyl compounds and amines. The remedy for Parkinson's disease, piribedil, was obtained in high yield. The plausible mechanism of the elaborated process was proposed and supported by DFT calculations.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1661-1670"},"PeriodicalIF":2.1,"publicationDate":"2025-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415911/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028864","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
Catalytic asymmetric reactions of isocyanides for constructing non-central chirality. 异氰酸酯非中心手性的催化不对称反应。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-19 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.129
Jia-Yu Liao
{"title":"Catalytic asymmetric reactions of isocyanides for constructing non-central chirality.","authors":"Jia-Yu Liao","doi":"10.3762/bjoc.21.129","DOIUrl":"10.3762/bjoc.21.129","url":null,"abstract":"<p><p>Beyond the conventional carbon-centered chirality, catalytic asymmetric transformations of isocyanides have recently emerged as a powerful strategy for the efficient synthesis of structurally diverse scaffolds featuring axial, planar, helical, and inherent chirality. Herein, we summarize the exciting achievements in this rapidly evolving field. These elegant examples have been organized and presented based on the reaction type as well as the resulting chirality form. Additionally, we provide a perspective on the current limitations and future opportunities, aiming to inspire further advances in this area.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1648-1660"},"PeriodicalIF":2.1,"publicationDate":"2025-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415902/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028811","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
Photocatalysis and photochemistry in organic synthesis. 有机合成中的光催化和光化学。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-18 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.128
Timothy Noël, Bartholomäus Pieber
{"title":"Photocatalysis and photochemistry in organic synthesis.","authors":"Timothy Noël, Bartholomäus Pieber","doi":"10.3762/bjoc.21.128","DOIUrl":"10.3762/bjoc.21.128","url":null,"abstract":"","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1645-1647"},"PeriodicalIF":2.1,"publicationDate":"2025-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415921/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145028887","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
Formal synthesis of a selective estrogen receptor modulator with tetrahydrofluorenone structure using [3 + 2 + 1] cycloaddition of yne-vinylcyclopropanes and CO. 炔-乙烯基环丙烷和一氧化碳[3 + 2 + 1]环加成合成四氢芴酮结构选择性雌激素受体调节剂。
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-14 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.127
Jing Zhang, Guanyu Zhang, Hongxi Bai, Zhi-Xiang Yu
{"title":"Formal synthesis of a selective estrogen receptor modulator with tetrahydrofluorenone structure using [3 + 2 + 1] cycloaddition of yne-vinylcyclopropanes and CO.","authors":"Jing Zhang, Guanyu Zhang, Hongxi Bai, Zhi-Xiang Yu","doi":"10.3762/bjoc.21.127","DOIUrl":"10.3762/bjoc.21.127","url":null,"abstract":"<p><p>A formal synthesis of product <b>VI</b> with tetrahydroflurenone structure as selective estrogen receptor modulator has been realized. The Rh-catalyzed [3 + 2 + 1] reaction of yne-vinylcyclopropanes and CO (20 mmol scale, in 87% yield) for building the 6/5/5 skeleton, and a Heck coupling reaction constructing the [3.2.1] framework, are the two key reactions in this 11-step synthesis.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1639-1644"},"PeriodicalIF":2.1,"publicationDate":"2025-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12362305/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144940682","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
On the aromaticity and photophysics of 1-arylbenzo[a]imidazo[5,1,2-cd]indolizines as bicolor fluorescent molecules for barium tagging in the study of double-beta decay of 136Xe. 136Xe双衰变研究中1-芳基苯并[a]咪唑[5,1,2-cd]吲哚啉作为钡标记的双色荧光分子的芳性和光物理性质
IF 2.1 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2025-08-13 eCollection Date: 2025-01-01 DOI: 10.3762/bjoc.21.126
Eric Iván Velazco-Cabral, Fernando Auria-Luna, Juan Molina-Canteras, Miguel A Vázquez, Iván Rivilla, Fernando P Cossío
{"title":"On the aromaticity and photophysics of 1-arylbenzo[<i>a</i>]imidazo[5,1,2-<i>cd</i>]indolizines as bicolor fluorescent molecules for barium tagging in the study of double-beta decay of <sup>136</sup>Xe.","authors":"Eric Iván Velazco-Cabral, Fernando Auria-Luna, Juan Molina-Canteras, Miguel A Vázquez, Iván Rivilla, Fernando P Cossío","doi":"10.3762/bjoc.21.126","DOIUrl":"10.3762/bjoc.21.126","url":null,"abstract":"<p><p>In this paper, the behavior of a bicolor fluorescent indicator for the detection of barium cations formed by double-beta decay of <sup>136</sup>Xe is analyzed by means of computational tools. Both DFT and TDDFT permit to understand the origin of the bicolor fluorescent signal emitted by 1-arylbenzo[<i>a</i>]imidazo[5,1,2-<i>cd</i>]indolizines in the free and Ba<sup>2+</sup>-bound states. The aromatic character of the fluorophore is analyzed by means of energetic (hyperhomodesmotic equations), structural (harmonic oscillator model of aromaticity, HOMA) and magnetic (nucleus independent chemical shifts, NICS) criteria. It is concluded that the aromatic character of the fluorophore is better described as the combination of two aromatic subunits integrated in the polycyclic system. Different DFT functional are used to analyze the photochemical behavior of this family of sensors. It is concluded that PBE0 and M06 functionals describe better the excitation process in the free state, whereas interaction of the sensor with Ba<sup>2+</sup> requires the M06L functional. TDDFT analysis of the emission spectra shows larger errors, which have been corrected by means of a structural model. The bicolor behavior is rationalized based on the decoupling between the <i>para</i>-phenylene and benzo[<i>a</i>]imidazo[5,1,2-<i>cd</i>]indolizine components that results in a blue shift upon Ba<sup>2+</sup> coordination.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"1627-1638"},"PeriodicalIF":2.1,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12362309/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144940754","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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