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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
Synthesis, Antimicrobial and Antioxidant Activity with in silico ADMET Prediction, Molecular Docking and Dynamics Studies of Carbazole Ring Containing Thiazole Schiff Bases 含噻唑席夫碱的咔唑环的合成、抗菌和抗氧化活性，以及硅学 ADMET 预测、分子对接和动力学研究
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-05 DOI: 10.1002/ajoc.202400363
Sumita Saznin Marufa, Mohammad Mostafizur Rahman, Mizanur Rahman, Rownok Jahan, Gulshan Ara, Hiroshi Nishino, Mohammad Sayed Alam, Md. Aminul Haque
{"title":"Synthesis, Antimicrobial and Antioxidant Activity with in silico ADMET Prediction, Molecular Docking and Dynamics Studies of Carbazole Ring Containing Thiazole Schiff Bases","authors":"Sumita Saznin Marufa,&nbsp;Mohammad Mostafizur Rahman,&nbsp;Mizanur Rahman,&nbsp;Rownok Jahan,&nbsp;Gulshan Ara,&nbsp;Hiroshi Nishino,&nbsp;Mohammad Sayed Alam,&nbsp;Md. Aminul Haque","doi":"10.1002/ajoc.202400363","DOIUrl":"10.1002/ajoc.202400363","url":null,"abstract":"<p>Twelve thiazole hybrids (<b>2 a–2 l</b>) were synthesized in this study incorporating with Schiff base and carbazole scaffolds and characterized by spectral analyses. Antimicrobial activity and antioxidant potency were investigated by agar disc diffusion method and DPPH free radical scavenging assays where trimethyldihydrothiazole <b>2 c</b> had revealed its higher efficacy in both biological studies. It had displayed IC<sub>50</sub> of 25.55±0.40 μg/mL which is higher than the standard ascorbic acid (IC<sub>50</sub>=41.31±1.83 μg/mL) as well as dihydrothiazoylchromenone <b>2 e</b> showed promising antioxidant activity with IC<sub>50</sub> value of 40.82±0.54. The compound <b>2 c</b> satisfied all the ADME properties and toxicological parameters with maximum drug score value (0.39) among all derivatives. Molecular docking was undertaken for higher bioactive compounds where <b>2 c</b> revealed its wide range of interactions with different amino acid residues which was also endorsed with the output of molecular dynamics simulation.</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":"142217008","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
Catalytic Dearomative Cycloaddition Reactions Enabled by Visible Light 利用可见光进行催化Dearomative Cycloaddition反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-04 DOI: 10.1002/ajoc.202400374
Debajyoti Saha
{"title":"Catalytic Dearomative Cycloaddition Reactions Enabled by Visible Light","authors":"Debajyoti Saha","doi":"10.1002/ajoc.202400374","DOIUrl":"10.1002/ajoc.202400374","url":null,"abstract":"<p>The synthesis of polycyclic compounds is highly valued due to the ubiquitous presence of these structures in pharmaceuticals and natural substances. Cycloaddition reactions are notable as one of the most important reaction classes in chemical synthesis due to their ability to generate polycyclic compounds in a single step using straightforward and easily accessible starting materials. In recent times, visible-light-mediated photocatalysis has emerged as a powerful tool for enabling a wide range of transformations. Significant advancements have been achieved in dearomative cycloaddition reactions induced by visible light over the past several years. This review offers an overview of visible-light-induced dearomative cycloaddition reactions categorized according to the method of substrate excitation - a) Visible light induced dearomative photocatalytic cycloaddition by Energy Transfer (EnT); b) Visible light induced dearomative cycloaddition by direct excitation; c) Visible light induced dearomative radical cyclization.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217009","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
Dearomative Addition of Carboranyl Anions to Isoquinolinium Salts and Subsequent Reduction to Access Carborane-Functionalized 1,2-Dihydroisoquinolines and 1,2,3,4-Tetrahydroisoquinolines 硼烷阴离子与异喹啉鎓盐的亲和性加成及随后的还原反应，以获得硼烷官能化的二氢异喹啉
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-04 DOI: 10.1002/ajoc.202400390
Yun-Fan Gao, Chen-Ming Xu, Ming-Hui Yu, Yongna Zhang, Xiao-Jun Wu, You-Qing Wang
{"title":"Dearomative Addition of Carboranyl Anions to Isoquinolinium Salts and Subsequent Reduction to Access Carborane-Functionalized 1,2-Dihydroisoquinolines and 1,2,3,4-Tetrahydroisoquinolines","authors":"Yun-Fan Gao,&nbsp;Chen-Ming Xu,&nbsp;Ming-Hui Yu,&nbsp;Yongna Zhang,&nbsp;Xiao-Jun Wu,&nbsp;You-Qing Wang","doi":"10.1002/ajoc.202400390","DOIUrl":"10.1002/ajoc.202400390","url":null,"abstract":"<p>A dearomative addition of readily available carboranyllithium reagents to isoquinolinium salts gave a series of carborane cage C-substituted 1,2-dihydroisoquinolines in 43–85 % yields. Subsequent hydrogenation enabled the facile synthesis of corresponding carboranyl 1,2,3,4-tetrahydroisoquinolines in 65–95 % yields. The addition-reduction pathway is applicable to a wide range of substituted isoquinolinium salts and <i>o</i>-carborane or <i>m</i>-carborane.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217007","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
Thiol-Ene Coupling Reaction for Functionalization of Non-Activated Alkenes: An Experimental Study on the Chemistry of the Methyl Oleate Amination 用于非活性烯官能化的巯基-烯偶联反应：油酸甲酯胺化化学实验研究
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-03 DOI: 10.1002/ajoc.202400334
Mara L. Polo, David A. Echeverri, Laureana R. Soria, Victoria A. Vaillard, Gregorio R. Meira, Santiago E. Vaillard, Luis A. Ríos, Diana A. Estenoz
{"title":"Thiol-Ene Coupling Reaction for Functionalization of Non-Activated Alkenes: An Experimental Study on the Chemistry of the Methyl Oleate Amination","authors":"Mara L. Polo,&nbsp;David A. Echeverri,&nbsp;Laureana R. Soria,&nbsp;Victoria A. Vaillard,&nbsp;Gregorio R. Meira,&nbsp;Santiago E. Vaillard,&nbsp;Luis A. Ríos,&nbsp;Diana A. Estenoz","doi":"10.1002/ajoc.202400334","DOIUrl":"10.1002/ajoc.202400334","url":null,"abstract":"<p>This work investigates the functionalization of molecules with non-activated internal double bonds via thiol-ene coupling (TEC) reaction. A comprehensive study of the reaction between cysteamine hydrochloride (CAHC) and methyl oleate (MO) was carried out. A series of reactions were conducted under different operating conditions in order to assess their effect on conversion and selectivity. Different conditions were considered like the type of atmospheres and solvents, a portionwise addition of CAHC, reagents concentrations, and excess of CAHC. Maximum conversion and selectivity were reached under inert atmosphere, diluted conditions, ethanol as solvent, and the addition of CAHC at the beginning of the reaction with a molar ratio of CAHC/MO of 3/1. This provides an approach for analyzing more complex reaction systems.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217016","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 in Organocatalytic Enantioselective Reactions of α-Functionalized Propargylic Alcohols α官能化丙炔醇的有机催化对映体选择性反应的最新进展
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-03 DOI: 10.1002/ajoc.202400377
Yan Xia, Meiwen Liu, Wenjun Li, Pengfei Li
{"title":"Recent Advances in Organocatalytic Enantioselective Reactions of α-Functionalized Propargylic Alcohols","authors":"Yan Xia,&nbsp;Meiwen Liu,&nbsp;Wenjun Li,&nbsp;Pengfei Li","doi":"10.1002/ajoc.202400377","DOIUrl":"10.1002/ajoc.202400377","url":null,"abstract":"<p>Owing to their unique properties, propargylic alcohols have been recognized as one of the most attractive synthons in the field of organic synthesis. Particularly, with the aid of auxiliary group, the α-functionalized propargylic alcohols have been frequently involved in the organocatalytic enantioselective substitutions, conjugate additions, annulations and related reactions in recent years. Accordingly, the present review highlights recent advancements in the application of α-functionalized propargylic alcohols in the field of asymmetric organocatalysis, which is organized according to the type of auxiliary group.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217012","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
Gold Catalyzed [3+2] Oxidative Annulation of 1,3-Enynes with Indoles 金催化 1,3-炔与吲哚的 [3+2] 氧化环化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-02 DOI: 10.1002/ajoc.202400356
Qiang Zou, Yu-Jiang Wang, Ya-Ru Wan, Zili Chen
{"title":"Gold Catalyzed [3+2] Oxidative Annulation of 1,3-Enynes with Indoles","authors":"Qiang Zou,&nbsp;Yu-Jiang Wang,&nbsp;Ya-Ru Wan,&nbsp;Zili Chen","doi":"10.1002/ajoc.202400356","DOIUrl":"10.1002/ajoc.202400356","url":null,"abstract":"<p>An efficient new method has been developed for the synthesis of ketone-integrated cyclopentene-fused indoline derivatives with a high regioselectivity through gold-catalyzed oxidative cyclo-coupling of 1,3-enynes with indoles by using 2,6-dichloropyridine <i>N-o</i>xide as the terminal oxidant. A plausible mechanism has been proposed, in which, a cascade process of nucleophilic trapping of the vinyl gold carbene surrogate with indole followed by the subsequent intramolecular cyclization provides the dearomative formal [3+2] cycloaddition product. In addition, a scale-up reaction and further derivation via cyclopentene's epoxidation &amp; hydrazone derivative's 1,5- electrocyclization have been performed.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217013","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
Palladium Catalyzed Direct Ortho C-H Acylation of 4-Phenylquinazoline Using Methylarenes as Acylation Reagents 钯催化的以甲基烯为酰化试剂的 4-苯基喹啉直接正交 C-H 酰化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-02 DOI: 10.1002/ajoc.202400394
Tongtong Deng, Shan Hu, Xianyu Ying, Hui Wang, Prof. Hongjun Zhu
{"title":"Palladium Catalyzed Direct Ortho C-H Acylation of 4-Phenylquinazoline Using Methylarenes as Acylation Reagents","authors":"Tongtong Deng,&nbsp;Shan Hu,&nbsp;Xianyu Ying,&nbsp;Hui Wang,&nbsp;Prof. Hongjun Zhu","doi":"10.1002/ajoc.202400394","DOIUrl":"10.1002/ajoc.202400394","url":null,"abstract":"<p>A simple ortho-acylation of 4-phenylquinazoline by a Pd-catalyzed oxidative C−H activation was developed, with moderate yields, in which no prefunctionalized methylarenes were used as acylation reagents. Moreover, this methodology tolerates a wide range of functional groups. Radical scavenging experiments indicate that the acylation involves a benzoyl radical pathway.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217010","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
Base Induced Synthesis of Isochroman Spiropyrazolones Via Bifunctional Peroxides 通过双官能团过氧化物在碱诱导下合成异铬螺吡唑酮类化合物
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-02 DOI: 10.1002/ajoc.202400438
Jiaxu Feng, Xiangdi Wang, Yingying Wu
{"title":"Base Induced Synthesis of Isochroman Spiropyrazolones Via Bifunctional Peroxides","authors":"Jiaxu Feng,&nbsp;Xiangdi Wang,&nbsp;Yingying Wu","doi":"10.1002/ajoc.202400438","DOIUrl":"10.1002/ajoc.202400438","url":null,"abstract":"<p>Isochroman is one of the powerful scaffolds which demonstrated various important biologically activities. Herein we represented the novel and versatile method for the synthesis of valuable isochroman spiropyrazolones of difunctional peroxides and pyrazolones via [1+5] annulation. This process represents a novel spiroisochroman synthesis protocol and is featured by good functional group compatibility, mild conditions and readily available substrates.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217011","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
Photo-Induced Sulfonylation/Trifluoromethylation-Peroxidation of Alkenes via EnT-Mediated N−S Bond Homolysis of N-Sulfonyl Ketimines 通过 EnT 介导的 N-磺酰基酮亚胺的 N-S 键同解，实现光诱导的磺酰化/三氟甲基化-烯烃过氧化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-02 DOI: 10.1002/ajoc.202400384
Yuting Feng, Leiyang Lv, Zhiping Li
{"title":"Photo-Induced Sulfonylation/Trifluoromethylation-Peroxidation of Alkenes via EnT-Mediated N−S Bond Homolysis of N-Sulfonyl Ketimines","authors":"Yuting Feng,&nbsp;Leiyang Lv,&nbsp;Zhiping Li","doi":"10.1002/ajoc.202400384","DOIUrl":"10.1002/ajoc.202400384","url":null,"abstract":"<p>Photocatalytic sulfonylation/trifluoromethylation-peroxidation of alkenes with <i>N</i>-sulfonyl ketimines and <i>tert</i>-butyl hydroperoxide is reported. The transformation is initiated by the EnT-driven homolytic S−<i>N</i> bond cleavage of <i>N</i>-sulfonyl ketimines. The sulfonyl-peroxides were obtained when alkyl sulfonyl radicals were captured by alkene via sequential C−S and C−O bond formation, while a thermodynamically favored release of SO<sub>2</sub> from trifluoromethane sulfonyl radical generated CF<sub>3</sub> radical and afforded the trifluoromethyl-peroxides.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 12","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217015","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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