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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 2.7 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 Soria, Victoria A. Vaillard, Gregorio Meira, Santiago E. Vaillard, Luis A. Ríos, Diana 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, David A. Echeverri, Laureana Soria, Victoria A. Vaillard, Gregorio Meira, Santiago E. Vaillard, Luis A. Ríos, Diana Estenoz","doi":"10.1002/ajoc.202400334","DOIUrl":"https://doi.org/10.1002/ajoc.202400334","url":null,"abstract":"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..","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":2.7,"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
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 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-03 DOI: 10.1002/ajoc.202400438
jiaxu feng, Xiangdi Wang, Yingying Wu
{"title":"Base induced synthesis of isochroman spiropyrazolones via bifunctional peroxides","authors":"jiaxu feng, Xiangdi Wang, Yingying Wu","doi":"10.1002/ajoc.202400438","DOIUrl":"https://doi.org/10.1002/ajoc.202400438","url":null,"abstract":"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 spiroisocchroman synthesis protocol and is featured by good functional group compatibility, mild conditions and readily available substrates.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"74 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-03","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
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 2.7 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, Meiwen Liu, Wenjun Li, Pengfei Li","doi":"10.1002/ajoc.202400377","DOIUrl":"https://doi.org/10.1002/ajoc.202400377","url":null,"abstract":"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.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.7,"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
HBr/TMSO/HFIP Mediated Chemoselective Modifications of Pyrrolo[2,1-a]Isoquinolines HBr/TMSO/HFIP 介导的吡咯并[2,1-a]异喹啉化合选择性修饰
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-02 DOI: 10.1002/ajoc.202400323
Yun-Meng Li, Man Jiang, Jing Zhou, Prof. Dr. Hai-Lei Cui
{"title":"HBr/TMSO/HFIP Mediated Chemoselective Modifications of Pyrrolo[2,1-a]Isoquinolines","authors":"Yun-Meng Li,&nbsp;Man Jiang,&nbsp;Jing Zhou,&nbsp;Prof. Dr. Hai-Lei Cui","doi":"10.1002/ajoc.202400323","DOIUrl":"10.1002/ajoc.202400323","url":null,"abstract":"<p>The combination of HBr, TMSO (tetramethylene sulfoxide) and HFIP (hexafluoroisopropanol) has been utilized in the modification of pyrrolo[2,1-<i>a</i>]isoquinoline derivatives through bromination, dimerization and sulfenylation respectively. In these processes, HBr serves as the source of bromine and TMSO acts as an oxidant. HFIP also plays an essential role for the oxidative dimerization. Chemoselectivity can be easily controlled by adjusting the parameters such as reaction time, ratio of reagents and the addition of nucleophile.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217014","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 2.7 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, Leiyang Lv, Zhiping Li","doi":"10.1002/ajoc.202400384","DOIUrl":"https://doi.org/10.1002/ajoc.202400384","url":null,"abstract":"Photocatalytic sulfonylation/trifluoromethylation‐peroxidation of alkenes with N‐sulfonyl ketimines and tert‐butyl hydroperoxide is reported. The transformation is initiated by the EnT‐driven homolytic S‐N bond cleavage of N‐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 SO2 from trifluoromethane sulfonyl radical generated CF3 radical and afforded the trifluoromethyl‐peroxides.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"52 1","pages":""},"PeriodicalIF":2.7,"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
Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS-CoV-2 Spike Glycoprotein and Influenza A Virus 抗 SARS-CoV-2 穗状糖蛋白和甲型流感病毒的新型阿比坦类糖三唑混合物和酰胺类化合物
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-01 DOI: 10.1002/ajoc.202400227
Dr. Elena Tretyakova, Dr. Liwen Hua, Anna Smirnova, Prof. Dr. Oxana Kazakova, Prof. Dr. Vladimir Zarubaev, Dr. Hongwei Jin, Dr. Huan Xu, Prof. Dr. Sulong Xiao
{"title":"Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS-CoV-2 Spike Glycoprotein and Influenza A Virus","authors":"Dr. Elena Tretyakova,&nbsp;Dr. Liwen Hua,&nbsp;Anna Smirnova,&nbsp;Prof. Dr. Oxana Kazakova,&nbsp;Prof. Dr. Vladimir Zarubaev,&nbsp;Dr. Hongwei Jin,&nbsp;Dr. Huan Xu,&nbsp;Prof. Dr. Sulong Xiao","doi":"10.1002/ajoc.202400227","DOIUrl":"10.1002/ajoc.202400227","url":null,"abstract":"<p>Abietane type diterpenic (dehydroabietic, 2,3-dihydroquinopimaric and maleopimaric) acids were converted by the acid chloride method into a series of aliphatic and heterocyclic amine spacered conjugates. A number of structurally novel derivatives holding 1,2,3-triazole moieties were designed and synthesized by treating of the propargylated amides and esters with a sugar azides using the Cu(I)-catalyzed click chemistry approach. The synthesized <i>N</i>-containing diterpene derivatives were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in MDCK cell culture and SARS-CoV-2 pseudovirus in BHK-21-hACE2 cells. Among tested forty-five compounds ten derivatives were the most efficacious against influenza virus A with IC<sub>50</sub> 0.7–63.4 μM together with high selectivity index SI value from 11 from 94. Dihydroquinopimaric acid <i>N</i>-ethylpiperazine-amide and dehydroabietic acid 1,2,3-triazoles spacered with glucose and lactose showed anti-SARS-CoV-2 pseudovirus activity with EC<sub>50</sub> values of 1.79–25.46 μM. Molecular docking and dynamics modeling investigated the binding mode of the lead compounds into the binding pocket of influenza A virus M2 protein and the RBD domain of SARS-CoV-2 spike glycoprotein.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227007","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
Facile and Metal-Free Synthesis of Isoflavones Using α-Aryl-β,β-Ditosyloxy Ketones 用 α-芳香族酮类化合物合成 ISOFLAVONES 的无毡和无金属结构物
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-29 DOI: 10.1002/ajoc.202400336
Omkar Bains, Ashish Kumar, Raj Kamal, Ravinder Kumar, Rajesh Kumar, Tanmay Rom, Avijit Kumar Paul
{"title":"Facile and Metal-Free Synthesis of Isoflavones Using α-Aryl-β,β-Ditosyloxy Ketones","authors":"Omkar Bains,&nbsp;Ashish Kumar,&nbsp;Raj Kamal,&nbsp;Ravinder Kumar,&nbsp;Rajesh Kumar,&nbsp;Tanmay Rom,&nbsp;Avijit Kumar Paul","doi":"10.1002/ajoc.202400336","DOIUrl":"10.1002/ajoc.202400336","url":null,"abstract":"<p>Considering the drawbacks associated with available synthetic methodologies of isoflavones, herein we have reported a metal-free and eco-friendly approach to these natural products. In the present study, we have carried out the synthesis of eight isoflavone derivatives <b>7a</b>–<b>7h</b> using α-aryl-β,β-ditosyloxy ketone protocol. Initially, we have protected the 2’-hydroxy group of respective chalcone moiety in order to remove its interference under reaction conditions. The protected chalcones were then subjected to 1,2-aryl migration by being treated with hydroxy(tosyloxy)iodobenzene (HTIB) reagent in a non-nucleophilic solvent (CH<sub>2</sub>Cl<sub>2</sub>). This migration furnished the formation of α-aryl-β,β-ditosyloxy ketones via C−C bond formation from their corresponding chalcones in moderate to good yields (55–82 %). The ambiguity regarding the exact molecular structure of the α-aryl-β,β-ditosyloxy ketones was examined through the single crystal X-ray diffraction data. At last, the synthesis of isoflavones was carried out in moderate to good yields (50–80 %) by performing the reaction of α-aryl-β,β-ditosyloxy ketones with sodium hydroxide in aqueous methanol.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217017","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 Pyrrolidine-fused β-lactams as Potential β-lactamase Inhibitors 合成吡咯烷融合的β-内酰胺作为潜在的β-内酰胺酶抑制剂
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-28 DOI: 10.1002/ajoc.202400364
Dr. Sari Deketelaere, Dr. Carlos Díez-Poza, Margot Aelbrecht, Jonas Mortier, Bram Van Den Bossche, Dr. Jorick Franceus, Prof. Dr. Tom Desmet, Prof. Dr. Kristof Van Hecke, Prof. Dr. Christian V. Stevens, Prof. Dr. Matthias D'hooghe
{"title":"Synthesis of Pyrrolidine-fused β-lactams as Potential β-lactamase Inhibitors","authors":"Dr. Sari Deketelaere,&nbsp;Dr. Carlos Díez-Poza,&nbsp;Margot Aelbrecht,&nbsp;Jonas Mortier,&nbsp;Bram Van Den Bossche,&nbsp;Dr. Jorick Franceus,&nbsp;Prof. Dr. Tom Desmet,&nbsp;Prof. Dr. Kristof Van Hecke,&nbsp;Prof. Dr. Christian V. Stevens,&nbsp;Prof. Dr. Matthias D'hooghe","doi":"10.1002/ajoc.202400364","DOIUrl":"10.1002/ajoc.202400364","url":null,"abstract":"<p>A synthetic protocol for the preparation of novel 3,4-pyrrolidine-fused β-lactams was developed. The proposed 2,6-diazabicyclo[3.2.0]heptan-7-one scaffolds were constructed through an amido group-induced, potassium <i>tert</i>-butoxide-promoted intramolecular ring closure of 3-acylamino-4-oxiranyl-β-lactams as the key reaction step. Alternatively, the desired cyclization was also effected by means of a scandium triflate-mediated catalytic approach. In this way, a set of stereodefined 3,4-pyrrolidine-fused β-lactams was synthesized, which were preliminary evaluated as β-lactamase inhibitors. These first-line biological assessments led to the identification of a 2-benzoyl-6-(4-methoxyphenyl)-substituted diazabicyclo structure as an eligible starting point for further β-lactamase inhibitor optimization studies.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217018","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
Direct Substitution of 2-Aminotropones with Potassium Allyltrifluoroborates through Transition-Metal-Free C−N Bond Cleavage 烯丙基三氟硼酸钾通过无过渡金属 C-N 键裂解直接取代 2-氨基托品
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-27 DOI: 10.1002/ajoc.202400386
Qian-Qian Wu, Yan Wang, Muliang Zhang, Shi-Kai Tian
{"title":"Direct Substitution of 2-Aminotropones with Potassium Allyltrifluoroborates through Transition-Metal-Free C−N Bond Cleavage","authors":"Qian-Qian Wu,&nbsp;Yan Wang,&nbsp;Muliang Zhang,&nbsp;Shi-Kai Tian","doi":"10.1002/ajoc.202400386","DOIUrl":"10.1002/ajoc.202400386","url":null,"abstract":"<p>The poor nucleofugality of the amino group renders the C−N bond functionalization of primary aromatic amines highly challenging. Herein, we report a direct substitution reaction of 2-aminotropones, bearing a unique non-benzenoid seven-membered aromatic ring that exists in some natural products and bioactive molecules, with potassium allyltrifluoroborates through C−N bond cleavage under transition-metal-free conditions. The amino group of 2-aminotropones were directly substituted with potassium allyltrifluoroborates in the presence of sodium bicarbonate, delivering structurally diverse 2-allyltropones in moderate to good yields. The reaction is free of directing groups, activating groups and transition metals, providing a convenient method to access substituted tropones.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217019","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
DNA-Compatible Nitriles Hydrolysis for Late-Stage Functionalization of DNA-Encoded Libraries 水解与 DNA 相容的腈，实现 DNA 编码文库的后期功能化
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-08-25 DOI: 10.1002/ajoc.202400280
Tianyang Zhang, Xianfu Fang, Xin Wang, Huicong Wang, Gong Zhang, Wei Fang, Yangfeng Li, Yizhou Li
{"title":"DNA-Compatible Nitriles Hydrolysis for Late-Stage Functionalization of DNA-Encoded Libraries","authors":"Tianyang Zhang,&nbsp;Xianfu Fang,&nbsp;Xin Wang,&nbsp;Huicong Wang,&nbsp;Gong Zhang,&nbsp;Wei Fang,&nbsp;Yangfeng Li,&nbsp;Yizhou Li","doi":"10.1002/ajoc.202400280","DOIUrl":"10.1002/ajoc.202400280","url":null,"abstract":"<p>Primary amides play a crucial role in organic and pharmaceutical synthesis. Herein, we present a rapid and convenient method for transforming diverse DNA-conjugated nitriles into primary amides utilizing hydrogen peroxide and potassium carbonate. The substrate scope and DEL compatibility of this reaction were thoroughly investigated, revealing a wide range of substrates with moderate-to-excellent conversion. This on-DNA transformation holds significant promise for constructing DNA-encoded libraries (DELs) and enabling late-stage functionalization to expand chemical diversity. Our approach not only highlights the versatility of the method but also underscores its potential for broad applications in organic and pharmaceutical synthesis.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217020","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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