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The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic anhydrides: an unusual approach to pyrrolo[3,4-c]pyridine derivatives, possessing anti-inflammatory activity.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-27 DOI: 10.1039/d5ob00040h
Vladimir P Zaytsev, Daria N Simakova, Viktoria S Maslova, Valentina V Ilyushenkova, Roman A Novikov, Mikhail S Grigoriev, Roman D Danilov, Roman Litvinov, Irina A Kolesnik, Vladimir I Potkin, Fedor I Zubkov
{"title":"The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic anhydrides: an unusual approach to pyrrolo[3,4-<i>c</i>]pyridine derivatives, possessing anti-inflammatory activity.","authors":"Vladimir P Zaytsev, Daria N Simakova, Viktoria S Maslova, Valentina V Ilyushenkova, Roman A Novikov, Mikhail S Grigoriev, Roman D Danilov, Roman Litvinov, Irina A Kolesnik, Vladimir I Potkin, Fedor I Zubkov","doi":"10.1039/d5ob00040h","DOIUrl":"https://doi.org/10.1039/d5ob00040h","url":null,"abstract":"<p><p>An unexpected cascade of <i>N</i>-acylation/intramolecular [4 + 2] cycloaddition/decarboxylation/isoxazole ring-opening reactions is observed in the course of the interaction between 3-(isoxazol-3-yl)allylamines and maleic or trifluoromethylmaleic anhydrides. This four-step sequence begins with the initial <i>N</i>-acylation of allylamines by the anhydride, followed by an intramolecular Diels-Alder reaction, which is accompanied by spontaneous decarboxylation, and ends with the opening of the isoxazole ring. As a result, an original approach to a pyrrolo[3,4-<i>c</i>]pyridine core was discovered. A test series of pyrrolo[3,4-<i>c</i>]pyridin-3-ones was investigated for anti-inflammatory activity and cytotoxicity, including the ability to inhibit NLRP3 inflammasome activation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143717699","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Synthesis of indole-linked β-cyano-enones: a pathway to indolyl-2-pyrrolones.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-27 DOI: 10.1039/d5ob00328h
Nurabul Mondal, Vidya Kumari, Danish Ali, Lokman H Choudhury
{"title":"Synthesis of indole-linked β-cyano-enones: a pathway to indolyl-2-pyrrolones.","authors":"Nurabul Mondal, Vidya Kumari, Danish Ali, Lokman H Choudhury","doi":"10.1039/d5ob00328h","DOIUrl":"https://doi.org/10.1039/d5ob00328h","url":null,"abstract":"<p><p>Herein, we report for the first time an additive- and catalyst-free dehydrogenative multicomponent reaction of arylglyoxal, malononitrile, and indoles for the one-pot synthesis of indole-linked β-cyano-enones in DMF medium. The reaction was performed at 100 °C in DMF, forming one C-C single bond and one CC double bond in a single-flask. Furthermore, we developed an efficient method for the synthesis of indolyl-2-pyrrolones having a hydroxyl group-containing chiral carbon center from the β-cyano-enones using trifluoroacetic acid and water as reaction medium. The β-cyano-enones were also further transformed into indolyl-1,2-diketones <i>via</i> a base-mediated reaction, which yielded indolyl quinoxalines upon reaction with <i>o</i>-phenylenediamine (OPD).</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143717697","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
O-Acylation triggered γ-umpolung functionalization of electron-poor alkenyl sulfoxides for the synthesis of 3-allyl indoles.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-27 DOI: 10.1039/d5ob00112a
Wenjie Wei, Qiangrong Xie, Xiaoyu Li, Yuanyuan Xie, Hongwei Zhou
{"title":"<i>O</i>-Acylation triggered γ-umpolung functionalization of electron-poor alkenyl sulfoxides for the synthesis of 3-allyl indoles.","authors":"Wenjie Wei, Qiangrong Xie, Xiaoyu Li, Yuanyuan Xie, Hongwei Zhou","doi":"10.1039/d5ob00112a","DOIUrl":"https://doi.org/10.1039/d5ob00112a","url":null,"abstract":"<p><p>Indole scaffolds, which are important structural motifs in organic chemistry, have garnered sustained interest due to their prevalence in pharmaceuticals, agrochemicals, and natural products. This study establishes a novel umpolung activation strategy for γ-position functionalization of electron-poor alkenyl sulfoxides, generating allylidenesulfonium intermediates that are subsequently trapped by indoles, achieving the synthesis of 3-functionalized indoles. Further transformations and plausible mechanism were investigated.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143717695","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
A β-hairpin peptide derived from Aβ forms different oligomers in the crystal state and in aqueous solution.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/d5ob00296f
Jason Zhu, Adam G Kreutzer, Zhiwei Liu, Xingyue Li, Sabrina M Richter, Vojislava Pophristic, James S Nowick
{"title":"A β-hairpin peptide derived from Aβ forms different oligomers in the crystal state and in aqueous solution.","authors":"Jason Zhu, Adam G Kreutzer, Zhiwei Liu, Xingyue Li, Sabrina M Richter, Vojislava Pophristic, James S Nowick","doi":"10.1039/d5ob00296f","DOIUrl":"https://doi.org/10.1039/d5ob00296f","url":null,"abstract":"<p><p>The supramolecular assembly of amyloid-β into soluble oligomers is critical Alzheimer's disease (AD) progression. Soluble Aβ oligomers have emerged as neurotoxic species involved in AD progression and some Aβ oligomers are thought to be composed of β-hairpins. In this work, we report the X-ray crystallographic and solution-phase assembly of a macrocyclic β-hairpin peptide that mimics a β-hairpin formed by Aβ<sub>16-36</sub>. In the crystal lattice, the peptide assembles into a symmetric hexamer composed of two identical triangular trimers. In aqueous solution, the peptide assembles to form an asymmetric hexamer. <sup>1</sup>H NMR, TOCSY, and <sup>1</sup>H,<sup>15</sup>N HSQC experiments establish that the asymmetric hexamer contains two different species, A and B. <sup>15</sup>N-edited NOESY reveals that species A is a cylindrin-like trimer and species B is a triangular trimer that collectively constitute the asymmetric hexamer. Diffusion-ordered NMR spectroscopy (DOSY) suggests that two asymmetric hexamers further assemble to form a dodecamer. NMR-guided molecular mechanics and molecular dynamics studies provide a model for the asymmetric hexamer and suggest how two asymmetric hexamers can form a dodecamer. Solution-phase NMR studies of analogues show that intermolecular hydrogen bonding and the formation of a hydrophobic core help stabilize the asymmetric hexamer. These NMR and crystallographic studies illustrate how an Aβ β-hairpin peptide can assemble to form different well-defined oligomers in the crystal state and in aqueous solution, providing a deeper understanding of the heterogeneity of Aβ oligomers and new structural models of Aβ oligomers composed of Aβ β-hairpins.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699075","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Visible-light-driven copper(II) catalysis for 2,3-disubstituted quinazolinone synthesis via Ullmann N-arylation and C-H oxidative amidation.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/d5ob00063g
Ahmed Th Abdulghaffar, Pei Hu, Yifan Hu, Chenxu Liu, Yanrong Ren, Zhongyan Cao, Yuanqing Xu, Min Jiang, Hao Xu
{"title":"Visible-light-driven copper(II) catalysis for 2,3-disubstituted quinazolinone synthesis <i>via</i> Ullmann <i>N</i>-arylation and C-H oxidative amidation.","authors":"Ahmed Th Abdulghaffar, Pei Hu, Yifan Hu, Chenxu Liu, Yanrong Ren, Zhongyan Cao, Yuanqing Xu, Min Jiang, Hao Xu","doi":"10.1039/d5ob00063g","DOIUrl":"https://doi.org/10.1039/d5ob00063g","url":null,"abstract":"<p><p>A novel visible-light-driven method for the synthesis of 2,3-disubstituted quinazolinones has been developed, employing copper(II) as a catalyst in a sequential Ullmann <i>N</i>-arylation and C-H oxidative amidation process. This methodology utilizes <i>o</i>-iodo-<i>N</i>-substituted benzamides and benzylamines as substrates, with molecular oxygen sourced from ambient air functioning as the oxidant. The reaction is conducted under mild conditions, utilizing cost-effective copper(II) chloride as the catalytic agent and Eosin Y as a photosensitizer, facilitated by blue LED irradiation. A broad compatibility with various substrates is demonstrated, yielding products in the range of 30% to 84%. Additionally, mechanistic studies elucidate a single-electron transfer pathway that incorporates aryl radical intermediates. This research presents a sustainable and efficient strategy for the synthesis of quinazolinones, with considerable synthetic and mechanistic implications.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699081","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Ni-catalyzed highly regioselective carboborylation bifunctionalization of allenes: access to α-substituted-γ-boro-δ-enoates.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/d5ob00364d
Jing Wu, Xinman Guo, Jinghan Zou, Ziyu Wang, Weixing Chang, Lingyan Liu, Jing Li
{"title":"Ni-catalyzed highly regioselective carboborylation bifunctionalization of allenes: access to α-substituted-γ-boro-δ-enoates.","authors":"Jing Wu, Xinman Guo, Jinghan Zou, Ziyu Wang, Weixing Chang, Lingyan Liu, Jing Li","doi":"10.1039/d5ob00364d","DOIUrl":"https://doi.org/10.1039/d5ob00364d","url":null,"abstract":"<p><p>A Ni-catalyzed highly regioselective carboborylation bifunctionalization of allenes was developed, and a series of α-substituted-γ-boro-δ-enoates were generated in good to high yields. This reaction has the advantages of mild reaction conditions, a wide substrate scope and good late-stage modification applications, providing a new strategy for the synthesis of configurationally defined trisubstituted vinyl boron compounds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143707764","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Advances in the selective functionalization of B(3,6)-H of o-carboranes.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/d4ob01778a
Ji Wu, Ke Cao
{"title":"Advances in the selective functionalization of B(3,6)-H of <i>o</i>-carboranes.","authors":"Ji Wu, Ke Cao","doi":"10.1039/d4ob01778a","DOIUrl":"https://doi.org/10.1039/d4ob01778a","url":null,"abstract":"<p><p>This review summarizes the methodologies for the selective functionalization of the B(3,6) vertices of <i>o</i>-carboranes, including the deboration-capitation reaction, the coupling reaction of B-X (X = I, Br) bonds, reactions of 1,3-dehydro-<i>o</i>-carborane and [3-N<sub>2</sub>-<i>o</i>-C<sub>2</sub>B<sub>10</sub>H<sub>11</sub>][BF<sub>4</sub>] as well as transition-metal-catalyzed B-H activation. These works offer a versatile toolbox for synthesizing B(3,6)-substituted <i>o</i>-carborane derivatives and will promote their applications in material science, pharmaceutical chemistry, and related disciplines.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699077","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Access to chiral phthalidyl ester prodrugs via an isothiourea-catalyzed dynamic kinetic resolution reaction.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/d4ob02057j
Hui Cai, Chaoyang Song, Dan Ling, Youlin Deng, Zhichao Jin, Tingting Li
{"title":"Access to chiral phthalidyl ester prodrugs <i>via</i> an isothiourea-catalyzed dynamic kinetic resolution reaction.","authors":"Hui Cai, Chaoyang Song, Dan Ling, Youlin Deng, Zhichao Jin, Tingting Li","doi":"10.1039/d4ob02057j","DOIUrl":"https://doi.org/10.1039/d4ob02057j","url":null,"abstract":"<p><p>An isothiourea-catalyzed acylative dynamic kinetic resolution reaction has been developed for the synthesis of chiral phthalidyl ester prodrugs. Various chiral phthalidyl esters were obtained in moderate to excellent yields (up to 97%) and good to excellent optical purities (up to 99 : 1 er). Notably, a variety of acyl chlorides were well tolerated, even those derived from pharmaceuticals, agrochemicals, and natural products. This catalytic transformation is an effective strategy for the development of chiral phthalidyl ester prodrugs.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699076","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Meyer-Schuster rearrangement/allylic alkenylation of propynolaldehydes with olefins to synthesize skipped 1,4-dienes.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/d5ob00173k
Cheng-Ping Shen, Hai-Tao Zhu, Guo-Hua Li, Xin Chang, Jia-Jun Xi, Ni-Ni Zhou, An-Xi Zhou
{"title":"Meyer-Schuster rearrangement/allylic alkenylation of propynolaldehydes with olefins to synthesize skipped 1,4-dienes.","authors":"Cheng-Ping Shen, Hai-Tao Zhu, Guo-Hua Li, Xin Chang, Jia-Jun Xi, Ni-Ni Zhou, An-Xi Zhou","doi":"10.1039/d5ob00173k","DOIUrl":"https://doi.org/10.1039/d5ob00173k","url":null,"abstract":"<p><p>A highly efficient method for the straightforward synthesis of skipped 1,4-dienes is presented <i>via p</i>-TsOH·H<sub>2</sub>O-catalyzed intramolecular intercepted Meyer-Schuster rearrangement/allylic alkenylation of propynolaldehydes with olefins in a one-pot manner. This cascade transformation is characterized by metal-free and mild conditions, extensive substrate applicability, atom economy, gram-scale production, and water as the sole by-product. Furthermore, the resulting functionalized 1,4-dienes could be derivatized by Fe(III)-promoted radical cyclization, allylic methoxylation under reductive conditions, and Pd(II)-catalyzed Sonogashira coupling.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699078","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Polynaphthoquinone mediated metal-free direct N-alkylation of (hetero)aryl amines using alcohols.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-03-25 DOI: 10.1039/d5ob00163c
Uttam Kumar Panigrahi, Vengadesh Kumara Mangalam Ramakrishnan
{"title":"Polynaphthoquinone mediated metal-free direct <i>N</i>-alkylation of (hetero)aryl amines using alcohols.","authors":"Uttam Kumar Panigrahi, Vengadesh Kumara Mangalam Ramakrishnan","doi":"10.1039/d5ob00163c","DOIUrl":"https://doi.org/10.1039/d5ob00163c","url":null,"abstract":"<p><p>Herein, we present polynaphthoquinone as an effective metal-free catalyst for the direct <i>N</i>-alkylation of aryl and heteroaryl amines using alcohols. Our experiments reveal that the optimal reaction conditions consist of 1.0 mmol of alcohol, 1.5 mmol of aniline, 0.8 equivalents of <i>t</i>-BuOK, and 30 wt% polynaphthoquinone catalyst in toluene at 135 °C under an inert atmosphere for 24 hours. Control experiments confirm that without a catalyst or base, the reaction fails to progress. Additionally, the reused catalyst in subsequent reactions yields good to excellent results. This methodology has also been extended to the dehydrogenative synthesis of quinolines and indoles.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699079","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
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