Asian Journal of Organic Chemistry最新文献

{"title":"Synthetic Strategies of Heterocycle‐Linked Sulfonamide Hybrids as Emerging Anticancer Agents: An Update","authors":"Sk Shamim Ahamed, Uma Sankar Mandal, Rahul Paul, Nilanjan Saha, Tapas Ghosh","doi":"10.1002/ajoc.70534","DOIUrl":"10.1002/ajoc.70534","url":null,"abstract":"<div><div>Sulfonamide‐containing heterocycles constitute a versatile and synthetically accessible class of scaffolds in contemporary anticancer drug discovery. In recent years, substantial progress has been made in developing efficient synthetic methodologies that enable the construction and late‐stage diversification of sulfonamide‐based hybrid architectures. This review provides a comprehensive overview of advances reported over the past five years in the synthesis of heterocycle‐integrated sulfonamide derivatives. Particular emphasis is placed on strategic bond‐forming approaches, modular scaffold assembly, and late‐stage sulfonylation protocols that facilitate structural diversification and rapid library generation. The discussion is organized according to the nature of the heterocyclic core, encompassing oxygen‐containing systems (e.g., coumarins, flavones, naphthoquinones, and oxadiazoles), nitrogen‐rich frameworks (including benzimidazoles, quinazolines, quinolines, triazines, and imidazole‐pyridine hybrids), nitrogen–sulfur fused scaffolds (such as benzothiazoles, thiadiazoles, and thienopyrimidines) and chalcone‐based sulfonamide hybrids, which represent an important class of molecularly hybridized anticancer scaffolds. Key synthetic strategies‐ranging from classical annulation methods and nucleophilic aromatic substitution to carbodiimide‐mediated coupling, Curtius rearrangement, click chemistry, and late‐stage <em>N</em>‐sulfonylation are critically analyzed with respect to efficiency, scope, and synthetic practicality. Collectively, these advances highlight the growing strategic importance of sulfonamide‐linked heterocyclic hybrids as promising platforms for anticancer drug development.</div></div><div>Sulfonamide‐containing heterocycles constitute a versatile and synthetically accessible class of scaffolds in contemporary anticancer drug discovery. In recent years, substantial progress has been made in developing efficient synthetic methodologies that enable the construction and late‐stage diversification of sulfonamide‐based hybrid architectures. This review provides a comprehensive overview of advances reported over the past five years in the synthesis of heterocycle‐integrated sulfonamide derivatives. Particular emphasis is placed on strategic bond‐forming approaches, modular scaffold assembly, and late‐stage sulfonylation protocols that facilitate structural diversification and rapid library generation. The discussion is organized according to the nature of the heterocyclic core, encompassing oxygen‐containing systems (e.g., coumarins, flavones, naphthoquinones, and oxadiazoles), nitrogen‐rich frameworks (including benzimidazoles, quinazolines, quinolines, triazines, and imidazole‐pyridine hybrids), nitrogen–sulfur fused scaffolds (such as benzothiazoles, thiadiazoles, and thienopyrimidines) and chalcone‐based sulfonamide hybrids, which represent an important class of molecularly hybridized anticancer scaffolds. Key synthetic str","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70534"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148860220","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Efficient Synthesis of Quinolines Through Acceptorless Dehydrogenative Coupling Enabled by an Air‐Stable Iridium(III) Pyrazolato Catalyst","authors":"Aditi Trivedi,&nbsp;Ratnakar Saha,&nbsp;Amrut Mohan Jena,&nbsp;Rasmiranjan Hota,&nbsp;Bidraha Bagh","doi":"10.1002/ajoc.70536","DOIUrl":"10.1002/ajoc.70536","url":null,"abstract":"<div><div>Quinoline derivatives were synthesized efficiently through acceptorless dehydrogenative coupling of amino alcohols or amino ketones with secondary alcohols using an air‐stable iridium(III) pyrazolato complex as catalyst. The protocol can operate under solvent‐free condition with catalyst loadings as low as 0.3 mol%, providing a broad range of quinoline frameworks in good to excellent yields. The methodology exhibits excellent functional‐group tolerance and utilizes readily accessible substrates, offering a practical route to structurally diverse quinoline derivatives. Importantly, water and molecular hydrogen are generated as the only byproducts, highlighting the sustainability and atom economy of the transformation. Mechanistic studies are consistent with a homogeneous, non‐radical pathway involving alcohol dehydrogenation as a key step, likely assisted by metal–ligand cooperation. The high catalytic efficiency, broad substrate scope and environmentally benign nature of this protocol make it an attractive strategy for the synthesis of valuable quinoline‐based heterocycles.</div></div><div>Quinoline derivatives were synthesized efficiently through acceptorless dehydrogenative coupling of amino alcohols or amino ketones with secondary alcohols using an air‐stable iridium(III) pyrazolato complex as catalyst. The protocol can operate under solvent‐free condition with catalyst loadings as low as 0.3 mol%, providing a broad range of quinoline frameworks in good to excellent yields. The methodology exhibits excellent functional‐group tolerance and utilizes readily accessible substrates, offering a practical route to structurally diverse quinoline derivatives. Importantly, water and molecular hydrogen are generated as the only byproducts, highlighting the sustainability and atom economy of the transformation. Mechanistic studies are consistent with a homogeneous, non‐radical pathway involving alcohol dehydrogenation as a key step, likely assisted by metal–ligand cooperation. The high catalytic efficiency, broad substrate scope and environmentally benign nature of this protocol make it an attractive strategy for the synthesis of valuable quinoline‐based heterocycles.</div><div>An air‐stable Cp*Ir(III)‐pyrazolato catalyst enables the efficient synthesis of quinolines through acceptorless dehydrogenative annulation of amino alcohols, amino ketones, secondary alcohols and ketones. Broad substrate scope, catalyst loadings as low as 0.3 mol% and generation of only H₂ and H₂O as byproducts highlight the practicality and sustainability of this metal–ligand cooperative catalytic process.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (48KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70536"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148942341","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Assessing the Efficiency of ortho‐Aminoaryl Carbonyls for Exploring Synthetic Diversity of Quinazolines: A Review","authors":"Minakshi G. Kalshetti,&nbsp;Pavankumar N. Nagtilak,&nbsp;Vijayalaxmi S. Swanne,&nbsp;Vikas D. Kadu","doi":"10.1002/ajoc.70537","DOIUrl":"10.1002/ajoc.70537","url":null,"abstract":"<div><div>Quinazoline‐based nitrogen heterocycles play vital role in medicinal chemistry due to their wide‐ranging biological activity and presence in several clinically relevant drugs and naturally occurring bioactive compounds. Beyond pharmaceuticals, quinazolines have applications in catalysis, materials science, sensing, supramolecular chemistry, and polymer science. Owing to their diverse adaptability, the significant advances have been made in the development of useful synthetic strategies for quinazolines, particularly <em>ortho</em>‐aminoaryl carbonyl compounds such as 2‐aminoaryl aldehydes and ketones. This review provides a comprehensive and integrated overview of these synthetic methods, reaction pathways, substrate scope, functional group tolerance, and operational limitations. Emphasis is placed on 2‐aminoaryl aldehydes/ketones precursors facilitating metal‐catalyzed, metal‐free, and heterogeneous and sustainable one‐pot synthesis for quinazoline synthesis. The review offers useful insights for the coherent designing of diverse quinazolines and highlights prospects for next‐generation heterocyclic scaffolds.</div></div><div>Quinazoline‐based nitrogen heterocycles play vital role in medicinal chemistry due to their wide‐ranging biological activity and presence in several clinically relevant drugs and naturally occurring bioactive compounds. Beyond pharmaceuticals, quinazolines have applications in catalysis, materials science, sensing, supramolecular chemistry, and polymer science. Owing to their diverse adaptability, the significant advances have been made in the development of useful synthetic strategies for quinazolines, particularly <em>ortho</em>‐aminoaryl carbonyl compounds such as 2‐aminoaryl aldehydes and ketones. This review provides a comprehensive and integrated overview of these synthetic methods, reaction pathways, substrate scope, functional group tolerance, and operational limitations. Emphasis is placed on 2‐aminoaryl aldehydes/ketones precursors facilitating metal‐catalyzed, metal‐free, and heterogeneous and sustainable one‐pot synthesis for quinazoline synthesis. The review offers useful insights for the coherent designing of diverse quinazolines and highlights prospects for next‐generation heterocyclic scaffolds.</div><div>Quinazoline‐based heterocycles are privileged scaffolds in biological and functional material applications. This review highlights advances in synthetic strategies from 2‐aminoaryl carbonyl precursors, emphasizing different approaches outlining mechanistic insights, scope, limitations, and future directions for designing diverse quinazolines.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (118KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70537"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148994191","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Cascade Annulation Enabled Access to Functionalized Polyaza Tetracycles With Fused Imidazo Scaffolds for Fluorescence “Turn‐Off” Sensing of Benzaldehyde Derivatives","authors":"Swarnali Ghosh,&nbsp;Saiful Islam,&nbsp;Anindita Sarkar,&nbsp;Tiyasa Ray,&nbsp;Kamalika Sen,&nbsp;Akhikesh Mahato,&nbsp;Anup Pramanik,&nbsp;Asish R Das","doi":"10.1002/ajoc.70530","DOIUrl":"10.1002/ajoc.70530","url":null,"abstract":"&lt;div&gt;&lt;div&gt;Regioselective Ru(II)‐catalyzed C(sp&lt;sup&gt;2&lt;/sup&gt;)─H activation with concomitant (4+2) cascade annulation materializes the benzimidazo‐ and imidazopyridine‐fused quinazolinyl ketones and quinazoline derivatives employing acyl azides and α‐azido ketones as the representative coupling surrogates. The insight of this protocol is established through control experiments and DFT analyses. Again, versatility is underscored by devising chemoselective imine bond reduction and directed nitro group functionalization ortho to the carbonyl moiety. In addition, bioactive ibuprofen‐appended benzimidazo‐quinazolinyl methanone analogue (&lt;strong&gt;3q&lt;/strong&gt;) and aspirin‐appended tetracyclic benzimidazo‐quinazoline analogue (&lt;strong&gt;5l&lt;/strong&gt;) have also been turned up, underscoring its potential significance as a novel pharmacologically relevant framework. Interestingly, a benzimidazo‐quinazoline derivative (&lt;strong&gt;5c&lt;/strong&gt;) showcased a pronounced fluorescence “turn‐off” response toward benzaldehyde and its substituted variant, with LODs of 2.03, 1.24, and 1.19 µM, respectively, exhibiting high sensitivity and selectivity.&lt;/div&gt;&lt;/div&gt;&lt;div&gt;Regioselective Ru(II)‐catalyzed C(sp&lt;sup&gt;2&lt;/sup&gt;)─H activation with concomitant (4+2) cascade annulation materializes the benzimidazo‐ and imidazopyridine‐fused quinazolinyl ketones and quinazoline derivatives employing acyl azides and α‐azido ketones as the representative coupling surrogates. The insight of this protocol is established through control experiments and DFT analyses. Again, versatility is underscored by devising chemoselective imine bond reduction and directed nitro group functionalization ortho to the carbonyl moiety. In addition, bioactive ibuprofen‐appended benzimidazo‐quinazolinyl methanone analogue (&lt;strong&gt;3q&lt;/strong&gt;) and aspirin‐appended tetracyclic benzimidazo‐quinazoline analogue (&lt;strong&gt;5l&lt;/strong&gt;) have also been turned up, underscoring its potential significance as a novel pharmacologically relevant framework. Interestingly, a benzimidazo‐quinazoline derivative (&lt;strong&gt;5c&lt;/strong&gt;) showcased a pronounced fluorescence “turn‐off” response toward benzaldehyde and its substituted variant, with LODs of 2.03, 1.24, and 1.19 µM, respectively, exhibiting high sensitivity and selectivity.&lt;/div&gt;&lt;div&gt;Regioselective Ru(II)‐catalyzed (sp&lt;sup&gt;2&lt;/sup&gt;)C─H activation associated with concomitant (4+2) cascade cyclization avenue leads to the efficient synthesis of benzimidazo‐ and imidazopyridine‐fused quinazolinyl ketones and quinazoline derivatives employing acyl azides and α‐azido ketones as the representative coupling partners to enrich the process. The reaction takes the course of C─H activation, nitrogen extrusion, annulation, and intramolecular cyclization under mild conditions. The process offers high regioselectivity, broad functional group tolerance, and the exclusive generation of benign nitrogen (gas) as the byproduct, averting the classical Curtius rearrangement. To further demonstrate the s","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70530"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148860219","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of Thioesters From Thioamides and Alkyl Halides With Water as the Oxygen Source and Solvent","authors":"Wenli Le,&nbsp;Jianchao Liu,&nbsp;Jie‐Ping Wan","doi":"10.1002/ajoc.70549","DOIUrl":"10.1002/ajoc.70549","url":null,"abstract":"<div><div>Thioesters are valuable compounds in both organic synthesis and pharmaceuticals. In this study, we report a practical, safe, and green approach for the rapid construction of thioesters from thioamides and alkyl halides without using any additive or catalyst. The synthetic reactions take place smoothly in water medium under air atmosphere to provide thioesters with broad scope and practical yield.</div></div><div>Thioesters are valuable compounds in both organic synthesis and pharmaceuticals. In this study, we report a practical, safe, and green approach for the rapid construction of thioesters from thioamides and alkyl halides without using any additive or catalyst. The synthetic reactions take place smoothly in water medium under air atmosphere to provide thioesters with broad scope and practical yield.</div><div>A practical and green approach for the rapid construction of thioesters from thioamides and alkyl halides has been reported. This transformation features readily available substrates, without need additives or catalysts and using environmentally benign water as both the solvent and oxygen source.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (18KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70549"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149047830","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Multicomponent Domino Approaches to the Persubstituted, Alkylene‐Bridged, and Hetero‐Fused CF3‐γ‐Lactams","authors":"Marina V. Goryaeva,&nbsp;Anna E. Ivanova,&nbsp;Yanina V. Burgart,&nbsp;Olesya A. Bakhareva,&nbsp;Marina A. Ezhikova,&nbsp;Mikhail I. Kodess,&nbsp;Pavel A. Slepukhin,&nbsp;Ksenia O. Malysheva,&nbsp;Olga P. Krasnykh,&nbsp;Aleksandrina S. Volobueva,&nbsp;Margarita A. Zinovieva,&nbsp;Mikhail G. Mikhalski,&nbsp;Victor I. Saloutin","doi":"10.1002/ajoc.70542","DOIUrl":"10.1002/ajoc.70542","url":null,"abstract":"<div><div>To synthesize persubstituted, alkylene‐bridged, and heterofused CF₃‐γ‐lactams, a domino strategy based on the multicomponent reaction of ethyl trifluoropyruvate and diethyl ketone with <em>N,N</em>‐ and <em>N,O</em>‐dinucleophilic reagents was developed. The structure of the final products depends on both the reaction conditions and the reagent ratio. It was found that bicyclic γ‐lactams and pyrrolidin‐2‐ones are predominantly formed under catalyst‐free conditions, whereas dual acid–base catalysis promotes the formation of <em>N</em>‐hydroxyalkyl‐substituted dihydropyrrol‐2‐ones and bis(dihydropyrrol‐2‐one) derivatives linked by an alkylene bridge. The diastereomeric structures of the newly synthesized CF₃‐γ‐lactams were established by ¹H, ¹⁹F, and ¹³C NMR spectroscopy, including two‐dimensional NMR experiments, as well as by x‐ray crystallographic analysis. A plausible mechanism for the multicomponent reaction is proposed and supported by additional synthetic experiments. Among the synthesized compounds, several derivatives exhibited analgesic and antiviral activities.</div></div><div>To synthesize persubstituted, alkylene‐bridged, and heterofused CF₃‐γ‐lactams, a domino strategy based on the multicomponent reaction of ethyl trifluoropyruvate and diethyl ketone with <em>N,N</em>‐ and <em>N,O</em>‐dinucleophilic reagents was developed. The structure of the final products depends on both the reaction conditions and the reagent ratio. It was found that bicyclic γ‐lactams and pyrrolidin‐2‐ones are predominantly formed under catalyst‐free conditions, whereas dual acid–base catalysis promotes the formation of <em>N</em>‐hydroxyalkyl‐substituted dihydropyrrol‐2‐ones and bis(dihydropyrrol‐2‐one) derivatives linked by an alkylene bridge. The diastereomeric structures of the newly synthesized CF₃‐γ‐lactams were established by ¹H, ¹⁹F, and ¹³C NMR spectroscopy, including two‐dimensional NMR experiments, as well as by x‐ray crystallographic analysis. A plausible mechanism for the multicomponent reaction is proposed and supported by additional synthetic experiments. Among the synthesized compounds, several derivatives exhibited analgesic and antiviral activities.</div><div>The multicomponent domino reaction of ethyl trifluoropyruvate and diethyl ketone with diamines/amino alcohols is an effective method for the synthesis of various CF₃‐γ‐lactams. Their structure varies depending on the dinucleophile and conditions. The pharmacological potential of new γ‐lactams is shown.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (75KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70542"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149047876","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Organocatalyzed Enantioselective Synthesis/Preparation of Chiral Maleimide‐Functionalized ɛ/δ‐Sultams via Mannich Reaction Between 3‐Arylaminomaleimides and Cyclic N‐Sulfonylimines","authors":"Hao‐Zhuang Zuo,&nbsp;Qian Li,&nbsp;Tao Wang,&nbsp;You‐Qing Wang","doi":"10.1002/ajoc.70550","DOIUrl":"10.1002/ajoc.70550","url":null,"abstract":"<div><div>A highly enantioselective Mannich reaction of 3‐arylaminomaleimides with seven/six‐membered cyclic <em>N</em>‐sulfonylimines has been disclosed. The reactions afforded a wide range of chiral maleimide‐modified <em>ɛ</em>/<em>δ</em>‐sultams in good yields (up to 99% yield) with excellent enantioselectivities (up to 99:1 <em>e.r</em>.) catalyzed by chiral <em>tert</em>‐amine organocatalysts. Scale‐up preparations of typical <em>ε</em>‐sultams were also performed with almost kept enantioselectivities and yields.</div></div><div>A highly enantioselective Mannich reaction of 3‐arylaminomaleimides with seven/six‐membered cyclic <em>N</em>‐sulfonylimines has been disclosed. The reactions afforded a wide range of chiral maleimide‐modified <em>ɛ</em>/<em>δ</em>‐sultams in good yields (up to 99% yield) with excellent enantioselectivities (up to 99:1 <em>e.r</em>.) catalyzed by chiral <em>tert</em>‐amine organocatalysts. Scale‐up preparations of typical <em>ε</em>‐sultams were also performed with almost kept enantioselectivities and yields.</div><div>A highly asymmetric Mannich reaction of 3‐arylaminomaleimides with seven/six‐membered cyclic <em>N</em>‐sulfonylimines to afford a wide range of chiral maleimide‐modified ɛ/δ‐sultams in good yields (up to 99% yield) and enantioselectivities (up to 99% ee) by utilizing organocatalysis with chiral amides has been established. \u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (66KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70550"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149048182","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Oxazolinyl‐Assisted Ru(II)‐Catalyzed Direct C─H Chalcogenation","authors":"Ran He,&nbsp;Chengcui Xiong,&nbsp;Xiaochun Cao,&nbsp;Yuchi Wang,&nbsp;Zheyu Li,&nbsp;Wenbo Ma,&nbsp;Linghui Gu","doi":"10.1002/ajoc.70538","DOIUrl":"10.1002/ajoc.70538","url":null,"abstract":"<div><div>The first oxazolinyl‐assisted ruthenium(II)‐catalyzed direct C─H chalcogenations of 2‐aryloxazolines has been achieved. The reaction proceeds smoothly with high functional group tolerance and regioselectivity to afford the sulfur‐ and selenium‐containing oxazoline compounds. The chalcogenation products can be easily converted into bioactive chalcogenoxanthones and useful sulfoxide‐oxazoline ligands. This efficient methodology is applied to the late‐stage modification of pharmaceutical compounds.</div></div><div>The first oxazolinyl‐assisted ruthenium(II)‐catalyzed direct C─H chalcogenations of 2‐aryloxazolines has been achieved. The reaction proceeds smoothly with high functional group tolerance and regioselectivity to afford the sulfur‐ and selenium‐containing oxazoline compounds. The chalcogenation products can be easily converted into bioactive chalcogenoxanthones and useful sulfoxide‐oxazoline ligands. This efficient methodology is applied to the late‐stage modification of pharmaceutical compounds.</div><div>Herein, we have developed the first ruthenium‐catalyzed direct C(sp²)‐H chalcogenation of 2‐aryloxazolines using a readily convertible oxazolinyl as the directing group. Notable features of our findings include (i) use of low‐cost ruthenium catalyst, (ii) high functional group tolerance and regioselectivity, (iii) readily transformable oxazoline directing group, (iv) compatibility with both diaryl and dialkyl diselenides, (v) easy access to biologically important chalcogenoxanthone derivatives and sulfoxide‐oxazoline ligands, (vi) applicability to the late‐stage diversification of pharmaceutical compounds.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (27KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 9","pages":"Article e70538"},"PeriodicalIF":2.3,"publicationDate":"2026-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148942866","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Silver‐Catalyzed [5+2] Cycloaddition of Terminal Alkynes With Imidazolidines: Access to 1,4‐Diazepines","authors":"Xia Zhang,&nbsp;Baoxin Zhang,&nbsp;Chao Pi,&nbsp;Yangjie Wu,&nbsp;Xiuling Cui","doi":"10.1002/ajoc.70502","DOIUrl":"10.1002/ajoc.70502","url":null,"abstract":"<div><div>Herein, we report a silver‐catalyzed [5+2] cycloaddition of terminal alkynes with imidazolidines, enabling the efficient synthesis of 1,4‐diazepines under mild conditions. The imidazolidine substrate acts as a novel 5‐atom synthon, undergoing silver‐mediated cyclization with terminal alkynes to deliver diverse 1,4‐diazepines in up to 92% yield with excellent functional group tolerance. This method provides a convenient route to access the privileged seven‐membered diazacyclic core, which is widely found in pharmaceuticals and bioactive molecules. Notably, the catalytic system is also applicable to the formal [6+2] cycloaddition of terminal alkynes with hexahydropyrimidines, allowing the construction of synthetically challenging eight‐membered diazacycles.</div></div><div>Herein, we report a silver‐catalyzed [5+2] cycloaddition of terminal alkynes with imidazolidines, enabling the efficient synthesis of 1,4‐diazepines under mild conditions. The imidazolidine substrate acts as a novel 5‐atom synthon, undergoing silver‐mediated cyclization with terminal alkynes to deliver diverse 1,4‐diazepines in up to 92% yield with excellent functional group tolerance. This method provides a convenient route to access the privileged seven‐membered diazacyclic core, which is widely found in pharmaceuticals and bioactive molecules. Notably, the catalytic system is also applicable to the formal [6+2] cycloaddition of terminal alkynes with hexahydropyrimidines, allowing the construction of synthetically challenging eight‐membered diazacycles.</div><div>In this work, we report a silver‐catalyzed [5+2]/[6+2] cycloaddition of terminal alkynes with imidazolidines and hexahydropyrimidines, enabling efficient access to diverse 1,4‐diazepines and eight‐membered diazacycles under mild conditions.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (17KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 8","pages":"Article e70502"},"PeriodicalIF":2.3,"publicationDate":"2026-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148647720","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A Unified Photoredox Platform for Divergent Dual C─H/N─H Selenylation to Access N,C‐ and C,C‐Diselenides","authors":"Fengxiang Zhu,&nbsp;Ying Hou,&nbsp;Xiao‐Feng Wu","doi":"10.1002/ajoc.70506","DOIUrl":"10.1002/ajoc.70506","url":null,"abstract":"<div><div>We report a visible‐light photoredox‐catalyzed strategy for the divergent dual selenylation of inert C─H and N─H bonds. Using a single catalytic system with Ru(bpy)₃Cl₂·6H₂O and diselenides, arylamines and indoles are selectively converted to distinct N,C‐ or C,C‐disubstituted organoselenides, respectively. This mild, redox‐neutral protocol features broad substrate scope, excellent regioselectivity, and operational simplicity, providing a unified and step‐economical route to valuable diselenides. Mechanistic studies support a radical‐based pathway.</div></div><div>We report a visible‐light photoredox‐catalyzed strategy for the divergent dual selenylation of inert C─H and N─H bonds. Using a single catalytic system with Ru(bpy)₃Cl₂·6H₂O and diselenides, arylamines and indoles are selectively converted to distinct N,C‐ or C,C‐disubstituted organoselenides, respectively. This mild, redox‐neutral protocol features broad substrate scope, excellent regioselectivity, and operational simplicity, providing a unified and step‐economical route to valuable diselenides. Mechanistic studies support a radical‐based pathway.</div><div>We report a visible‐light photoredox‐catalyzed strategy for the divergent dual selenylation of inert C─H and N─H bonds. Using a single catalytic system with Ru(bpy)₃Cl₂·6H₂O and diselenides, arylamines and indoles are selectively converted to distinct N,C‐ or C,C‐disubstituted organoselenides, respectively.\u0000<span><figure><span><img><ol><li><span><span>Download: <span>Download high-res image (23KB)</span></span></span></li><li><span><span>Download: <span>Download full-size image</span></span></span></li></ol></span></figure></span></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 8","pages":"Article e70506"},"PeriodicalIF":2.3,"publicationDate":"2026-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148752805","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}