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Facile Access to Indolo[2,3-b]quinoline Alkaloids via DMSO-Mediated Cascade Cyclization: Unveiling Their Photophysical Potential 通过二甲基亚砜介导的级联环化制备吲哚[2,3-b]喹啉生物碱：揭示其光物理潜力
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-29 DOI: 10.1039/d5qo01193k
Gokulprasanth Nataraj, Ranjithkumar Chandran, Muniappan Kalipriyadharshini, Diksha Bansal, Easwaramoorthi Shanmugam, Mrinal Kanti Das, Saikat Chaudhuri
{"title":"Facile Access to Indolo[2,3-b]quinoline Alkaloids via DMSO-Mediated Cascade Cyclization: Unveiling Their Photophysical Potential","authors":"Gokulprasanth Nataraj, Ranjithkumar Chandran, Muniappan Kalipriyadharshini, Diksha Bansal, Easwaramoorthi Shanmugam, Mrinal Kanti Das, Saikat Chaudhuri","doi":"10.1039/d5qo01193k","DOIUrl":"https://doi.org/10.1039/d5qo01193k","url":null,"abstract":"A streamlined and efficient synthetic strategy has been established for the construction of Indolo[2,3-b]quinolines, utilizing C3-alkylated indole as the starting material and mediated by DMSO and HCl. This methodology enables the direct annulation of the quinoline ring onto a pre-functionalized indole core with high functional group compatibility. The reaction proceeds smoothly across a diverse range of substrates, delivering the desired products in consistently high yields. Its operational simplicity, scalability, and broad substrate scope highlight its practical utility, particularly for large-scale synthesis. Notably, this approach provides a valuable platform for the synthesis of complex natural products featuring the Indolo[2,3-b]quinoline framework. Indolo[2,3-b]quinolines show strong blue to blue-green fluorescence with large Stokes shifts due to excited-state proton transfer. Substituents on the pyrrolic nitrogen and aromatic core significantly affect absorption and emission by altering hydrogen bonding and photobasicity. Electron-donating groups at the 5-position increase fluorescence lifetime and quantum yield.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"20 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145183374","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
New mode of sulfur ylides reactivity: stereoelectronic control provides C–C bond insertion before cyclopropanation/epoxidation directly affording homologated three-membered rings 硫酰化物反应的新模式：立体电子控制在环丙烷化/环氧化之前提供C-C键插入，直接提供同构的三元环
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-29 DOI: 10.1039/d5qo01266j
Vitaly Shorokhov, Beauty K. Chabuka, Albina A Nikolaeva, Sergey S. Zhokhov, Ivan A. Andreev, Nina K. Ratmanova, Igor V. Trushkov, Olga Alexandrovna Ivanova, Igor Alabugin
{"title":"New mode of sulfur ylides reactivity: stereoelectronic control provides C–C bond insertion before cyclopropanation/epoxidation directly affording homologated three-membered rings","authors":"Vitaly Shorokhov, Beauty K. Chabuka, Albina A Nikolaeva, Sergey S. Zhokhov, Ivan A. Andreev, Nina K. Ratmanova, Igor V. Trushkov, Olga Alexandrovna Ivanova, Igor Alabugin","doi":"10.1039/d5qo01266j","DOIUrl":"https://doi.org/10.1039/d5qo01266j","url":null,"abstract":"Ylides are versatile reagents known for their dual electrophilic and nucleophilic reactivity, mimicking carbenes in many reactions. In this study, we uncover a previously unreported reactivity pathway for ylides: a methylene insertion into C–C bonds. We show that sulfur ylides can achieve homologation of alkenes and aldehydes before proceeding through the classical Corey–Chaykovsky reaction. This process allows for the dual transfer of CH₂ groups to both substrates, yielding benzylcyclopropanes and benzyloxiranes, valuable intermediates in organic synthesis. Remarkably, the same sulfur ylide reagent participates in two distinct carbene-like transformations within this cascade. Mechanistic studies reveal the role of a tightly coordinated stereoelectronic network playing a crucial role in facilitating anionic 1,2-aryl shifts.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"97 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145183066","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Enantioselective Organocatalytic Electrochemical α-Chlorination of Aldehydes 醛类的对映选择性有机催化α-氯化反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-26 DOI: 10.1039/d5qo01249j
Stefano Andolina, Alessandra Puglisi, Sergio Rossi, Fabrizio MEDICI, Maurizio Benaglia
{"title":"Enantioselective Organocatalytic Electrochemical α-Chlorination of Aldehydes","authors":"Stefano Andolina, Alessandra Puglisi, Sergio Rossi, Fabrizio MEDICI, Maurizio Benaglia","doi":"10.1039/d5qo01249j","DOIUrl":"https://doi.org/10.1039/d5qo01249j","url":null,"abstract":"The enantioselective organocatalytic α-chlorination of aldehydes using electrochemistry to activate the enamine intermediate through SOMO strategy was investigated. Based on mechanistic insights, an improved procedure was developed, that directly employs CuCl2 in the electrochemical reaction. Under the optimized setup (potentiostatic condition of 1 V, glassy-carbon electrodes, in a 0.2 M solution of LiClO4), in the presence of catalytic amounts of a chiral imidazolidinone as organocatalyst, the aldehyde reacts with copper chloride (II) and leads to the formation of the corresponding α-chlorinated aldehydes in high yields and high enantioselectivities (up to 97% ee). Thanks to the electrochemistry approach, stoichiometric amounts of chemical oxidants were successfully replaced by electrons, enabling a more sustainable and efficient, catalytic stereoselective reaction. In addition, the transformation was successfully translated to a continuous flow process, which significantly enhanced productivity and reduced the reaction time to 1.73 minutes only, and that was performed also on gram scale","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"31 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145141108","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Transition Metal-Free Transfer Hydrogenation of Aryl Azides with Alcohols: Direct Synthesis of Secondary Amines and N-Heterocycles 芳基叠氮化物与醇的无过渡金属转移加氢：仲胺和n -杂环的直接合成
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-25 DOI: 10.1039/d5qo01070e
Jinwoo Lee, Ramachandra Reddy Putta, Junhwa Hong, Seung Hyun Choi, Honghui Lee, Seok Beom Lee, Suckchang Hong
{"title":"Transition Metal-Free Transfer Hydrogenation of Aryl Azides with Alcohols: Direct Synthesis of Secondary Amines and N-Heterocycles","authors":"Jinwoo Lee, Ramachandra Reddy Putta, Junhwa Hong, Seung Hyun Choi, Honghui Lee, Seok Beom Lee, Suckchang Hong","doi":"10.1039/d5qo01070e","DOIUrl":"https://doi.org/10.1039/d5qo01070e","url":null,"abstract":"Organic azides and alcohols were harnessed in a transition metal-free, base-mediated transfer hydrogenation system, which offers an efficient synthetic route to secondary amines. In the presence of KO t Bu, aryl azides underwent hydrogen transfer with alcohols to produce secondary amines in high yields. The method features a broad substrate scope, gram-scale applicability, and straightforward experimental setup. Furthermore, N-heterocycles such as quinoxalines and quinolines were synthesized under similar reaction conditions. Mechanistic studies demonstrated that both alcohols and KO t Bu were essential for facilitating hydrogen transfer to azides. The exclusion of a radical pathway, confirmation of alcohol as the reductant, and deuterium labeling experiments provided key insights into the reaction mechanism. DFT calculations revealed that the reduction of azides proceeded through a six-membered cyclic transition state, resembling the mechanism proposed for the Meerwein-Ponndorf-Verley (MPV) reduction. Notably, the potassium cation stabilized the transition state by interacting with both the aryl group and the nitrogen atom of the aryl azide.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"41 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145133461","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Ru-Diphosphine catalyzed asymmetric hydrogenation of unprotected β-C-glycosidic ketones 钌二膦催化无保护β- c -糖苷酮的不对称加氢反应
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-25 DOI: 10.1039/d5qo01085c
Limin Xu, Yuxuan Zhang, Yan Lu, Zhaoguo Zhang
{"title":"Ru-Diphosphine catalyzed asymmetric hydrogenation of unprotected β-C-glycosidic ketones","authors":"Limin Xu, Yuxuan Zhang, Yan Lu, Zhaoguo Zhang","doi":"10.1039/d5qo01085c","DOIUrl":"https://doi.org/10.1039/d5qo01085c","url":null,"abstract":"Stereoselective reduction of β-<em>C</em>-glycosidic ketones is an effective method for the synthesis of carbohydrate derivatives. We herein report that β-<em>C</em>-glycosidic ketones, not generally considered as functionalized ketones, are unexpectedly hydrogenated by Ru-diphosphine catalysts with excellent stereoselectivity (up to &gt;99 : 1 dr). Further investigation into the effect of the chiral hydroxyl groups during the reaction has also been conducted. This reaction has been performed on a multi-gram scale, providing a novel approach for the construction of chiral centers in carbohydrate derivatives.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"94 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145134119","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Rh-catalyzed [3 + 2] cyclization of (hetero)cyclic 1,3-dicarbonyls with 2-aminoarylboronic esters to access carbazolones 铑催化[3 + 2]杂环1,3-二羰基与2-氨基羰基硼酯的环化反应得到咔唑酮
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-24 DOI: 10.1039/d5qo01079a
Bei Wan, Ce Liu, Haoyuan Xiong, Yi Deng, Zhonghua Gu, Shaoyu Mai, Feng Qiu, Qingfeng Du
{"title":"Rh-catalyzed [3 + 2] cyclization of (hetero)cyclic 1,3-dicarbonyls with 2-aminoarylboronic esters to access carbazolones","authors":"Bei Wan, Ce Liu, Haoyuan Xiong, Yi Deng, Zhonghua Gu, Shaoyu Mai, Feng Qiu, Qingfeng Du","doi":"10.1039/d5qo01079a","DOIUrl":"https://doi.org/10.1039/d5qo01079a","url":null,"abstract":"We report herein the first Suzuki-type [3 + 2] cyclization of cyclic 1,3-dicarbonyls with readily available 2-aminoarylboronic esters to synthesize carbazolones. With environmentally benign EtOH/H2O as solvent, a series of structurally and electronically diverse carbazolones can be readily obtained in a modular manner. This approach is mild, operationally simple, high-yield, scalable, and highly tolerant to moisture and air. Notably, it also exhibits excellent compatibility with various heterocyclic 1,3-dicarbonyls. The utility of this method has further been demonstrated by the late-stage functionalization of complex structures (e.g. styrylpyrone, simvastatin) and formal total synthesis of isocryptolepine.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"22 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127979","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 3,3-dialkyl-substituted isochroman-1,4-diones via copper/photoredox dual-catalyzed carbolactonization of alkenes 铜/光氧化还原双催化烯烃碳内化合成3,3-二烷基取代的异色-1,4-二酮
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-24 DOI: 10.1039/d5qo01082a
Pengfei Zhou, Ziyu Jin, Qiuping Ding, Jian-Qiang Chen, Jie Wu
{"title":"Synthesis of 3,3-dialkyl-substituted isochroman-1,4-diones via copper/photoredox dual-catalyzed carbolactonization of alkenes","authors":"Pengfei Zhou, Ziyu Jin, Qiuping Ding, Jian-Qiang Chen, Jie Wu","doi":"10.1039/d5qo01082a","DOIUrl":"https://doi.org/10.1039/d5qo01082a","url":null,"abstract":"We report a general and concise method for modular synthesis of various 3,3-dialkyl-substituted isochroman-1,4-diones via copper/photoredox dual-catalyzed carbolactonization of alkenoic acids with NHPI esters. A diverse range of NHPI esters derived from natural products and marketed drugs are successfully compatible with this reaction. With this approach, various alkyl-substituted isochroman-1,4-diones featuring a quaternary carbon center at the α-position of the carbonyl group can be synthesized in good to excellent yields.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"11 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127976","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Palladium-Catalyzed Endocyclic Bond Cleavage of Thioxanthene-derived Sulfonium Salts 钯催化的硫代蒽基磺酸盐的内环键断裂
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-24 DOI: 10.1039/d5qo00862j
yazhou lou, Chengfei Fu, Xing Chen, Junjie Zhao, Linglong Wan, Zhaoyu Sun, Xinhua Liu
{"title":"Palladium-Catalyzed Endocyclic Bond Cleavage of Thioxanthene-derived Sulfonium Salts","authors":"yazhou lou, Chengfei Fu, Xing Chen, Junjie Zhao, Linglong Wan, Zhaoyu Sun, Xinhua Liu","doi":"10.1039/d5qo00862j","DOIUrl":"https://doi.org/10.1039/d5qo00862j","url":null,"abstract":"The breaking of endocyclic S-aryl bond of strainless thioxanthene derivatives by transition metal-catalyzed ring-opening reactions are still underdeveloped. Herein, we presented the synthesis of unsymmetric triarylmethanes by desymmetric ring-opening reactions of strainless thioxanthene sulfonium salts with palladium-catalysis. The reaction exhibited broad substrate scopes, high efficiency and excellent chemoselectivity. Gram-scale experiments and asymmetric attempt for enantioselective and endocyclic bond-breaking reaction of the six-membered diarylthiolium salts was also investigated. Meanwhile, compound 3p showed comparatively good inhibition activities on NO generation in RAW264.7 cells through anti-inflammatory examination","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"76 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127972","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Overcoming Steric Constraints in C-H Arylation via Pd/Ag Dual Catalysis: A Shortcut to Ortho-Tetrasubstituted Heterobiaryl N-Oxides Pd/Ag双催化克服C-H芳基化的空间限制：一条邻四取代杂芳基n -氧化物的捷径
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-24 DOI: 10.1039/d5qo01137j
Peng Ye, Ya-Ling Zhang, ln xiong, Yang-Jie Mao, Yu-Qi Cui, Yong Luo, Dan-Qian Xu, Shao-Jie Lou
{"title":"Overcoming Steric Constraints in C-H Arylation via Pd/Ag Dual Catalysis: A Shortcut to Ortho-Tetrasubstituted Heterobiaryl N-Oxides","authors":"Peng Ye, Ya-Ling Zhang, ln xiong, Yang-Jie Mao, Yu-Qi Cui, Yong Luo, Dan-Qian Xu, Shao-Jie Lou","doi":"10.1039/d5qo01137j","DOIUrl":"https://doi.org/10.1039/d5qo01137j","url":null,"abstract":"The selective C-H arylation of <em>N</em>-containing aromatics with sterically demanding 2,6-disubstituted arylating reagents represents a straightforward way for the modular synthesis of <em>ortho</em>-tetra-substituted heterobiaryls, yet has remained scarcely explored due to the significant steric constraints and challenging selectivity control. Herein, we report a novel synergistic Pd-Ag catalysis system, which enables the regio-selective C-H arylation of different types of <em>N</em>-heterocyclic <em>N</em>-oxides with diverse <em>ortho</em>-disubstituted aryl iodides for the first time. This protocol offers a step-economic route for the synthesis of <em>ortho</em>-tetra-substituted heterobiaryl <em>N</em>-oxides, featuring novel catalytic mode, high regioselectivity, high yields, and broad substrate scope (45 examples, &gt;19:1 <em>r.r.</em> in most cases). The mechanistic details have been clarified by deuterium-labeling experiments, isolation and transformation of key intermediate, and DFT calculations, demonstrating the critical roles of Ag additive and DPEphos ligand for achieving high level of reactivity and regioselectivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"90 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127974","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 spiro-isoxazoline via a palladium-catalyzed carboetheri-fication of cycloalkenyl-tethered oximes 通过钯催化环烯基栓系肟的碳醚化反应获得螺-异恶唑啉
IF 5.4 1区 化学
Organic Chemistry Frontiers Pub Date : 2025-09-24 DOI: 10.1039/d5qo01162k
Qicai Ma, Yuanyuan Li, Zhiping Liu, Chengming Wang, Wei Zhou
{"title":"Access to spiro-isoxazoline via a palladium-catalyzed carboetheri-fication of cycloalkenyl-tethered oximes","authors":"Qicai Ma, Yuanyuan Li, Zhiping Liu, Chengming Wang, Wei Zhou","doi":"10.1039/d5qo01162k","DOIUrl":"https://doi.org/10.1039/d5qo01162k","url":null,"abstract":"This study presents an efficient method for synthesizing spiro-isoxazolines through a tandem palladium-catalyzed carboetherification approach. Utilizing cycloalkenyl-tethered oximes and aryl/alkenyl bromides, this protocol enables the construction of a wide range of novel spiro-isoxazoline compounds bearing diverse functional groups. Furthermore, we also investigated the asymmetric version of this tandem reaction, where the use of a chiral tert-butanesulfinamide monophosphine ligand achieved good chemical yield and excellent enantioselectivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"09 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-09-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145127973","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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