Xuan Zhang , Ge Jin , Qin Zhang , Chaoyue Sun , Yun Han , Changbin Dou , Zhaoyi Yuan , Lingyu Xia , Shu Yun , Dr. Mianran Chao , Dr. Duyi Shen
{"title":"Flavoenzyme‐inspired Reductive Dehalogenation of α‐Br and α‐Cl Carbonyl Compounds with Riboflavin Tetraacetate as Photocatalyst","authors":"Xuan Zhang , Ge Jin , Qin Zhang , Chaoyue Sun , Yun Han , Changbin Dou , Zhaoyi Yuan , Lingyu Xia , Shu Yun , Dr. Mianran Chao , Dr. Duyi Shen","doi":"10.1002/ajoc.202400709","DOIUrl":"10.1002/ajoc.202400709","url":null,"abstract":"<div><div>Reductive dehalogenation represented a straightforward way to the breakage of carbon‐halogen bonds, exerting great significance in organic synthesis and potential in environmental decontamination. Riboflavin, a small molecular, photosensitive, and redox‐responsible coenzyme in both oxidases and reductase, has inspired various biological and biomimetic photocatalytic oxidations but a few biocatalytic reductions. Herein, we described a visible‐light‐induced reduction of C−Br and C−Cl bonds to form C−H bonds using riboflavin tetraacetate (RFT) as a flavoenzyme‐inspired photocatalyst. The halogen atoms of α‐bromo‐ and α‐chloro carbonyl compounds could be smoothly removed at room temperature with triethanolamine as a suitable terminal reductant and a sustainable solvent system consisting of ethanol and water. A series of deuterium isotope labeling experiments indicated that the hydrogen atom sources of the dehalogenated products should be water, reductant, and the hydroxyl group rather than the α‐hydrogen atom of the alcoholic solvent. Other control experiment and UV‐Vis studies suggested the single electron transfer process between the excited photocatalyst and the reductant, the reduced photocatalyst and the C−X bond, respectively. This work further tapped the versatile capacities of riboflavin‐based photocatalysts in chemical reductions more than conventional oxidative reactions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400709"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846054","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}
Chunping Dong , Yue Zhang , Caijuan Hu , Yongsheng Zhou , Jian Li
{"title":"Iodine‐Catalyzed Aerobic Oxidative Domino Cyclization of Methyl N‐Heteroarenes with 6‐Aminopyrimidine‐2,4‐Dione and Pyrazol‐5‐Amine","authors":"Chunping Dong , Yue Zhang , Caijuan Hu , Yongsheng Zhou , Jian Li","doi":"10.1002/ajoc.202400714","DOIUrl":"10.1002/ajoc.202400714","url":null,"abstract":"<div><div>An iodine‐catalyzed aerobic oxidative domino annulation of methyl <em>N</em>‐heteroarenes with 6‐aminopyrimidine‐2,4‐dione and pyrazol‐5‐amine has been developed for the synthesis of dipyrimidine/dipyrazolo‐fused pyridines using 1,3‐dibromobenzene as the additive and oxygen as the terminal oxidant. Detailed mechanistic studies indicated that 1,3‐dibromobenzene enhanced the solubility of O<sub>2</sub>, and facilitated the aerobic oxidation of I<sup>−</sup> to I<sub>2</sub>, thereby promoting the aerobic oxidative domino cyclization reaction. The gram scale reaction was also successful using this methodology.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400714"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846063","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":"2‐oxo‐2H‐chromen‐7‐olate Catalyzed C−C and C−N Bond Formations in Visible Light","authors":"Vikas Dixit , Shruti Sharma , Nidhi Jain","doi":"10.1002/ajoc.202400684","DOIUrl":"10.1002/ajoc.202400684","url":null,"abstract":"<div><div>7‐hydroxycoumarin is a naturally occurring compound with useful biological and fluorescent properties. In this work, we demonstrate a base‐assisted photoactivation of 7‐hydroxycoumarin in blue LED and its potential in enabling C−C and C−N bond formations. 7‐hydroxycoumarin, on deprotonation with Cs<sub>2</sub>CO<sub>3</sub> forms 2‐oxo‐2<em>H</em>‐chromen‐7‐olate which exhibits photoreductant properties and mediates arylation and hydroxyarylation using hypervalent iodonium ylides; alkylation using <em>N</em>‐hydroxyphthalimide esters; and amination with primary and secondary amines. The strategy does not require any additional metal or organic dye‐based photocatalyst and offers a good functional group tolerance giving the C−C and C−N coupled products in moderate to good yields.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400684"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846088","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}
Himani Karakoti , Ravendra Kumar , Pooja Bargali , Sonu Kumar Mahawer , Srutee Rout , Suraj N. Mali , Mozaniel Santana de Oliveira
{"title":"A Comprehensive Insight into the Phytochemistry, Pharmacology, and Therapeutic Potential of Digitalis purpurea L.","authors":"Himani Karakoti , Ravendra Kumar , Pooja Bargali , Sonu Kumar Mahawer , Srutee Rout , Suraj N. Mali , Mozaniel Santana de Oliveira","doi":"10.1002/ajoc.202400657","DOIUrl":"10.1002/ajoc.202400657","url":null,"abstract":"<div><div><em>Digitalis purpurea</em> L., commonly referred to as foxglove, is a biennial herbaceous plant indigenous to Western and Central Europe and has become widely established in temperate areas across the globe. Renowned for its vibrant bell‐shaped flowers, <em>D. purpurea</em> has a long‐standing history of medicinal use, particularly for treating cardiovascular issues. The plant is abundant in secondary metabolites, such as cardiac glycosides, flavonoids, phenolic compounds, and alkaloids, which contribute to its significant pharmacological effects. Among these, the cardiac glycosides digoxin and digitoxin are notable active compounds extensively used in managing conditions like congestive heart failure and atrial fibrillation. In addition to its cardiotonic properties, <em>D. purpurea</em> is recognized for its anti‐inflammatory, antioxidant, anticancer, neuroprotective, and antimicrobial effects, generating increasing interest in contemporary medicine. This review examines the mechanisms through which these bioactive compounds operate, addresses safety considerations and potential toxicities related to <em>D. purpurea</em> use, and highlights current research trends. By emphasizing the necessity for careful administration and monitoring due to its narrow therapeutic window, this paper aims to underscore the therapeutic potential and future opportunities for <em>D. purpurea</em> in treating various diseases.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400657"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846085","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":"PdII-Catalyzed γ-C(sp3)–H (Hetero)Arylation of Ketones Using Acetohydrazide As The Transient Directing Group","authors":"Kai Jia, Jun Luo, Chao Jiang","doi":"10.1002/ajoc.202500289","DOIUrl":"https://doi.org/10.1002/ajoc.202500289","url":null,"abstract":"<p>Pd(II)-catalyzed <i>γ</i>-C(sp<sup>3</sup>)–H (hetero)arylation of aliphatic ketones is developed using acetohydrazide as the transient directing group (TDG). The reaction is facilitated by a crucial 2-pyridone ligand via the 5,6-membered fused palladacycle intermediate, enabling the smooth <i>γ</i>-C(sp<sup>3</sup>)–H (hetero)arylation of various aliphatic ketones. The reaction demonstrated tolerance to different functional groups of aryl iodides, and compatibility with various pyridinyl or quinolinyl iodides. Furthermore, regioselectivity of <i>γ</i>-C(sp<sup>3</sup>)–H arylation with current reaction conditions was compared with previous studies for the challenging substrate pentan-2-one.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 6","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291802","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":"Asymmetric Synthesis of Chiral Sulfimides","authors":"Saori Tsuzuki , Taichi Kano","doi":"10.1002/ajoc.202400765","DOIUrl":"10.1002/ajoc.202400765","url":null,"abstract":"<div><div>Chiral sulfimides (sulfilimines), aza‐analogues of sulfoxides, are valuable compounds in organic synthesis and medicinal chemistry. They show unique biological properties, and the stereochemistry of the sulfur atom affects their biological activity. This mini‐review highlights the development in asymmetric synthesis of chiral sulfimides over the last hundred years.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400765"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845797","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}
Suhasini Mohapatra , Sonali Priyadarshini Parida , Dr. Sabita Nayak , Kabita Behera , Seetaram Mohapatra
{"title":"Aqueous‐Mediated Microwave Synthesis of Novel Tetrahydrospiro [Chromeno‐Isoxazole‐Indolinone] Derivatives via 1,3‐Dipolar Cycloaddition Reaction","authors":"Suhasini Mohapatra , Sonali Priyadarshini Parida , Dr. Sabita Nayak , Kabita Behera , Seetaram Mohapatra","doi":"10.1002/ajoc.202500029","DOIUrl":"10.1002/ajoc.202500029","url":null,"abstract":"<div><div>A regiospecific approach has been developed for the synthesis of 2,2‐disubstituted 2‐phenyl‐2,3<em>a</em>,4,9<em>b</em>‐tetrahydrospiro[chromeno[4,3‐<em>d</em>]isoxazole‐1,3’‐indolin]‐2’‐one derivatives <em>via</em> 1,3‐dipolar cycloddition reaction. This one‐pot, two‐component synthesis involves 2<em>H</em>‐chromene and <em>N</em>‐arylisatin nitrones in aqueous medium, promoting a green synthesis by minimizing the use of hazardous reagents and enhancing the sustainability of synthesis. The cycloadducts, which feature a spiro center, are efficiently obtained under both conventional method and microwave irradiation. The newly developed derivatives were characterized using <sup>1</sup>H, <sup>13</sup>C NMR, as well as HRMS spectra. Furthermore, the structure of compound <strong>16 a</strong> was unambiguously confirmed through single‐crystal X‐ray analysis.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202500029"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143845879","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":"Unusual Electrophilic Reactivity of Sulfonyl Phthalide in Its Microwave‐Mediated One‐Pot Transformation to Novel Oxime Phthalides","authors":"Rajni Kumari , Dr. Irishi N. N. Namboothiri","doi":"10.1002/ajoc.202400814","DOIUrl":"10.1002/ajoc.202400814","url":null,"abstract":"<div><div>A microwave‐assisted nucleophilic substitution of sulfonyl group in 3‐sulfonyl phthalide is reported for the first time. In contrast to its normal nucleophilic reactivity under basic conditions, sulfonyl phthalide acts as a mono‐electrophile with oxime affording oxime phthalides in good to excellent yields and good functional group tolerance. Scalability of the reaction and further transformation of oxime phthalide to tribromo‐methylated phthalide and phthalazinone have been demonstrated.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400814"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846048","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}
Nestor‐F. Bravo , Carlos Cifuentes , Maria‐C. Ríos , Lady‐J. Pérez , Prof. Jaime Portilla
{"title":"Synthesis and Photophysical Properties of Conjugated Fluorophores with N‐Heteroaromatic Rings","authors":"Nestor‐F. Bravo , Carlos Cifuentes , Maria‐C. Ríos , Lady‐J. Pérez , Prof. Jaime Portilla","doi":"10.1002/ajoc.202400742","DOIUrl":"10.1002/ajoc.202400742","url":null,"abstract":"<div><div>Fluorescent molecules are vital parts of modern chemistry and find widespread use in our daily lives, being potent tools for quantitatively and qualitatively determining analytes in many habitats, including living systems. Their exceptional properties allow us to visualize and understand complex biological processes, even beyond intracellular levels, advancing our knowledge of life; they also play a focal role in materials science and the environment. All these facts highlight these compounds′ impact in all sciences despite several restricted uses since many dyes have poor synthetic viability and biocompatibility with limited optical and electronic properties. These flaws could be solved by conjugating a representative fluorophore with an N‐heteroaromatic moiety, which has proven helpful in this target. Thus, this review aims to analyze advances from the years 2019 to 2023 in syntheses and photophysical properties of N‐heteroaromatic compounds conjugated with (i) triphenylamine (TPA), (ii) coumarin (CM), (iii) boron complexes (BC), or (iv) aromatic hydrocarbons (AHs).</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 4","pages":"Article e202400742"},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143846102","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}
Muhammad Ehtisham Ibraheem Khan, Lu Wang, Dr. Benedetta Bassetti, Prof. Dr. Marino Petrini, Prof. Dr. Alessandro Palmieri
{"title":"SnX2 Promoted Cyclization of β-Nitro-β,γ-unsaturated Ketones Into 3-(2-Haloalkyl)-5-aryl Isoxazoles","authors":"Muhammad Ehtisham Ibraheem Khan, Lu Wang, Dr. Benedetta Bassetti, Prof. Dr. Marino Petrini, Prof. Dr. Alessandro Palmieri","doi":"10.1002/ajoc.202500076","DOIUrl":"https://doi.org/10.1002/ajoc.202500076","url":null,"abstract":"<p>Herein we report an easy and fruitful methods to synthesize 3-(2-haloalkyl)-5-aryl isoxazoles starting from <i>β</i>-nitro-β,γ-unsaturated ketones. The reaction was promoted by the presence of tin (II) chloride or bromide and products were obtained in good yields and in short reaction time. Moreover, we extended our methodology to flow chemical conditions, and we also tested the usefulness of halogenated isoxazoles to obtain amino and ether derivatives.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 6","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291804","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}