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C-H Trifluoromethylthiolation of aldehyde hydrazones. 醛肼的 C-H 三氟甲基硫代反应。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-12 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.242
Victor Levet, Balu Ramesh, Congyang Wang, Tatiana Besset
{"title":"C-H Trifluoromethylthiolation of aldehyde hydrazones.","authors":"Victor Levet, Balu Ramesh, Congyang Wang, Tatiana Besset","doi":"10.3762/bjoc.20.242","DOIUrl":"10.3762/bjoc.20.242","url":null,"abstract":"<p><p>The selective C-H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C-SCF<sub>3</sub> bond was achieved under oxidative and mild reaction conditions in the presence of the readily available AgSCF<sub>3</sub> salt via a one-pot sequential process (28 examples, up to 91% yield). Mechanistic investigations revealed that AgSCF<sub>3</sub> was the active species in the transformation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2883-2890"},"PeriodicalIF":2.2,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11571951/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667110","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 pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions. 通过基于异氰酸酯的多组分反应合成吡咯融合二苯并氧氮杂卓/二苯并硫氮杂卓/三唑并二氮杂卓衍生物。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-11 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.241
Marzieh Norouzi, Mohammad Taghi Nazeri, Ahmad Shaabani, Behrouz Notash
{"title":"Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions.","authors":"Marzieh Norouzi, Mohammad Taghi Nazeri, Ahmad Shaabani, Behrouz Notash","doi":"10.3762/bjoc.20.241","DOIUrl":"10.3762/bjoc.20.241","url":null,"abstract":"<p><p>An efficient and facile synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives was developed through the isocyanide-based multicomponent reaction of isocyanides, <i>gem</i>-diactivated olefins, and cyclic imines such as dibenzoxazepine, dibenzothiazepine, and triazolobenzodiazepine under solvent- and catalyst-free conditions. Purposefully, this approach produced various bioactive scaffolds using environmentally friendly, mild, and simple conditions. Due to their bioactive moieties, these compounds with exclusive fluorescence properties may attract great attention in biomedical applications, clinical diagnostics, and conjugate materials.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2870-2882"},"PeriodicalIF":2.2,"publicationDate":"2024-11-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11571948/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142667136","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
N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity. 靛蓝、靛红和异靛蓝的 N-糖苷：蓝色、红色和黄色糖及其抗癌活性。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-08 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.240
Peter Langer
{"title":"<i>N</i>-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity.","authors":"Peter Langer","doi":"10.3762/bjoc.20.240","DOIUrl":"https://doi.org/10.3762/bjoc.20.240","url":null,"abstract":"<p><p>Indigo, indirubin, and isoindigo derivatives have been used for centuries as pigments. Since the 1990s, a new aspect of the chemistry of this type of compounds is their activity against various types of cancer. <i>N</i>-Glycosides of indigo, indirubin, and isoindigo, blue, red, and yellow sugars, turned out to be of special interest because of their high cancerostatic activity and structural novelty. The present article provides an account on the synthesis and anticancer activity of these compounds.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2840-2869"},"PeriodicalIF":2.2,"publicationDate":"2024-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552416/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614056","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
Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides. 使用由烷基溴化物生成的有机锌试剂多组分合成 α-支链胺。
IF 2.2 4区 化学
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-07 eCollection Date: 2024-01-01 DOI: 10.3762/bjoc.20.239
Baptiste Leroux, Alexis Beaufils, Federico Banchini, Olivier Jackowski, Alejandro Perez-Luna, Fabrice Chemla, Marc Presset, Erwan Le Gall
{"title":"Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides.","authors":"Baptiste Leroux, Alexis Beaufils, Federico Banchini, Olivier Jackowski, Alejandro Perez-Luna, Fabrice Chemla, Marc Presset, Erwan Le Gall","doi":"10.3762/bjoc.20.239","DOIUrl":"https://doi.org/10.3762/bjoc.20.239","url":null,"abstract":"<p><p>The use of alkylzinc bromides in the multicomponent Mannich reaction is described. Heteroleptic organozinc compounds were obtained in THF or 2-MeTHF by direct insertion of zinc dust into the C-Br bond of alkyl bromides. It was found that the presence of a stoichiometric amount of LiCl was essential for the efficiency of the subsequent three-component coupling with aldehydes and amines. A variety of primary, secondary, and tertiary organozinc reagents as well as secondary amines and aromatic aldehydes could be used for the straightforward preparation of α-branched amines. Interestingly, whereas previously reported work describing the preparation and reaction of organozinc iodides in acetonitrile showed higher reactivity of secondary organozinc reagents over primary ones, reactions in THF in the presence of LiCl led to opposite results, with higher reactivity of primary organozinc reagents.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2834-2839"},"PeriodicalIF":2.2,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11552408/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142614071","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 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
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