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Asian Journal of Organic Chemistry最新文献

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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 2.7 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, Wen-Chao Yang, Hegui Fang, Wenchao Yang
{"title":"Synthesis of Naphthalenones via Photo‐Induced Radical Cascade Fluoroalkylation/Cyclization of Alkenes","authors":"Xiaohu Yang, Chunmei Yang, Xiaoqing Wan, Wen-Chao Yang, Hegui Fang, Wenchao Yang","doi":"10.1002/ajoc.202400354","DOIUrl":"https://doi.org/10.1002/ajoc.202400354","url":null,"abstract":"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.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"64 1","pages":""},"PeriodicalIF":2.7,"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 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-09 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, Wozheng Fang, Yu Yan, Nan Sun, Junbiao Chang, Xiao-Na Wang","doi":"10.1002/ajoc.202400416","DOIUrl":"https://doi.org/10.1002/ajoc.202400416","url":null,"abstract":"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.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-09","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 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-09 DOI: 10.1002/ajoc.202400464
Guodu Liu, Yanyan Guo, Meiyu Wang
{"title":"Recent Advances on Regioselective C−H Borylation of Indoles","authors":"Guodu Liu, Yanyan Guo, Meiyu Wang","doi":"10.1002/ajoc.202400464","DOIUrl":"https://doi.org/10.1002/ajoc.202400464","url":null,"abstract":"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.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"36 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-09","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
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 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-06 DOI: 10.1002/ajoc.202400398
Eun-sol Choi, Hyo-Jun Lee, Maruoka Keiji
{"title":"Metal‐Free Generation of Acyl Fluorides via Activation of Cyclopropyl Esters using a Hypervalent Iodine(III) Species and Selectfluor.","authors":"Eun-sol Choi, Hyo-Jun Lee, Maruoka Keiji","doi":"10.1002/ajoc.202400398","DOIUrl":"https://doi.org/10.1002/ajoc.202400398","url":null,"abstract":"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.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"59 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-06","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
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 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-06 DOI: 10.1002/ajoc.202400353
Wenbo Ma, Tao Zheng, Zihan Yu, Junlong Li, Qilin Gu, Linghui Gu, Zheyu Li
{"title":"Solvent‐Free Dehydrogenative C‒H Chalcogenations of Pyrazolones Using Mechanochemistry","authors":"Wenbo Ma, Tao Zheng, Zihan Yu, Junlong Li, Qilin Gu, Linghui Gu, Zheyu Li","doi":"10.1002/ajoc.202400353","DOIUrl":"https://doi.org/10.1002/ajoc.202400353","url":null,"abstract":"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","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":2.7,"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
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 2.7 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, Md. 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, Mohammad Mostafizur Rahman, Md. Mizanur Rahman, Rownok Jahan, Gulshan Ara, Hiroshi Nishino, Mohammad Sayed Alam, Md. Aminul Haque","doi":"10.1002/ajoc.202400363","DOIUrl":"https://doi.org/10.1002/ajoc.202400363","url":null,"abstract":"Twelve thiazole hybrids (2a‐2l) 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 2c had revealed its higher efficacy in both biological studies. It had displayed IC50 of 25.55 ± 0.40 µg/mL which is higher than the standard ascorbic acid (IC50 = 41.31 ± 1.83 µg/mL) as well as dihydrothiazoylchromenone 2e showed promising antioxidant activity with IC50 value of 40.82 ± 0.54. The compound 2c 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 2c revealed its wide range of interactions with different amino acid residues which was also endorsed with the output of molecular dynamics simulation.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.7,"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
Dearomative Addition of Carboranyl Anions to Isoquinolinium Salts and Subsequent Reduction to Access Carborane‐Functionalized Dihydroisoquinolines 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 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-05 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 Dihydroisoquinolines","authors":"Yun-Fan Gao, Chen-Ming Xu, Ming-Hui Yu, Yongna Zhang, Xiao-Jun Wu, You-Qing Wang","doi":"10.1002/ajoc.202400390","DOIUrl":"https://doi.org/10.1002/ajoc.202400390","url":null,"abstract":"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 o‐carborane or m‐carborane.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-05","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
catalytic Dearomative Cycloaddition Reactions enabled by visible light 利用可见光进行催化Dearomative Cycloaddition反应
IF 2.7 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":"https://doi.org/10.1002/ajoc.202400374","url":null,"abstract":"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.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"281 1","pages":""},"PeriodicalIF":2.7,"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
Gold Catalyzed [3+2] Oxidative Annulation of 1,3‐Enyne with Indole 金催化 1,3-炔与吲哚的 [3+2] 氧化环化反应
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-03 DOI: 10.1002/ajoc.202400356
Zili Chen, Qiang Zou, Yu-Jiang Wang, Ya-Ru Wan
{"title":"Gold Catalyzed [3+2] Oxidative Annulation of 1,3‐Enyne with Indole","authors":"Zili Chen, Qiang Zou, Yu-Jiang Wang, Ya-Ru Wan","doi":"10.1002/ajoc.202400356","DOIUrl":"https://doi.org/10.1002/ajoc.202400356","url":null,"abstract":"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 N‐oxide 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 & hydrazone derivative’s 1,5‐ electrocyclization have been performed.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"59 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-03","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‐Phenylquinoline 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 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-03 DOI: 10.1002/ajoc.202400394
Hongjun Zhu, Tongtong Deng, Shan Hu, Xianyu Ying, Hui Wang
{"title":"Palladium Catalyzed Direct Ortho C‐H Acylation of 4‐Phenylquinoline using Methylarenes as Acylation Reagents","authors":"Hongjun Zhu, Tongtong Deng, Shan Hu, Xianyu Ying, Hui Wang","doi":"10.1002/ajoc.202400394","DOIUrl":"https://doi.org/10.1002/ajoc.202400394","url":null,"abstract":"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.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-03","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
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