{"title":"Synthesis of 3-acylated 1-aminoisoquinolin-4-ols <i>via</i> construction of a fully substituted pyridine moiety.","authors":"Nayeon Kim, Sunhee Lee, Ikyon Kim","doi":"10.1039/d6ob00919k","DOIUrl":"10.1039/d6ob00919k","url":null,"abstract":"<p><p>Described herein is an annulative functionalization approach to synthesize the 3-acylated 1-aminoisoquinolin-4-ol skeleton from a base-catalyzed reaction of 2-formylbenzonitrile with α-azidoketone under mild conditions, enabling the facile assembly of a fully functionalized aminopyridinol moiety <i>via</i> a domino procedure involving an aldol reaction, imine formation, tautomerization, and cycloisomerization.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8126-8138"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149072946","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}
Xiao Yu, Yongzheng Yin, Xian Liu, Yiping Liu, Yafei Ji
{"title":"Iodide-mediated electrochemical cyclization and desulfurization of <i>N</i>-substituted 3-aminoprop-2-enethioamides.","authors":"Xiao Yu, Yongzheng Yin, Xian Liu, Yiping Liu, Yafei Ji","doi":"10.1039/d6ob01379a","DOIUrl":"10.1039/d6ob01379a","url":null,"abstract":"<p><p>The synthesis of 5-aminoisothiazoles typically relies on toxic oxidants, transition metals, or harsh conditions. A green electrochemical method that enables the oxidative cyclization of readily available <i>N</i>-substituted 3-aminoprop-2-enethioamides (generated <i>in situ</i> from isothiocyanates and β-enamines) under constant current without the need for external chemical oxidants is reported herein. A broad range of 5-aminoisothiazoles are obtained in moderate to good yields (up to 85%, 30 examples) with high atom economy. Remarkably, when nucleophiles (<i>e.g.</i>, alcohols, water, and TMSN<sub>3</sub>) are present, the reaction switches to desulfurization, affording imidates, amides, or tetrazoles in good yields. Mechanistic studies support an anodic oxidation of iodide to iodine, which triggers cyclization and desulfurization. This work provides a mild and sustainable alternative to classical isothiazole synthesis and offers a tunable desulfurization platform.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8148-8153"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149079023","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}
{"title":"K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> promoted <i>N</i>-methoxymethylation of benzamides.","authors":"Deepak Gautam, Rinkle, Barun Jana","doi":"10.1039/d6ob01267a","DOIUrl":"https://doi.org/10.1039/d6ob01267a","url":null,"abstract":"<p><p>Herein, we report a potassium persulfate (K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>) promoted methodology for the selective <i>N</i>-methoxymethylation of benzamides. Utilizing methanol as both the solvent and a sustainable C1 source, the developed protocol exhibits broad functional group tolerance with good to excellent yields. The deuterium-labelling experiment and reported literature suggest a radical-mediated pathway, offering a green, operationally simple approach for the synthesis of <i>N</i>-methoxymethylated benzamides.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177888","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}
Tamilselvan Duraisamy, Vijay Thavasianandam Seenivasan, Pushparaj Palani, Karthick Govindan, Chetan Naik Sugali, Amjath Alikhan Ibrahim, Eldose V Varghese, Chih-Ming Chou, Sodio C N Hsu, Chia-Hsiang Chen, Gopal Chandru Senadi, Wei-Yu Lin
{"title":"Visible light photoredox-catalyzed difunctionalization of electron-deficient alkenes with <i>tert</i>-butyl nitrite: oxocarboxylic acid as an acyl source.","authors":"Tamilselvan Duraisamy, Vijay Thavasianandam Seenivasan, Pushparaj Palani, Karthick Govindan, Chetan Naik Sugali, Amjath Alikhan Ibrahim, Eldose V Varghese, Chih-Ming Chou, Sodio C N Hsu, Chia-Hsiang Chen, Gopal Chandru Senadi, Wei-Yu Lin","doi":"10.1039/d6ob01297c","DOIUrl":"https://doi.org/10.1039/d6ob01297c","url":null,"abstract":"<p><p>We report a visible-light photoredox-catalyzed acylative oximation of electron-deficient alkenes using <i>tert</i>-butyl nitrite and α-oxocarboxylic acids, providing direct access to β-keto oxime derivatives under mild conditions. The protocol combines <i>tert</i>-butyl nitrite as an NO donorwith acyl radicals generated through photoredox-mediated decarboxylation of α-oxocarboxylic acids. Vinyl sulfones and several other activated alkenes undergo the transforamtion to afford the corresponding products in moderate yields. Preliminary mechanistic studies support the involvement of acyl radical intermediates. The transformation can also be implemented under continuous photoflow conditions, demonstrating the operational adaptability of the protocol.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177903","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}
{"title":"Photocatalyst-free, visible-light-induced borylation and selenylation of aryltriazenes.","authors":"Thi Khanh Huyen Nghe, Hee-Kwon Kim","doi":"10.1039/d6ob01306f","DOIUrl":"10.1039/d6ob01306f","url":null,"abstract":"<p><p>Organoboron compounds, particularly arylboronate esters, are indispensable building blocks in organic synthesis and serve as key intermediates in chemical reactions for the preparation of pharmaceuticals, agrochemicals, and functional materials. In this study, a novel visible-light-driven borylation of aryltriazenes for the synthesis of arylboronate esters is described. Aryltriazenes were reacted with bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>) in the presence of trifluoroacetic acid as an additive under blue LED irradiation without requiring transition-metal catalysts. Using this protocol, a broad range of arylboronate esters were successfully synthesized under mild conditions. The protocol was extended to C-Se bond formation using diphenyl diselenide, providing unsymmetrical diaryl selenides. Overall, this method represents a promising and sustainable approach for the functionalization of aryltriazenes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8120-8125"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149056645","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}
{"title":"An alternative route for the total synthesis of gymnothelignan L.","authors":"Xinyu Liang, Zhiyu Zhang, Shuyang Luan, Zhengyi Qin, Jiaqi Zhuang, Zixu Zhang, Huilin Li, Xuegong She","doi":"10.1039/d6ob01371f","DOIUrl":"https://doi.org/10.1039/d6ob01371f","url":null,"abstract":"<p><p>Gymnothelignan L is a representative dibenzocyclooctene-type member of a large class of novel gymnothelignan natural products. We have previously achieved its first total synthesis by developing a bioinspired Friedel-Crafts cyclization approach. Herein, we report a second-generation synthesis to serve as an alternative synthetic route to gymnothelignan L through intramolecular dehydration and Friedel-Crafts cyclization from a linear gymnothelignan precursor with a C9 alcohol and a C6 aldehyde.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149177906","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}
Shashikant Tiwari, Shiva Pandey, Mahendra Nath, Diwan S Rawat
{"title":"Stereoselective transformation of alkynes to (<i>Z</i>)-β-deuterated vinyl sulfones using phosphoryl radical as a halogen atom transfer agent.","authors":"Shashikant Tiwari, Shiva Pandey, Mahendra Nath, Diwan S Rawat","doi":"10.1039/d6ob00980h","DOIUrl":"10.1039/d6ob00980h","url":null,"abstract":"<p><p>Herein, we report a one-pot, two-step, phosphoryl radical-mediated reductive deutero-dehalogenation of <i>in situ</i>-generated halo vinyl sulfones, enabling straightforward access to various β-deuterated vinyl sulfones using relatively inexpensive D<sub>2</sub>O as the deuterium source. This methodology directly transforms alkynes into thermodynamically less stable <i>Z</i>-Michael acceptors with substantial deuterium incorporation under environmentally benign conditions. Additionally, it tolerates a variety of functional groups, and halogen atom transfer from the vinylic position demonstrates excellent chemoselectivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8101-8107"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149035585","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}
Jordan Loughlin, Robert B P Elmes, Trinidad Velasco-Torrijos
{"title":"Glycopeptidomimetics: an underexplored tool in carbohydrate and peptide chemistry.","authors":"Jordan Loughlin, Robert B P Elmes, Trinidad Velasco-Torrijos","doi":"10.1039/d6ob01146b","DOIUrl":"10.1039/d6ob01146b","url":null,"abstract":"<p><p>Glycopeptidomimetics are structurally modified analogues of glycopeptides incorporating non-natural peptide-like scaffolds bearing native or modified glycan motifs. Glycopeptides, glycomimetics and peptidomimetics have each been extensively investigated across chemical biology and medicinal chemistry, however the intersection of these fields remains comparatively underexplored. This is surprising given the growing interest in carbohydrate-based recognition, targeting and therapeutic strategies, particularly in the context of cancer, infection and antimicrobial resistance. The replacement or modification of the native peptide component of glycopeptides offers glycopeptidomimetics opportunities to tune stability, conformation, multivalent presentation and biological activity, while retaining the molecular recognition features associated with carbohydrate structures. This review provides an overview of the synthesis and applications of glycopeptidomimetics reported to date, including glycopeptoids, glycodepsipeptides and other carbohydrate-containing peptidomimetic systems. Key successes, current limitations and emerging design principles are discussed, with particular emphasis on how this underdeveloped class of glycoconjugates may contribute to future advances in therapeutic discovery, diagnostics and chemical biology.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8044-8055"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149068640","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}
Sinduja Mohanraj, Ilene M Varghese, Sri Dinesh M, Arjun V, Meghna Mani, Takashi Ohshima, Amrita Das
{"title":"Benzylic C-N bond formation of xanthenes <i>via</i> copper-catalyzed cross dehydrogenative coupling.","authors":"Sinduja Mohanraj, Ilene M Varghese, Sri Dinesh M, Arjun V, Meghna Mani, Takashi Ohshima, Amrita Das","doi":"10.1039/d6ob01190j","DOIUrl":"10.1039/d6ob01190j","url":null,"abstract":"<p><p>Benzylic C-H bond functionalization of xanthene is reported by using copper iodide catalyst under oxidative condition. This methodology involves the C-N bond formation of xanthene at 9-position by using several <i>N</i>-nucleophiles such as carbamates, amides and sulfonamides. Further product transformation showcases the synthetic utility of amidation product. A plausible mechanism proposed the formation of cationic xanthene at 9-position.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8083-8087"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149072901","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}
Yanjun Xie, Yi Liang, Xinbo Liu, Jiangtao Gong, Huan Tang, Yunfeng Liao, Subarna Jyoti Kalita, Bing Yi, Jian-Ping Tan
{"title":"CuI-catalyzed cascade cyclization using indole-3-carbaldehydes and amidines for the synthesis of pyrimido[4,5-<i>b</i>]indoles.","authors":"Yanjun Xie, Yi Liang, Xinbo Liu, Jiangtao Gong, Huan Tang, Yunfeng Liao, Subarna Jyoti Kalita, Bing Yi, Jian-Ping Tan","doi":"10.1039/d6ob01213b","DOIUrl":"10.1039/d6ob01213b","url":null,"abstract":"<p><p>We report a copper-catalyzed cascade cyclization for the concise synthesis of pyrimido[4,5-<i>b</i>]indole skeletons <i>via</i> direct C-H functionalization and concomitant C-N bond formation. This methodology utilizes an inexpensive catalytic system (CuI/2,2'-bipyridine). The reaction demonstrates remarkable functional group tolerance and consistently delivers the target heterocycles in good to excellent yields. The insights gained from our studies are expected to advance general efforts towards the efficient synthesis of biology-oriented privileged heterocyclic skeletons.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"8066-8070"},"PeriodicalIF":2.8,"publicationDate":"2026-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101154","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}