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Recent advances in visible-light-driven photocatalytic synthesis of biologically active N-heterocycles. 可见光驱动光催化合成生物活性n -杂环的研究进展。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-14 DOI: 10.1039/d5ob01411e
Surabhi Sinha, Praveen P Singh, Deepak Kumar, Vishal Srivastava
{"title":"Recent advances in visible-light-driven photocatalytic synthesis of biologically active N-heterocycles.","authors":"Surabhi Sinha, Praveen P Singh, Deepak Kumar, Vishal Srivastava","doi":"10.1039/d5ob01411e","DOIUrl":"https://doi.org/10.1039/d5ob01411e","url":null,"abstract":"<p><p>Heterocycles that contain nitrogen are a very significant class of chemicals that are employed extensively in medicinal chemistry, agrochemistry, and materials research. Thus, there is increasing interest in developing practical, effective, and eco-friendly synthetic processes for creating nitrogen-containing heterocycles. Using visible light as a catalyst for chemical reactions has drawn a lot of attention in recent years because of its inherent abundance, ease of use, and potential industrial applications. Based on the size and kind of N-heterocyclic rings that are produced, this article provides an overview of the synthesis of N-heterocycles utilising visible-light photoredox catalysis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145285136","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
Diastereoselective spirocyclopropanation of (E)-2-ylidene-3-cyclohexenones and sulfur ylides. (E)-2-酰基-3-环己酮和硫酰基的非对映选择性螺环丙烷化。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-14 DOI: 10.1039/d5ob01383f
Zheng-Yan Li, Xing Zheng, Yi-Na Ma, Mingwei Yuan, Yin Zhang, Lin Jiang, Minglong Yuan
{"title":"Diastereoselective spirocyclopropanation of (<i>E</i>)-2-ylidene-3-cyclohexenones and sulfur ylides.","authors":"Zheng-Yan Li, Xing Zheng, Yi-Na Ma, Mingwei Yuan, Yin Zhang, Lin Jiang, Minglong Yuan","doi":"10.1039/d5ob01383f","DOIUrl":"https://doi.org/10.1039/d5ob01383f","url":null,"abstract":"<p><p>A diastereoselective spirocyclopropanation reaction of (<i>E</i>)-2-ylidene-3-cyclohexenones and stabilized sulfur ylides is reported. This [2 + 1] annulation reaction enables rapid and efficient assembly of a series of spirocyclopropyl 3-cyclohexenones in fair to excellent yields and with high to excellent diastereoselectivity. The utility of this methodology is further showcased by a gram-scale reaction, as well as the construction of 2<i>H</i>-chromene, dihydrobenzofuran and chroman derivatives through readily operable cyclopropane ring-opening/cyclization reactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145285053","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
Base-promoted tandem synthesis of nitrogen-containing compounds: MN(SiMe3)2 as potential nitrogen sources. 碱促进含氮化合物串联合成：MN(SiMe3)2作为潜在氮源。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-14 DOI: 10.1039/d5ob01461a
Dong Zou, Jie Ying
{"title":"Base-promoted tandem synthesis of nitrogen-containing compounds: MN(SiMe<sub>3</sub>)<sub>2</sub> as potential nitrogen sources.","authors":"Dong Zou, Jie Ying","doi":"10.1039/d5ob01461a","DOIUrl":"https://doi.org/10.1039/d5ob01461a","url":null,"abstract":"<p><p>Metal silylamides [MN(SiMe<sub>3</sub>)<sub>2</sub>, M = Li, Na, and K] are widely used Brønsted bases and have become among the most prevalent bases in organic research owing to their commercial availability and low cost. MN(SiMe<sub>3</sub>)<sub>2</sub> exhibits strong basicity and high stability, making it a common deprotonation reagent for C-H bond activation. Nitrogen-containing compounds are ubiquitous in pharmaceuticals and natural products, rendering the synthesis of bioactive nitrogen-containing compounds a research priority. Traditionally, the synthesis of these compounds has relied on amines, but the importance of sustainable chemistry is increasing, and the development of efficient and atom-economical synthetic methodologies without compromising compound selectivity and environmental safety is a major theme of research today. In this review, we comprehensively summarize recent advances in the tandem synthesis of nitrogen-containing compounds mediated by MN(SiMe<sub>3</sub>)<sub>2</sub> under transition-metal-free conditions. Based on distinct reaction mechanisms, the tandem reactions are classified into two categories: those proceeding <i>via</i> imine intermediates and those involving silylamide intermediates. Moreover, the reaction conditions, functional group universality, reaction mechanism, and applications are discussed in detail, and the prospects and limitations of development in this field are also critically analyzed.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145285098","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
Recent advances in electrochemical C-H chalcogenation (O/S/Se) of heteroaromatics. 电化学C-H加氢反应（O/S/Se）研究进展。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-13 DOI: 10.1039/d5ob01450f
Xianhui You, Xiaotong Gao, Yuechuan Wang, Ke-Jin Jiao
{"title":"Recent advances in electrochemical C-H chalcogenation (O/S/Se) of heteroaromatics.","authors":"Xianhui You, Xiaotong Gao, Yuechuan Wang, Ke-Jin Jiao","doi":"10.1039/d5ob01450f","DOIUrl":"https://doi.org/10.1039/d5ob01450f","url":null,"abstract":"<p><p>Chalcogenated heteroaromatics containing C-O/S/Se bonds are widely prevalent in natural products, medicines, and bioactive structures, and numerous elegant methodologies for the direct synthesis of these compounds have been developed in an electrochemical C-H chalcogenation fashion, as it utilizes electrons as a clean, sustainable, and traceless reagent instead of transition metal oxidants or reductants. This review summarizes the recent advances (from 2017 to early 2025) in the fascinating field of electrochemical synthesis of chalcogenated heteroaromatics, which are categorized by the source of chalcogenides involved. The review aims to provide readers with a more comprehensive understanding of the advances in this exciting field.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145278450","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
Design, synthesis and characterization of a carbonyl-containing high-density pyrazolotriazine-based energetic compound. 含羰基高密度吡唑三嗪类含能化合物的设计、合成与表征。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-13 DOI: 10.1039/d5ob01264c
Huanyu Sun, Zhiwei Zeng, Chunhui Chen, Xiancheng Mai, Jia Wang, Wei Huang, Yongxing Tang, Yuji Liu
{"title":"Design, synthesis and characterization of a carbonyl-containing high-density pyrazolotriazine-based energetic compound.","authors":"Huanyu Sun, Zhiwei Zeng, Chunhui Chen, Xiancheng Mai, Jia Wang, Wei Huang, Yongxing Tang, Yuji Liu","doi":"10.1039/d5ob01264c","DOIUrl":"https://doi.org/10.1039/d5ob01264c","url":null,"abstract":"<p><p>Constructing novel high-energy frameworks to achieve an ideal balance between high energy density and good stability is a common goal in the field of energetic materials. In this study, a novel high-energy density compound was designed and synthesized by introducing carbonyl groups into a fused pyrazolotriazine. Its crystal structure shows that the compound formed compact planar stacking. A three-dimensional intermolecular network through hydrogen bonding and π-π interactions was constructed, resulting in its high density of 1.92 g cm<sup>-3</sup>. The compound possesses good detonation performances (detonation velocity: 8430 m s<sup>-1</sup>, detonation pressure: 28.5 GPa), a high decomposition temperature of 210 °C and low sensitivities (impact sensitivity >40 J, friction sensitivity >360 N), which are superior to those of conventional explosives like TNT. This study demonstrates the feasibility of introducing carbonyl groups into nitrogen-rich fused systems to achieve a balance between high energy and low sensitivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145278453","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
Decoding ortho regiospecificity and high endo stereoselectivity in pyrazole synthesis via the activation/strain model. 通过激活/应变模型解码吡唑合成中的邻位区域特异性和高内位立体选择性。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-13 DOI: 10.1039/d5ob01142f
Saeedreza Emamian, Ali Mohammad Shariati, Majid Salami, Antonio Frontera
{"title":"Decoding <i>ortho</i> regiospecificity and high <i>endo</i> stereoselectivity in pyrazole synthesis <i>via</i> the activation/strain model.","authors":"Saeedreza Emamian, Ali Mohammad Shariati, Majid Salami, Antonio Frontera","doi":"10.1039/d5ob01142f","DOIUrl":"https://doi.org/10.1039/d5ob01142f","url":null,"abstract":"<p><p>A comprehensive density functional theory investigation was conducted to elucidate the regio- and stereoselectivity of the 1,3-dipolar cycloaddition reaction (13-DCR) between a diazo compound (1,3-dipole D-1) and an electron-deficient nitroethylene derivative (dipolarophile Dph-2), which serves as the key initiating step in a recently reported domino synthesis of pyrazole derivatives. Experimentally performed in dichloromethane at 80 °C, the reaction exhibits exclusive formation of the <i>ortho</i> regioisomer. Calculated activation free energies and rate constants quantitatively reproduce the experimentally observed complete <i>ortho</i> regioselectivity and high <i>endo</i> stereoselectivity. Activation strain model (ASM) analysis reveals that the regioselectivity is primarily governed by stabilizing interaction energies. Subsequent energy decomposition analysis using the recently developed sobEDA method identifies orbital interactions, particularly HOMOD-1 to LUMODph-2 charge transfer, as the main contributors. The Extended Transition State-Natural Orbitals for Chemical Valence (ETS-NOCV) analysis confirms this dominant orbital interaction, rationalizing the <i>ortho</i> selectivity. The stereoselectivity favoring the <i>endo</i> pathway is attributed to lower total strain energy, mainly originating from the flexibility of the D-1 fragment. This combined computational study offers a detailed mechanistic understanding of the 13-DCR regio- and stereoselectivity, providing results in excellent agreement with experimental outcomes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145278488","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
One-pot three-component synthesis of benzo[h]isoquinolin-3-ones via rhodium(III)-catalyzed C-H activation. 铑催化C-H活化一锅三组分合成苯并[h]异喹啉-3-酮。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-13 DOI: 10.1039/d5ob01222h
Weihong Song, Xiaomei Jiang, Weiguo Yu, ZiWei Xiang
{"title":"One-pot three-component synthesis of benzo[<i>h</i>]isoquinolin-3-ones <i>via</i> rhodium(III)-catalyzed C-H activation.","authors":"Weihong Song, Xiaomei Jiang, Weiguo Yu, ZiWei Xiang","doi":"10.1039/d5ob01222h","DOIUrl":"https://doi.org/10.1039/d5ob01222h","url":null,"abstract":"<p><p>A Rh(III)-catalyzed one-pot synthesis of benzo[<i>h</i>]isoquinolin-3-ones from 1-naphthaldehyde, aniline and diazo compounds has been realized, with an imine serving as the directing group which was generated through aldimine condensation <i>in situ</i>. This concise protocol features low catalyst loading, excellent yield of products, and a broad substrate scope.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145278440","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
Recent advances in photo-induced synthesis of polycyclic quinazolinones from unactivated alkene-tethered quinazolinones. 非活化烯系喹啉酮光诱导合成多环喹唑啉酮的研究进展。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-13 DOI: 10.1039/d5ob01231g
Yu-Xin Luo, Fan-Lin Zeng, Teck-Peng Loh, Zhenhua Jia
{"title":"Recent advances in photo-induced synthesis of polycyclic quinazolinones from unactivated alkene-tethered quinazolinones.","authors":"Yu-Xin Luo, Fan-Lin Zeng, Teck-Peng Loh, Zhenhua Jia","doi":"10.1039/d5ob01231g","DOIUrl":"https://doi.org/10.1039/d5ob01231g","url":null,"abstract":"<p><p>In recent years, polycyclic quinazolinone derivatives have attracted considerable attention from the synthetic organic chemistry community owing to their diverse pharmacological and biological properties. This review comprehensively summarizes recent progress (2021-2025) in photoinduced synthesis of polycyclic quinazolinones <i>via</i> radical cascade cyclization or intramolecular hydroarylation of unactivated alkene-tethered quinazolinone precursors. These methods are systematically categorized into four distinct classes based on the photocatalytic system employed: metal-based photocatalysts, organic photocatalysts, semiconductor photocatalysts, and photocatalyst-free conditions. Mechanistic insights and substrate scope are discussed in detail to highlight the synthetic versatility and limitations of each approach. Furthermore, future directions are outlined, including the development of recyclable photocatalytic systems, substrate engineering, and the use of environmentally benign solvents. We hope this review will serve as a comprehensive and practical resource for researchers engaged in the synthesis of quinazolinone-based heterocycles and related photochemical transformations.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145278508","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
Photo-induced radical trifluoromethylation/dearomatization of 3-substituted indoles. 3-取代吲哚的光诱导自由基三氟甲基化/脱芳化。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-13 DOI: 10.1039/d5ob01103e
Yuyu Lv, Zhoubin Deng, Zhijun Zhu, Xiaopeng Hai, Junjiao Wang, Ke-Hu Wang, Danfeng Huang, Yulai Hu
{"title":"Photo-induced radical trifluoromethylation/dearomatization of 3-substituted indoles.","authors":"Yuyu Lv, Zhoubin Deng, Zhijun Zhu, Xiaopeng Hai, Junjiao Wang, Ke-Hu Wang, Danfeng Huang, Yulai Hu","doi":"10.1039/d5ob01103e","DOIUrl":"https://doi.org/10.1039/d5ob01103e","url":null,"abstract":"<p><p>A visible-light-induced cascade radical trifluoromethylation/cyclization/dearomatization reaction between 3-substituted indoles and CF<sub>3</sub>Br in the presence of 4CzIPN and K<sub>2</sub>CO<sub>3</sub> has been developed. This protocol provided a facile, efficient and cost-effective approach for the construction of 3,3-spirocyclic 2-trifluoromethylindolines in moderate to high yields under mild conditions. This process can be scaled up. A radical relay mechanism was proposed based on the control experiments. This protocol provides an efficient route for the synthesis of 3,3-spirocyclic 2-trifluoromethylindolines with the advantages of a broad substrate scope, a cheap trifluoromethyl source and a green source of energy.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145278456","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
Cu-catalyzed oxygen-transferring hydrazonation of enynones. 铜催化烯酮氧转移腙化反应。
IF 2.7 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-10-10 DOI: 10.1039/d5ob01444a
Shaotong Qiu, Yangxin Mao, Zhicheng Yang, Jiangan Liu, Yimin Shangguan, Xinlei Wang, Chun Zou, Yun-Hui Zhao, Baishu Zheng, Hu Zhou
{"title":"Cu-catalyzed oxygen-transferring hydrazonation of enynones.","authors":"Shaotong Qiu, Yangxin Mao, Zhicheng Yang, Jiangan Liu, Yimin Shangguan, Xinlei Wang, Chun Zou, Yun-Hui Zhao, Baishu Zheng, Hu Zhou","doi":"10.1039/d5ob01444a","DOIUrl":"https://doi.org/10.1039/d5ob01444a","url":null,"abstract":"<p><p>An unprecedented Cu-catalyzed oxygen-transferring hydrazonation reaction of enynones with arylsulfonylhydrazines has been developed. Featuring high efficiency, broad substrate scope and mild reaction conditions, this protocol provides a practical alcohol-free approach to access various bio-related aryl-alkenyl and aryl-aryl sulfonylhydrazones containing carbonyl groups in up to 97% yields, which are challenging to synthesize <i>via</i> conventional methods. The utility of this reaction is further demonstrated by transformation of the obtained molecules into diverse nitrogen-containing heterocyclic compounds and alkenyl or hydroxyl derivatives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145256886","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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