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Sustainable Synthesis of D-Glucose Based IL: A Renewable Organo Catalyst for the Efficient Synthesis of Dihydropyrano Coumarins 可持续合成 D-葡萄糖基 IL：高效合成二氢吡喃香豆素的可再生有机催化剂
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-14 DOI: 10.1002/ajoc.202400202
Krishnaraj P, Treesa Mary Chacko, Sathi Bhulakshmi, Chun-Cheng Lin, Prof. Dr. Sabbasani Rajasekhara Reddy
{"title":"Sustainable Synthesis of D-Glucose Based IL: A Renewable Organo Catalyst for the Efficient Synthesis of Dihydropyrano Coumarins","authors":"Krishnaraj P,&nbsp;Treesa Mary Chacko,&nbsp;Sathi Bhulakshmi,&nbsp;Chun-Cheng Lin,&nbsp;Prof. Dr. Sabbasani Rajasekhara Reddy","doi":"10.1002/ajoc.202400202","DOIUrl":"10.1002/ajoc.202400202","url":null,"abstract":"<p>A convenient, direct, one-pot highly efficient microwave-assisted synthesis of biomass-derived D-glucose-based hydroxide ionic liquid <i>via</i> a simple three-step approach has been described. The key features of the method include rapidness, eco-friendliness, and excellent yields. To the best of our knowledge, this is the first methodology for synthesizing D-Glucose-based sugar ionic liquid (GSIL) under microwave irradiation. The developed catalyst allowed us to synthesize diverse dihydropyrano[3,2-c]-chromenes upto 95 % yield in 30-90 min stirring at 80 °C under mild conditions. The scope of the study was investigated using 30 instances. Developed GSIL exhibited excellent catalytic activity as well as good recyclability. Overall, the catalyst showed excellent value in green chemistry parameters such as atom economy (95 %), E-factor (0.05), carbon efficiency (100 %), process mass intensity (1.62), and reaction mass efficiency (0.860).</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142253009","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}
引用次数: 0
Front Cover: Rapidly Diverse Synthesis of N-Aryl-5-Substituted-2-Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates (Asian J. Org. Chem. 9/2024) 封面：通过亲核环氧开环和分子内酰基取代环氧氨基甲酸酯快速合成N-芳基-5-取代的-2-恶唑烷酮 (Asian J. Org. Chem. 9/2024)
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-13 DOI: 10.1002/ajoc.202480901
Nian-Xuan Lin, Shih-Ming Chang, Xin-Shun Chiou, Kelly Lee, Yu-Tung Tsai, Prof. Dr. Cheng-Kun Lin
{"title":"Front Cover: Rapidly Diverse Synthesis of N-Aryl-5-Substituted-2-Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates (Asian J. Org. Chem. 9/2024)","authors":"Nian-Xuan Lin,&nbsp;Shih-Ming Chang,&nbsp;Xin-Shun Chiou,&nbsp;Kelly Lee,&nbsp;Yu-Tung Tsai,&nbsp;Prof. Dr. Cheng-Kun Lin","doi":"10.1002/ajoc.202480901","DOIUrl":"https://doi.org/10.1002/ajoc.202480901","url":null,"abstract":"<p>In article number e202400188, Cheng-Kun Lin and co-workers present a method to convert epoxy carbamates to oxazolidinones by combining intermolecular nucleophilic epoxide ring opening with intramolecular acyl substitution in a single step, enabling rapid conversion. It demonstrates favourable reactivity across various aryl groups, benzyl, or tert-butyl carbamates, consistently yielding satisfactory results, with oxazolidinone formation ranging from 55% to 99% across over 24 examples.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 9","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202480901","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142233196","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Microwave-Assisted One-Pot Synthesis of Tetrahydro-β-Carbolines by Fe(II)-Catalyst: Utilizing Methanol as Methylene Synthon 铁(II)催化剂微波辅助一锅合成四氢-β-羰基化合物：利用甲醇作为亚甲基合成物
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-12 DOI: 10.1002/ajoc.202400404
Mursalim A. Khan, Rajkumar Reddyrajula, Akash P. Sakla, Manda Sathish, Nagula Shankaraiah
{"title":"Microwave-Assisted One-Pot Synthesis of Tetrahydro-β-Carbolines by Fe(II)-Catalyst: Utilizing Methanol as Methylene Synthon","authors":"Mursalim A. Khan,&nbsp;Rajkumar Reddyrajula,&nbsp;Akash P. Sakla,&nbsp;Manda Sathish,&nbsp;Nagula Shankaraiah","doi":"10.1002/ajoc.202400404","DOIUrl":"10.1002/ajoc.202400404","url":null,"abstract":"<p>The synthesis of tetrahydro-β-carbolines (THβCs) framework is a fundamental aspect of medicinal chemistry due to their significant pharmacological applications. Herein, we developed a microwave-assisted novel approach for the synthesis of THβC scaffolds utilizing ferrous(II) chloride as an earth abundant metal catalyst and methanol used as valuable methylene source. This methodology demonstrates excellent functional group tolerance and provides <i>N</i>2-substituted THβCs in good to excellent yields. Overall, this study highlights a sustainable and practical strategy for the synthesis of biologically important THβCs, thereby offering promising prospects in the drug discovery and development.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216971","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}
引用次数: 0
Kinetic Resolution of α-Allyl-α-Cinnamyl Carboxylic Acids Bearing an All-Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide 通过手性双官能团硫化物催化的溴化内酯化作用，动力学解析带有全碳季立体中心的 α-烯丙基-α-肉桂酰基羧酸
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-11 DOI: 10.1002/ajoc.202400405
Ken Okuno, Sao Sumida, Seiji Shirakawa
{"title":"Kinetic Resolution of α-Allyl-α-Cinnamyl Carboxylic Acids Bearing an All-Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide","authors":"Ken Okuno,&nbsp;Sao Sumida,&nbsp;Seiji Shirakawa","doi":"10.1002/ajoc.202400405","DOIUrl":"10.1002/ajoc.202400405","url":null,"abstract":"<p>Catalytic kinetic resolutions of racemic carboxylic acids are important methods for preparing chiral carboxylic acids in their optically active forms. While several effective methods for the catalytic kinetic resolution of chiral α-tertiary carboxylic acids have been reported, the efficient kinetic resolution of α-quaternary carboxylic acids remains a significant challenge. In this context, we aimed to develop methods for the kinetic resolution of α-quaternary carboxylic acids. Our approach involves a BINOL-derived chiral bifunctional sulfide-catalyzed bromolactonization technique, which was developed by our research group. In this work, we report the kinetic resolution of α-allyl-α-cinnamyl carboxylic acids bearing an α-quaternary stereocenter via chemo- and stereoselective bromolactonizations. The use of a BINOL-derived chiral bifunctional sulfide catalyst with a hydroxy group was key for the efficient kinetic resolution of racemic α-allyl-α-cinnamyl carboxylic acids.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217077","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}
引用次数: 0
Synthesis and Evaluations of Cleavable Triazene-Modified Nucleotide for DNA Sequencing 用于 DNA 测序的可裂解三嗪修饰核苷酸的合成与评估
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-11 DOI: 10.1002/ajoc.202400393
Pingyang Wang, Bowei Tang, Yumei Shen
{"title":"Synthesis and Evaluations of Cleavable Triazene-Modified Nucleotide for DNA Sequencing","authors":"Pingyang Wang,&nbsp;Bowei Tang,&nbsp;Yumei Shen","doi":"10.1002/ajoc.202400393","DOIUrl":"10.1002/ajoc.202400393","url":null,"abstract":"<p>A fluorescence-labeled nucleotide with a cleavable triazene linker was designed and synthesized as a potential reversible terminator for DNA sequencing by synthesis (SBS). The key intermediate, a triazene-modified nucleotide, was successfully synthesized through the triazenylation of an amino-modified nucleotide, followed by fluorescence labeling to yield the desired product. The synthesized triazene-modified nucleotide can effectively serve as a substrate for Klenow Fragment (exo−) DNA polymerase and be incorporated into DNA strands. Once the first modified nucleotide is incorporated, no further extension is possible, even with an unblocked 3′-OH group. After the fluorescent label is completely removed under acidic conditions, the triazene reversible terminator can be incorporated into DNA strands again, thereby enabling the DNA sequencing cycles.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216967","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}
引用次数: 0
Synthesis of Naphthalenones Via Photo-Induced Radical Cascade Fluoroalkylation/Cyclization of Alkenes 通过烯烃的光诱导自由基级联氟烷基化/环化合成萘酮
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-11 DOI: 10.1002/ajoc.202400354
Xiaohu Yang, Chunmei Yang, Xiaoqing Wan, Wenchao Yang, Hegui Fang
{"title":"Synthesis of Naphthalenones Via Photo-Induced Radical Cascade Fluoroalkylation/Cyclization of Alkenes","authors":"Xiaohu Yang,&nbsp;Chunmei Yang,&nbsp;Xiaoqing Wan,&nbsp;Wenchao Yang,&nbsp;Hegui Fang","doi":"10.1002/ajoc.202400354","DOIUrl":"10.1002/ajoc.202400354","url":null,"abstract":"<p>Herein, we report a photoredox-catalyzed fluoroalkylation of activated alkenes via fluorinated alkyl-centered radical induced radical addition/annulation/SET/deprotonation in a domino fashion using 4CzIPN as photocatalyst. The protocol features room temperature, transition metal free, high yields and simple operation, affording a facile and efficient strategy to access fluorine-containing naphthalenone.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216969","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}
引用次数: 0
TMSOTf-Catalyzed Annulation of Ynamides with Alkynyl Sulfoxides to Construct Substituted Maleimides TMSOTf 催化亚酰胺与炔基硫醚的环化反应，构建取代的马来酰亚胺类化合物
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-08 DOI: 10.1002/ajoc.202400416
Nanfang Wang, Wozheng Fang, Yu Yan, Nan Sun, Junbiao Chang, Xiao-Na Wang
{"title":"TMSOTf-Catalyzed Annulation of Ynamides with Alkynyl Sulfoxides to Construct Substituted Maleimides","authors":"Nanfang Wang,&nbsp;Wozheng Fang,&nbsp;Yu Yan,&nbsp;Nan Sun,&nbsp;Junbiao Chang,&nbsp;Xiao-Na Wang","doi":"10.1002/ajoc.202400416","DOIUrl":"10.1002/ajoc.202400416","url":null,"abstract":"<p>A TMSOTf-catalyzed annulation was developed for the construction of polysubstituted maleimides from ynamides and alkynyl sulfoxides, using oxygen as a green oxidant and ynamides as both carbon and nitrogen sources. This novel protocol proceeds in the presence of TMSOTf without the need for an expensive catalytic system and tolerates a broad substrate scope, providing a variety of maleimides in generally moderate to good yields under mild reaction conditions.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216972","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}
引用次数: 0
Recent Advances on Regioselective C−H Borylation of Indoles 吲哚的区域选择性 C-H Borylation 的最新进展
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-08 DOI: 10.1002/ajoc.202400464
Dr. Yanyan Guo, Meiyu Wang, Prof. Dr. Guodu Liu
{"title":"Recent Advances on Regioselective C−H Borylation of Indoles","authors":"Dr. Yanyan Guo,&nbsp;Meiyu Wang,&nbsp;Prof. Dr. Guodu Liu","doi":"10.1002/ajoc.202400464","DOIUrl":"10.1002/ajoc.202400464","url":null,"abstract":"<p>Borylated indoles are versatile building blocks for functional molecules, such as pharmaceutical and natural products. However, the C−H borylation regioselectivity of unprotected indoles with seven distinct sites has been a problem for a long time. Among the various synthetic approaches to borylated indoles, transition-metal-catalyzed, electrophilic C−H borylation and chelation effect directed C−H borylation are attractive methods because of their powerful ability to rapidly construct various C−H borylation of indoles. In this review, we highlight the developments in the C−H borylation regioselectivity of indole using these methods of C−H borylation over the last 20 years. With a focus on the mechanism of the C−H borylation of indole, further studies and developments of this field would be inspired in the future.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216968","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}
引用次数: 0
Solvent-Free Dehydrogenative C−H Chalcogenations of Pyrazolones Using Mechanochemistry 利用机械化学法实现吡唑酮的无溶剂脱氢 C-H Chalcogenation
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-06 DOI: 10.1002/ajoc.202400353
Tao Zheng, Zihan Yu, Junlong Li, Qilin Gu, Linghui Gu, Zheyu Li, Wenbo Ma
{"title":"Solvent-Free Dehydrogenative C−H Chalcogenations of Pyrazolones Using Mechanochemistry","authors":"Tao Zheng,&nbsp;Zihan Yu,&nbsp;Junlong Li,&nbsp;Qilin Gu,&nbsp;Linghui Gu,&nbsp;Zheyu Li,&nbsp;Wenbo Ma","doi":"10.1002/ajoc.202400353","DOIUrl":"10.1002/ajoc.202400353","url":null,"abstract":"<p>A mechanochemical cross-dehydrogenative coupling reaction of pyrazolones with thiols using ball milling is described. Benzeneselenol and dichalcogenide substrates are also compatible under mild reaction conditions, yielding up to 99 %. Notable features of this reaction include its metal- and solvent-free, wide substrate scope and good functional group tolerance. Preliminary mechanistic investigations suggest that a radical pathway is likely involved in this C−H chalcogenation reaction.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216970","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}
引用次数: 0
Metal-Free Generation of Acyl Fluorides via Activation of Cyclopropyl Esters using a Hypervalent Iodine(III) Species and Selectfluor 使用高价碘（III）物种和 Selectfluor 通过活化环丙基酯无金属生成酰基氟化物。
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-05 DOI: 10.1002/ajoc.202400398
Eun-Sol Choi, Hyo-Jun Lee, Keiji Maruoka
{"title":"Metal-Free Generation of Acyl Fluorides via Activation of Cyclopropyl Esters using a Hypervalent Iodine(III) Species and Selectfluor","authors":"Eun-Sol Choi,&nbsp;Hyo-Jun Lee,&nbsp;Keiji Maruoka","doi":"10.1002/ajoc.202400398","DOIUrl":"10.1002/ajoc.202400398","url":null,"abstract":"<p>An efficient method for the activation of non-activated cyclopropyl esters is developed using a hypervalent iodine(III) species and Selectfluor for the generation of acyl fluoride intermediates. The reactive acyl fluoride intermediate is smoothly transformed into various functional groups such as amides, esters, thioesters, and ketones depending on the nucleophile used in the in-situ transformation. Utilizing the oxidation process of an iodoarene by Selectfluor, the activation is improved from a stoichiometric to catalytic protocol. Furthermore, the activation is employed in the chemoselective activation of target cyclopropyl ester in the presence of other ester moieties.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217006","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}
引用次数: 0
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