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Asian Journal of Organic Chemistry最新文献

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Silane‐Mediated Alkylation of Arenes via Reductive Friedel‐Crafts Reaction Using Carbonyl Compounds 硅烷通过羰基化合物的还原 Friedel-Crafts 反应介导的烯烃烷基化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-11-01 DOI: 10.1002/ajoc.202400347
Jabir Khan , Rina Mahato , Kanhaiya , Chinmoy Kumar Hazra
{"title":"Silane‐Mediated Alkylation of Arenes via Reductive Friedel‐Crafts Reaction Using Carbonyl Compounds","authors":"Jabir Khan ,&nbsp;Rina Mahato ,&nbsp;Kanhaiya ,&nbsp;Chinmoy Kumar Hazra","doi":"10.1002/ajoc.202400347","DOIUrl":"10.1002/ajoc.202400347","url":null,"abstract":"<div><div>A metal‐free one‐pot synthesis route has been documented for the production of 1,1‐unsymmetrical di‐aryl alkanes <em>via</em> reductive Friedel−Crafts alkylation of arenes with carbonyl compounds in 1,1,1,3,3,3,–hexafluoroisopropanol (HFIP) solvent. This approach exhibits a wide substrate scope accommodating diverse functionalities. The transformation of carbonyl compounds into alkylated products is facilitated by dimethylchlorosilane (Me<sub>2</sub>SiClH) reduction, succeeded <em>via</em> nucleophilic attack of arenes. The established protocol demonstrates a promising strategy for converting indoline‐2,3‐dione into <em>α</em>‐aryl oxindoles with high yields. The reaction involves reduction with Me<sub>2</sub>SiClH, followed by the attack of arenes in the presence of a TfOH catalyst. The devised protocol offers scalability and remarkable tolerance towards various functional groups. Control experiments provide insights into the reaction mechanism, highlighting the crucial roles of HFIP and Me<sub>2</sub>SiClH. Furthermore, the method is adaptable for late‐stage functionalization of numerous natural products and pharmaceuticals such as Sesamol, Thymol, Paracetamol, Menthol, and Nerol. Significantly, the technique has proven effective in efficiently synthesising the anticoagulant drug Phenprocoumon and the rodent control agent Coumatetralyl.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":"Article e202400347"},"PeriodicalIF":2.8,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217025","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
First Total Synthesis of Inaoside A 稻葵苷A的首次全合成
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-31 DOI: 10.1002/ajoc.202400547
Tomoya Takao, Atsushi Kawamura, Hidefumi Makabe
{"title":"First Total Synthesis of Inaoside A","authors":"Tomoya Takao,&nbsp;Atsushi Kawamura,&nbsp;Hidefumi Makabe","doi":"10.1002/ajoc.202400547","DOIUrl":"https://doi.org/10.1002/ajoc.202400547","url":null,"abstract":"<p>The first total synthesis of inaoside A, an α-<span>d</span>-ribofuranoside isolated by our group from the edible mushroom <i>Laetiporus cremeiporus</i>, is described. The key reaction was an α-selective Schmidt glycosylation. Most reported syntheses of ribofuranosides following the general Schmidt glycosylation procedure preferentially give β-ribofuranosides. In contrast, using a 2,3,5-tri-<i>O</i>-(<i>tert</i>-butyldimethylsilyl)-protected ribofuranoside substrate, which is easy to prepare and can be deprotected after glycosylation, revealed that the α-ribofuranoside was preferentially obtained.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862422","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: Direct In Situ Polymer Modification of Titania Nanomaterial Surfaces via UV-irradiated Radical Polymerization (Asian J. Org. Chem. 10/2024) 封面：通过紫外辐射辐射聚合对钛纳米材料表面进行直接原位聚合物改性（亚洲有机化学杂志 10/2024）
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-15 DOI: 10.1002/ajoc.202481001
Tomonari Tanaka, Shota Nishimura, Kaito Nishiyama, Yuji Aso, Hisataka Nishida, Sunghun Cho, Tohru Sekino
{"title":"Front Cover: Direct In Situ Polymer Modification of Titania Nanomaterial Surfaces via UV-irradiated Radical Polymerization (Asian J. Org. Chem. 10/2024)","authors":"Tomonari Tanaka,&nbsp;Shota Nishimura,&nbsp;Kaito Nishiyama,&nbsp;Yuji Aso,&nbsp;Hisataka Nishida,&nbsp;Sunghun Cho,&nbsp;Tohru Sekino","doi":"10.1002/ajoc.202481001","DOIUrl":"https://doi.org/10.1002/ajoc.202481001","url":null,"abstract":"<p>This cover highlights direct polymer modification of titania nanotube (TNT) surfaces via UV-irradiated radical polymerization and is drawn in a manga style. Vinyl monomers were reacted by UV-irradiated radical polymerization using titania nanotubes. The direct in situ polymer modification of TNTs was achieved without pretreatment of titania. The resulting polymer-modified TNTs retain the original photocatalytic properties. More details can be found in article number e202400270 by Tomonari Tanaka and co-workers.<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 10","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202481001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142435484","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
“Novel Metal-Free Porphyrin with Ionic Liquid and Sulphonic Acid Moieties for Visible Light Assisted Photocatalytic C−N Coupling of Heterocyclic Compounds with Aryl Halides” "具有离子液体和磺酸分子的新型无金属卟啉，用于可见光辅助的杂环化合物与芳基卤化物的 C-N 光催化偶联反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-14 DOI: 10.1002/ajoc.202400337
Piyush Radheshyam Yadav, Pundlik Rambhau Bhagat
{"title":"“Novel Metal-Free Porphyrin with Ionic Liquid and Sulphonic Acid Moieties for Visible Light Assisted Photocatalytic C−N Coupling of Heterocyclic Compounds with Aryl Halides”","authors":"Piyush Radheshyam Yadav,&nbsp;Pundlik Rambhau Bhagat","doi":"10.1002/ajoc.202400337","DOIUrl":"https://doi.org/10.1002/ajoc.202400337","url":null,"abstract":"<p>Metal-free Buchwald-Hartwig type photocatalytic approach for N-substitution of 1,2,4-triazole at normal temperature was explored for the first-time using novel imidazolium based Brønsted acid functionalized porphyrin (ImBAFPc). The energy band gap and Hammett acidity were determined by UV-Vis spectrophotometer. The energy band gap, 1.06 eV supported absorption of radiation in the visible region. The N-arylation of 1,2,4-triazole with various Ar−X was achieved in a home-made photoreactor by heterogeneous, recyclable ImBAFPc photocatalyst under irradiation of 5 W LED with good yields. The protocol tolerated electron donating and attracting Ar−X, including inactivated chlorobenzene, affording the arylated triazole with admirable yields. under ambient photocatalytic conditions.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142861275","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
Multicomponent Cyanation of 2-Amino-3-cyano-4H-chromenes in Aqueous Media 水溶液中2-氨基-3-氰基- 4h -铬的多组分氰化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-09 DOI: 10.1002/ajoc.202400443
Sandra Ardevines, Miryam Garcés-Marín, Paula Cervantes-Cerrada, Subhan AAmir, Raquel P. Herrera, Eugenia Marqués-López
{"title":"Multicomponent Cyanation of 2-Amino-3-cyano-4H-chromenes in Aqueous Media","authors":"Sandra Ardevines,&nbsp;Miryam Garcés-Marín,&nbsp;Paula Cervantes-Cerrada,&nbsp;Subhan AAmir,&nbsp;Raquel P. Herrera,&nbsp;Eugenia Marqués-López","doi":"10.1002/ajoc.202400443","DOIUrl":"https://doi.org/10.1002/ajoc.202400443","url":null,"abstract":"<p>Chromenes represent a pivotal molecular structure found in a diverse range of biologically active compounds. Specifically, derivatives of 2-amino-3-cyano-4<i>H</i>-chromene have demonstrated pharmacological applications, displaying potential antioxidant and anticancer activities. This has heightened interest in the exploration of new and more efficient methods for their synthesis. In recent years, few examples have emerged, focusing on the organocatalytic and enantioselective synthesis of 2-amino-3-cyano-4<i>H</i>-chromene derivatives, although the overall number of works to date is limited. In this study, we present the results of the synthesis of 2-amino-4<i>H</i>-chromen-3,4-dicarbonitriles through a Michael addition of cyanide to 2-iminochromenes. To achieve this, we utilized a mild source of cyanide (acetone cyanohydrin), green solvents and catalytic conditions at room temperature, <i>via</i> a multicomponent approach. Furthermore, we initiated the enantioselective study of this process using chiral organocatalysts obtaining promising preliminary results.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400443","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860552","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
Conjugate Addition of 3-Aryl Oxindoles to In Situ Generated o–Quinone Methides Without Essential Electronic or Steric Groups 3 芳基羰基吲哚与原位生成的邻喹酮甲酰胺的共轭加成，不含基本电子或立体基团
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-08 DOI: 10.1002/ajoc.202400370
Liu Song
{"title":"Conjugate Addition of 3-Aryl Oxindoles to In Situ Generated o–Quinone Methides Without Essential Electronic or Steric Groups","authors":"Liu Song","doi":"10.1002/ajoc.202400370","DOIUrl":"https://doi.org/10.1002/ajoc.202400370","url":null,"abstract":"<p>Herein an efficient method for <i>in situ</i> generated <i>o</i>–quinone methides without essential electronic or steric groups at the exocyclic methylene or on six-membered ring was established. The method relies on acetylation of salicylylols and subsequently base promoted 1,4-elimination. The <i>in situ</i> generated <i>o</i>–quinone methides could be undergoing conjugate addition with 3-aryl oxindoles in one-pot reaction system, which provided 3,3-disubstituted oxindoles bearing a quaternary stereocenter in good yields (up to 99 %).</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860748","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
Utilization of Lipase-Catalyzed Acetylation and Deacetylation in the Synthesis of a Natural Product with a Hydroquinone Skeleton 脂肪酶催化乙酰化和去乙酰化在合成对苯二酚骨架天然产物中的应用
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-08 DOI: 10.1002/ajoc.202400303
Takeshi Sugai, Keiko Honda, Riichi Hashimoto, Kengo Hanaya, Shuhei Higashibayashi
{"title":"Utilization of Lipase-Catalyzed Acetylation and Deacetylation in the Synthesis of a Natural Product with a Hydroquinone Skeleton","authors":"Takeshi Sugai,&nbsp;Keiko Honda,&nbsp;Riichi Hashimoto,&nbsp;Kengo Hanaya,&nbsp;Shuhei Higashibayashi","doi":"10.1002/ajoc.202400303","DOIUrl":"https://doi.org/10.1002/ajoc.202400303","url":null,"abstract":"<p>Elaborated conditions for lipase-catalyzed preferential monoacetylation enabled the large-scale preparation of hydroquinone monoacetate. This product was then applied to the synthesis of tournefolin B, a highly oxygenated prenylated hydroquinone of plant origin (<i>Tournefortia sarmentosa</i> Lam.). During the course of the synthetic transformations, lipase-catalyzed deacetylation under mild conditions was demonstrated.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860747","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
Divergent Sc(OTf)3-Catalyzed Tandem Cyclization of o-Hydroxyphenyl Enaminones with 1,3,5-Triazinanes: Access to C3-Aminomethyl Chromones and Tetrahydropyrimidines 发散Sc(OTf)3催化邻羟基苯基胺酮与1,3,5-三嗪烷的串联环化：c3 -氨基甲基色酮和四氢嘧啶的获得
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-08 DOI: 10.1002/ajoc.202400391
Siyang Han, Chengcheng Fang, Sifeng Li, Xiaoye Mo, Yingqian Xu, Baigang An, Bin Cheng
{"title":"Divergent Sc(OTf)3-Catalyzed Tandem Cyclization of o-Hydroxyphenyl Enaminones with 1,3,5-Triazinanes: Access to C3-Aminomethyl Chromones and Tetrahydropyrimidines","authors":"Siyang Han,&nbsp;Chengcheng Fang,&nbsp;Sifeng Li,&nbsp;Xiaoye Mo,&nbsp;Yingqian Xu,&nbsp;Baigang An,&nbsp;Bin Cheng","doi":"10.1002/ajoc.202400391","DOIUrl":"https://doi.org/10.1002/ajoc.202400391","url":null,"abstract":"<p>A Sc(OTf)<sub>3</sub>-catalyzed tandem cyclization reaction of <i>o</i>-hydroxyphenyl enaminones with 1,3,5-triazinanes has been developed to generate two distinct annulated products in moderate to good yields, which is dominated by the electronic characteristics of the 1,3,5-triazinanes. The 1,3,5-triaryl-1,3,5-triazinane reacted as C−N synthon to produce C3-aminomethyl chromone, while the 1,3,5-trialkyl-1,3,5-triazinane acted as C−N−C−N synthons to deliver <i>N</i>,<i>N</i>-dialkyl tetrahydropyrimidine with a free hydroxyl group.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860749","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
NHC-Catalyzed [3+3] Cycloaddition of 2-(acetoxymethyl)buta-2,3-dienoates with 1 C,3O-bisnucleophiles nhc催化的2-（乙酰氧基甲基）丁酸-2,3-二烯酸酯与1,30 -双亲核试剂的[3+3]环加成反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-08 DOI: 10.1002/ajoc.202400439
Wei Cao, Kai Zhang, Chenxia Yu, Changsheng Yao
{"title":"NHC-Catalyzed [3+3] Cycloaddition of 2-(acetoxymethyl)buta-2,3-dienoates with 1 C,3O-bisnucleophiles","authors":"Wei Cao,&nbsp;Kai Zhang,&nbsp;Chenxia Yu,&nbsp;Changsheng Yao","doi":"10.1002/ajoc.202400439","DOIUrl":"https://doi.org/10.1002/ajoc.202400439","url":null,"abstract":"<p>Diverse transformations of allenoates catalyzed by Lewis bases have emerged as a powerful platform for generating new chemical entities in organic synthesis. Herein, an <i>N</i>-heterocyclic carbene (NHC) catalyzed [3+3] cyclization of 2-(acetoxymethyl)buta-2,3-dienoates with 1 C,3O-bisnucleophiles has been developed. This approach provides a facile method to synthesize highly functionalized 4<i>H</i>-pyran derivatives with a broad substrate scope (31 examples, up to 83 % yield).</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860746","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
Site-Selective Synthetic Modifications of the Cinchona Alkaloids 金鸡纳生物碱的位点选择性合成修饰
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-07 DOI: 10.1002/ajoc.202400397
Finlay P. Player, Daniel J. Foley
{"title":"Site-Selective Synthetic Modifications of the Cinchona Alkaloids","authors":"Finlay P. Player,&nbsp;Daniel J. Foley","doi":"10.1002/ajoc.202400397","DOIUrl":"https://doi.org/10.1002/ajoc.202400397","url":null,"abstract":"<p>The natural product quinine has been known to humankind for centuries, and in that time has played a pivotal role in the treatment of malaria. Quinine, and the related cinchona alkaloids, have seen widespread contemporary use across chemical and biological disciplines, owing in part to the plethora of functional groups and stereochemical information contained within their scaffold. This review focuses on site-selective synthetic modifications of the cinchona alkaloids. Our comparative analysis may act as a ‘user manual’ for the selective functionalisation of the cinchona alkaloids, and aims to promote consideration of remarkable and lesser-understood aspects of cinchona chemistry.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142860655","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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