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Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates. 合成三羰基化丙炔胺并将其转化为 2,5-二取代的噁唑-4-羧酸盐。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-06 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.238
Kento Iwai, Akari Hikasa, Kotaro Yoshioka, Shinki Tani, Kazuto Umezu, Nagatoshi Nishiwaki
{"title":"Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates.","authors":"Kento Iwai, Akari Hikasa, Kotaro Yoshioka, Shinki Tani, Kazuto Umezu, Nagatoshi Nishiwaki","doi":"10.3762/bjoc.20.238","DOIUrl":"https://doi.org/10.3762/bjoc.20.238","url":null,"abstract":"<p><p>The <i>N</i>,<i>O</i>-acetal derived from diethyl mesoxalate (DEMO) undergoes elimination of acetic acid upon treatment with a base, leading to the formation of <i>N</i>-acylimine in situ. Lithium acetylide readily attacks the imino group to afford <i>N</i>,1,1-tricarbonylated propargylamines. When the resulting propargylamine reacts with butyllithium, ring closure occurs between the ethynyl and carbamoyl groups, yielding 2,5-disubstituted oxazole-4-carboxylates. This cyclization also occurs when the propargylamine is heated with ammonium acetate, resulting in double activation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2827-2833"},"PeriodicalIF":2.2,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552412/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614082","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
Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide. 用于检测硫化氢水溶液的双金属铽（III）/铜（II）化学传感器的研究。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-05 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.237
Parvathy Mini, Michael R Grace, Genevieve H Dennison, Kellie L Tuck
{"title":"Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide.","authors":"Parvathy Mini, Michael R Grace, Genevieve H Dennison, Kellie L Tuck","doi":"10.3762/bjoc.20.237","DOIUrl":"https://doi.org/10.3762/bjoc.20.237","url":null,"abstract":"<p><p>The chemosensor properties of a bimetallic terbium(III)/copper(II) complex functionalized with a 4-(2-pyridyl)-1,2,3-triazole ligand for the detection of Cu<sup>2+</sup> ions and, aqueous and gaseous hydrogen sulfide was investigated. The 4-(2-pyridyl)-1,2,3-triazole ligand functions both as an antenna chromophore and a receptor for Cu<sup>2+</sup> ions; the Cu<sup>2+</sup> complex was shown to be a chemosensor for the detection of aqueous hydrogen sulfide. The chemosensor exhibited significant reversibility over multiple cycles, observed with the sequential addition of Na<sub>2</sub>S followed by Cu<sup>2+</sup> ions. The limit of detection for aqueous hydrogen sulfide was 0.63 μM (20 ppb). No luminescent changes of the bimetallic terbium(III)/copper(II) complex were observed in the presence of gaseous hydrogen sulfide, and thus this sensor can only be used for the detection of aqueous hydrogen sulfide.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2818-2826"},"PeriodicalIF":2.2,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552447/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142635877","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
Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines. 咪唑并[1,2-a]嘧啶新衍生物的合成和抗霉菌活性。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-05 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.236
Dmitriy Yu Vandyshev, Daria A Mangusheva, Khidmet S Shikhaliev, Kirill A Scherbakov, Oleg N Burov, Alexander D Zagrebaev, Tatiana N Khmelevskaya, Alexey S Trenin, Fedor I Zubkov
{"title":"Synthesis and antimycotic activity of new derivatives of imidazo[1,2-<i>a</i>]pyrimidines.","authors":"Dmitriy Yu Vandyshev, Daria A Mangusheva, Khidmet S Shikhaliev, Kirill A Scherbakov, Oleg N Burov, Alexander D Zagrebaev, Tatiana N Khmelevskaya, Alexey S Trenin, Fedor I Zubkov","doi":"10.3762/bjoc.20.236","DOIUrl":"https://doi.org/10.3762/bjoc.20.236","url":null,"abstract":"<p><p>The heterocyclic core of imidazo[1,2-<i>a</i>]pyrimidine was formed in satisfactory yields as a result of the interaction of the readily available 2-aminoimidazole with <i>N</i>-substituted maleimides or <i>N</i>-arylitaconimides. The mechanism of the studied processes was postulated basing on experimental data, HPLC-MS analysis of reaction mixtures, and quantum chemical calculations. Molecular docking results of the obtained imidazo[1,2-<i>a</i>]pyrimidines, when compared with voriconazole, a drug already in clinical use, suggest that they may possess antifungal activity against <i>Candida albicans</i>.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2806-2817"},"PeriodicalIF":2.2,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552434/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614095","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
Mechanochemical difluoromethylations of ketones. 酮的机械化学二氟甲基化反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-04 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.235
Jinbo Ke, Pit van Bonn, Carsten Bolm
{"title":"Mechanochemical difluoromethylations of ketones.","authors":"Jinbo Ke, Pit van Bonn, Carsten Bolm","doi":"10.3762/bjoc.20.235","DOIUrl":"https://doi.org/10.3762/bjoc.20.235","url":null,"abstract":"<p><p>We present a mechanochemical synthesis of difluoromethyl enol ethers. Utilizing an in situ generation of difluorocarbenes, ketones are efficiently converted to the target products under solvent-free conditions. The reactions proceed at room temperature and are complete within 90 minutes, demonstrating both efficiency and experimental simplicity.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2799-2805"},"PeriodicalIF":2.2,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552444/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142635878","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
C-C Coupling in sterically demanding porphyrin environments. 立体要求苛刻的卟啉环境中的 C-C 偶联。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-04 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.234
Liam Cribbin, Brendan Twamley, Nicolae Buga, John E O' Brien, Raphael Bühler, Roland A Fischer, Mathias O Senge
{"title":"C-C Coupling in sterically demanding porphyrin environments.","authors":"Liam Cribbin, Brendan Twamley, Nicolae Buga, John E O' Brien, Raphael Bühler, Roland A Fischer, Mathias O Senge","doi":"10.3762/bjoc.20.234","DOIUrl":"https://doi.org/10.3762/bjoc.20.234","url":null,"abstract":"<p><p>Unlike their planar counterparts, classic synthetic protocols for C-C bond forming reactions on nonplanar porphyrins are underdeveloped. The development of C-C bond forming reactions on nonplanar porphyrins is critical in advancing this field of study for more complex porphyrin architectures, which could be used in supramolecular assemblies, catalysis, or sensing. In this work a library of arm-extended dodecasubstituted porphyrins was synthesized through the optimization of the classic Suzuki-Miyaura coupling of peripheral haloaryl substituents with a range of boronic acids. We report on palladium-catalyzed coupling attempts on the <i>ortho</i>-, <i>meta</i>-, and <i>para</i>-meso-phenyl position of sterically demanding dodecasubstituted saddle-shaped porphyrins. While <i>para-</i> and <i>meta-</i>substitutions could be achieved, <i>ortho</i>-functionalization in these systems remains elusive. Furthermore, borylation of a dodecasubstituted porphyrin's meso-phenyl position was explored and a subsequent C-C coupling showed the polarity of the reaction can be reversed resulting in higher yields. X-ray analysis of the target compounds revealed the formation of supramolecular assemblies, capable of accommodating substrates in their void.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2784-2798"},"PeriodicalIF":2.2,"publicationDate":"2024-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552435/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614065","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
Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction. 基于 [1,3]- 质子转移反应获得光学活性四氟乙烯胺。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-01 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.233
Yuta Kabumoto, Eiichiro Yoshimoto, Bing Xiaohuan, Masato Morita, Motohiro Yasui, Shigeyuki Yamada, Tsutomu Konno
{"title":"Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction.","authors":"Yuta Kabumoto, Eiichiro Yoshimoto, Bing Xiaohuan, Masato Morita, Motohiro Yasui, Shigeyuki Yamada, Tsutomu Konno","doi":"10.3762/bjoc.20.233","DOIUrl":"10.3762/bjoc.20.233","url":null,"abstract":"<p><p>Treatment of various (<i>R</i>)-<i>N</i>-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent <i>N</i>-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2776-2783"},"PeriodicalIF":2.2,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11533114/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575215","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
Copper-catalyzed yne-allylic substitutions: concept and recent developments. 铜催化的炔烯丙基置换：概念和最新进展。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-31 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.232
Shuang Yang, Xinqiang Fang
{"title":"Copper-catalyzed yne-allylic substitutions: concept and recent developments.","authors":"Shuang Yang, Xinqiang Fang","doi":"10.3762/bjoc.20.232","DOIUrl":"10.3762/bjoc.20.232","url":null,"abstract":"<p><p>The catalytic (asymmetric) allylation and propargylation have been established as powerful strategies allowing access to enantioenriched α-chiral alkenes and alkynes. In this context, combining allylic and propargylic substitutions offers new opportunities to expand the scope of transition metal-catalyzed substitution reactions. Since its discovery in 2022, copper-catalyzed yne-allylic substitution has undergone rapid development and significant progress has been made using the key copper vinyl allenylidene intermediates. This review summarizes the developments and illustrates the influences of copper salt, ligand, and substitution pattern of the substrate on the regioselectivity and stereoselectivity.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2739-2775"},"PeriodicalIF":2.2,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11533123/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575206","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
Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions. 芘衍生物与阳离子[60]富勒烯在磷脂膜中的相互作用及其对光动力作用的影响。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-30 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.231
Hayato Takagi, Çetin Çelik, Ryosuke Fukuda, Qi Guo, Tomohiro Higashino, Hiroshi Imahori, Yoko Yamakoshi, Tatsuya Murakami
{"title":"Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions.","authors":"Hayato Takagi, Çetin Çelik, Ryosuke Fukuda, Qi Guo, Tomohiro Higashino, Hiroshi Imahori, Yoko Yamakoshi, Tatsuya Murakami","doi":"10.3762/bjoc.20.231","DOIUrl":"10.3762/bjoc.20.231","url":null,"abstract":"<p><p>We have reported that upon visible light irradiation, ferrocene-porphyrin-[60]fullerene triad molecules yield long-lived charge-separated states, enabling the control of the plasma membrane potential (<i>V</i> <sub>m</sub>) in living cells. These previous studies indicated that the localization of the triad molecules in a specific intra-membrane orientation and the suppression of the photodynamic actions of the [60]fullerene (C<sub>60</sub>) moiety are likely important to achieve fast and safe control of <i>V</i> <sub>m</sub>, respectively. In this study, by mimicking our previous system of triad molecules and living cells, we report a simplified model system with a cationic C<sub>60</sub> derivative (catC<sub>60</sub>) and a liposome with embedded 1-pyrenebutyric acid (PyBA) to demonstrate that the addition of PyBA was important to achieve fast and safer control of <i>V</i> <sub>m</sub>.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2732-2738"},"PeriodicalIF":2.2,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11533121/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575242","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
Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light. 以可见光为媒介，通过一步法多步骤合成螺吲哚啉。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-29 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.230
Francesco Gambuti, Jacopo Pizzorno, Chiara Lambruschini, Renata Riva, Lisa Moni
{"title":"Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light.","authors":"Francesco Gambuti, Jacopo Pizzorno, Chiara Lambruschini, Renata Riva, Lisa Moni","doi":"10.3762/bjoc.20.230","DOIUrl":"10.3762/bjoc.20.230","url":null,"abstract":"<p><p>Spiro-heterocyclic indolenines are privileged scaffolds widely present in numerous indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of <i>N</i>-aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which reacts with an isocyanide and an electron-rich aniline in a three-component Ugi-type reaction to give an α-aminoamidine. This compound might undergo an additional visible light-mediated oxidation to furnish a second iminium intermediate, which acts as electrophile in an intramolecular electrophilic aromatic substitution giving the final spiro-indolenine. The scope of the process has been investigated with respect to all three components. Simple operations, mild conditions, and good yields make this strategy a convenient and sustainable way to obtain novel spiro-indolenine derivatives.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2722-2731"},"PeriodicalIF":2.2,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11533113/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575248","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
Young investigators in natural products chemistry, biosynthesis, and enzymology. 天然产品化学、生物合成和酶学领域的年轻研究人员。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-10-29 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.229
Jeffrey D Rudolf, Lena Barra, Takayoshi Awakawa
{"title":"Young investigators in natural products chemistry, biosynthesis, and enzymology.","authors":"Jeffrey D Rudolf, Lena Barra, Takayoshi Awakawa","doi":"10.3762/bjoc.20.229","DOIUrl":"https://doi.org/10.3762/bjoc.20.229","url":null,"abstract":"","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2720-2721"},"PeriodicalIF":2.2,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11533118/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142575253","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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