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First Total Synthesis of Inaoside A
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”
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
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
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
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
NHC-Catalyzed [3+3] Cycloaddition of 2-(acetoxymethyl)buta-2,3-dienoates with 1 C,3O-bisnucleophiles
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
Divergent Sc(OTf)3-Catalyzed Tandem Cyclization of o-Hydroxyphenyl Enaminones with 1,3,5-Triazinanes: Access to C3-Aminomethyl Chromones and Tetrahydropyrimidines
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
Site-Selective Synthetic Modifications of the Cinchona Alkaloids
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
Substituent Controlled Tunable Fluorescence from Green to Red and pH Stimuli‐Induced Reversible Fluorescence Switching in Triphenylamine–Quinoxaline Derivatives 三苯胺-喹喔啉衍生物中由取代基控制的从绿到红的可调荧光和 pH 值刺激诱导的可逆荧光转换
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400282
Jerome Issac , Sasikala Ravi , Subrmanian Karthikeyan , Govindasami Periyasami , Dohyun Moon , Savarimuthu Philip Anthony , Vedichi Madhu
{"title":"Substituent Controlled Tunable Fluorescence from Green to Red and pH Stimuli‐Induced Reversible Fluorescence Switching in Triphenylamine–Quinoxaline Derivatives","authors":"Jerome Issac ,&nbsp;Sasikala Ravi ,&nbsp;Subrmanian Karthikeyan ,&nbsp;Govindasami Periyasami ,&nbsp;Dohyun Moon ,&nbsp;Savarimuthu Philip Anthony ,&nbsp;Vedichi Madhu","doi":"10.1002/ajoc.202400282","DOIUrl":"10.1002/ajoc.202400282","url":null,"abstract":"<div><div>A series of triphenylamine‐quinoxaline donor‐acceptor (bipolar) compounds (<strong>TPA‐QH</strong>, <strong>TPA‐QMe</strong>, <strong>TPA‐QCOOH</strong> and <strong>TPA‐QNO<sub>2</sub></strong>) with different substituents were synthesized and investigated their fluorescence properties, including stimuli‐induced fluorescence responses in solution and the solid‐state. Single crystal structural analysis revealed non‐planar molecular conformation, substituent controlled intermolecular interactions and molecular packing in the crystal lattice. <strong>TPA‐QH</strong>, <strong>TPA‐QMe</strong>, <strong>TPA‐QCOOH</strong> and <strong>TPA‐QNO<sub>2</sub></strong> showed tunable solid‐state emission from green to red. <strong>TPA‐QH</strong> showed strong fluorescence at 487 nm (quantum yield (Φ<sub>f</sub>)=28.3 %) whereas NO<sub>2</sub> substituted <strong>TPA‐QNO<sub>2</sub></strong> exhibited relatively weak fluorescence at 610 nm (Φ<sub>f</sub>=4.3 %). Density functional theoretical (DFT) calculations also indicated reduction of optical bandgap with substituting electron withdrawing group. The donor‐acceptor structure with intramolecular charge transfer (ICT) resulted solvent polarity dependent fluorescence tuning. The presence of acid responsive quinoxaline group was utilized to demonstrate pH‐responsive fluorescence switching and dual state fluorescence was utilized for fabricating rewritable fluorescent platform. Thus, the present study provides a structural insight to develop dual state emissive triphenylamine–quinoxaline based bipolar materials for optoelectronic applications.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400282"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141872248","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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