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Asian Journal of Organic Chemistry最新文献

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One‐Pot Synthesis of 2‐Substituted Indoles and 7‐Azaindoles via Sequential Alkynylation and Cyclization of 2‐Iodo‐N‐mesylarylamines and Alkynes in the Presence of Cu2O 在Cu2O存在下，2-碘- n -甲酰基胺和炔酮序烷基化和环化一锅法合成2-取代吲哚和7-氮杂吲哚。
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400421
Ahmed R. Ali , Longqin Hu
{"title":"One‐Pot Synthesis of 2‐Substituted Indoles and 7‐Azaindoles via Sequential Alkynylation and Cyclization of 2‐Iodo‐N‐mesylarylamines and Alkynes in the Presence of Cu2O","authors":"Ahmed R. Ali ,&nbsp;Longqin Hu","doi":"10.1002/ajoc.202400421","DOIUrl":"10.1002/ajoc.202400421","url":null,"abstract":"<div><div>A one‐pot process was developed to synthesize in moderate to high yield a series of 2‐substituted indoles and 7‐azaindoles starting from 2‐iodo‐<em>N</em>‐mesylarylamines and terminal alkynes in the presence of Cu<sub>2</sub>O in DMF at 90–120 °C. Without isolation of any intermediate, our optimized conditions enabled the introduction of ester, phenyl, hydroxymethyl, hydroxyethyl, <em>N</em>‐Boc‐aminomethyl, and methyl at the 2‐postion of indoles and 7‐azaindoles. The reaction tolerates a variety of substrates containing halogens, or acid‐ or base‐sensitive functional groups without requiring a Pd catalyst, a ligand, or a base.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400421"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11741182/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142996787","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
Stepwise Conversion of a 10‐Membered Diketo Open‐Cage [60]Fullerene to a 10‐Membered Keto‐Lactone Open‐Cage [60]Fullerene
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400590
Yiran Wu , Yaqiong Wang , Yulin Guo , Prof. Dr. Yuming Yu , Dr. Jie Su , Dr. Yi Qiu , Prof. Dr. Liangbing Gan
{"title":"Stepwise Conversion of a 10‐Membered Diketo Open‐Cage [60]Fullerene to a 10‐Membered Keto‐Lactone Open‐Cage [60]Fullerene","authors":"Yiran Wu ,&nbsp;Yaqiong Wang ,&nbsp;Yulin Guo ,&nbsp;Prof. Dr. Yuming Yu ,&nbsp;Dr. Jie Su ,&nbsp;Dr. Yi Qiu ,&nbsp;Prof. Dr. Liangbing Gan","doi":"10.1002/ajoc.202400590","DOIUrl":"10.1002/ajoc.202400590","url":null,"abstract":"<div><div>The chemical reactivity of a 10‐membered diketo open‐cage fullerene C<sub>60</sub>(O)<sub>2</sub>(OO<em>t</em>Bu)<sub>4</sub> was investigated in an effort to reveal the unique reaction pattern of fullerene derivatives. Selective cleavage of peroxo O−O bonds was observed under thermolysis in the presence of iodine to form epoxy groups around the orifice. Opening of the epoxy groups leads to vicinal diol moiety, oxidation of which resulted in a new 10‐membered keto‐lactone open‐cage fullerene derivative. Single crystal X‐ray diffraction analysis showed that the size of the rectangular orifice is around 2.96×4.66 Å.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400590"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143113934","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 Alkylated Carbonyl‐Bearing Furans via Acid‐Catalyzed Friedel‐Crafts Reaction
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400335
Ilya M. Tkachenko , Natalia A. Ivanova , Kristina S. Khrapovitskaya , Yuri N. Klimochkin
{"title":"Synthesis of Alkylated Carbonyl‐Bearing Furans via Acid‐Catalyzed Friedel‐Crafts Reaction","authors":"Ilya M. Tkachenko ,&nbsp;Natalia A. Ivanova ,&nbsp;Kristina S. Khrapovitskaya ,&nbsp;Yuri N. Klimochkin","doi":"10.1002/ajoc.202400335","DOIUrl":"10.1002/ajoc.202400335","url":null,"abstract":"<div><div>Carbonyl‐bearing furans, certain pyrroles, and thiophenes were alkylated using alcohols in an acidic medium. Some 5‐alkylated derivatives of 2‐furoic acid with various adamantyls‐, cycloalkyl‐, other 2°‐ and 3°‐alkyl substituents were synthesized using 2‐furoic acid as a biomass‐derived chemical platform. Side reaction resulted in the substitution of the carboxylic group, leading to the formation of 1,5‐dialkyl furans. In the alkylation of acyl and formyl furan, either mono‐ or di‐alkyl products were obtained, depending on the functional group present in the furan nucleus. Pyrroles (or thiophenes) with related functional groups exclusively (or near‐exclusively) yielded mono‐alkyl products. The resultant 5‐substituted carbonyl furans can be used as building blocks and synthetic equivalents for 1 C and 4 C synthons, as demonstrated by a series of reactions involving 5‐adamantan‐1‐yl‐2‐furoic acid.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400335"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114146","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
Continuous Flow Synthesis of Five‐Membered N‐Heterocycles by Ynone System
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400359
Tamilselvan Duraisamy , Vijay Thavasianandam Seenivasan , Li‐Yu Wang , Dr. Karthick Govindan , Dr. Balaji Ganesan , Dr. Mohanraj Kandasamy , Yu‐Ting Chiou , Prof. Dr. Wei‐Yu Lin
{"title":"Continuous Flow Synthesis of Five‐Membered N‐Heterocycles by Ynone System","authors":"Tamilselvan Duraisamy ,&nbsp;Vijay Thavasianandam Seenivasan ,&nbsp;Li‐Yu Wang ,&nbsp;Dr. Karthick Govindan ,&nbsp;Dr. Balaji Ganesan ,&nbsp;Dr. Mohanraj Kandasamy ,&nbsp;Yu‐Ting Chiou ,&nbsp;Prof. Dr. Wei‐Yu Lin","doi":"10.1002/ajoc.202400359","DOIUrl":"10.1002/ajoc.202400359","url":null,"abstract":"<div><div>In this study, we devised a practical and effective method for synthesizing ynones from terminal alkynes and anhydride utilizing a continuous flow apparatus at ambient temperature. Moreover, we coupled the ynones with hydrazines, and hydroxylamine hydrochloride to synthesize pyrazole and isoxazole derivatives. This protocol's unique characteristics include a metal‐free approach, mild reaction conditions, a short residence time, and a wide range of functional group tolerance. Sustainable strategies are most useful and affordable than conventional benchtop approaches.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400359"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115787","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
Heterogeneous Catalytic Materials for Carbon dioxide Transformation: Efficient Carboxylation Cyclization to Cyclic Carbonates and Oxazolidinones
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400492
Zhongyang Ma , Peibo Chen , Chancui Wu , Ying Liang , Yingming Pan
{"title":"Heterogeneous Catalytic Materials for Carbon dioxide Transformation: Efficient Carboxylation Cyclization to Cyclic Carbonates and Oxazolidinones","authors":"Zhongyang Ma ,&nbsp;Peibo Chen ,&nbsp;Chancui Wu ,&nbsp;Ying Liang ,&nbsp;Yingming Pan","doi":"10.1002/ajoc.202400492","DOIUrl":"10.1002/ajoc.202400492","url":null,"abstract":"<div><div>The exacerbation of environmental issues is increasingly attributed to the anthropogenic emissions of carbon dioxide (CO<sub>2</sub>). CO<sub>2</sub> is a cost‐effective and readily available C1 source. The conversion of CO<sub>2</sub> into value‐added organic chemicals, such as cyclic carbonate and 2‐oxazolidinone, through carboxylation cyclization reactions shows promise in reducing carbon emissions and combating climate change. The use of catalysts can facilitate this process, with heterogeneous catalysts emerging as favorable due to their advantages of easy recovery and structural stability. This paper provides a comprehensive review of heterogeneous catalysts that have been utilized for the carboxylation cyclization of CO<sub>2</sub> to afford cyclic carbonates and oxazolidinones in recent years. The catalysts include metal organic frameworks, covalent organic frameworks, super‐crosslinked polymers, conjugated microporous polymers, porous ionic organic polymers, and composite materials. We give a detailed synthesis route for each type of catalysts. Furthermore, the characteristics of the catalysts, such as BET specific surface area, CO<sub>2</sub> adsorption capacity, and catalytic performance, is summarized and analyzed to offer insights for improving heterogeneous catalysts for CO<sub>2</sub> conversion via carboxylation cyclization reactions in future research.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400492"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143118538","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
Furfural: An Efficient Platform Molecule as a CO Surrogate in Palladium Catalysed Synthesis of α, β‐Alkynylamides
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400507
Shraddha D. Shinde , Nina Kuchkina , Bhalchandra M. Bhanage , Zinaida Shifrina
{"title":"Furfural: An Efficient Platform Molecule as a CO Surrogate in Palladium Catalysed Synthesis of α, β‐Alkynylamides","authors":"Shraddha D. Shinde ,&nbsp;Nina Kuchkina ,&nbsp;Bhalchandra M. Bhanage ,&nbsp;Zinaida Shifrina","doi":"10.1002/ajoc.202400507","DOIUrl":"10.1002/ajoc.202400507","url":null,"abstract":"<div><div>Biomass‐derived furfural was used as a CO surrogate for the first time in the oxidative N‐dealkylation/carbonylation of various aliphatic and cyclic tertiary amines with terminal alkynes to produce alk‐2‐ynamides. This reaction employed O<sub>2</sub> as an ideal oxidising agent and used a Pd/C catalyst with KI as an additive in a base free and ligand free condition. Notably, the selective sp<sup>3</sup> C−N bond cleavage of tertiary amines led to its potential application as an amine source. The typical and simple route provides another option for producing a broad variety of alk‐2‐ynamide derivatives in environmentally friendly and efficient way under mild conditions. This method also displays notable reusability.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400507"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143119173","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 Acylation of Vinylcyclopropanes under Visible‐Light Photocatalysis
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400325
Chenna Jagadeesh , Manveer Patel , Subhadeep Hazra , Sandipan Mondal , Anand B. Melkani , Jaideep Saha
{"title":"Site‐Selective Acylation of Vinylcyclopropanes under Visible‐Light Photocatalysis","authors":"Chenna Jagadeesh ,&nbsp;Manveer Patel ,&nbsp;Subhadeep Hazra ,&nbsp;Sandipan Mondal ,&nbsp;Anand B. Melkani ,&nbsp;Jaideep Saha","doi":"10.1002/ajoc.202400325","DOIUrl":"10.1002/ajoc.202400325","url":null,"abstract":"<div><div>We herein disclose a protocol for linear‐selective ring‐opening acylation of a range of electron‐poor VCPs with α‐ketoacids by Ir‐photocatalyst. While electron‐poor VCPs could be sensitized with various radical species generated under different reaction conditions including photo‐redox processes, exploring similar repertoire with acyl radical remains unexplored. Since the linear selective ring opening leads to translocation of the vinylic olefin into an internal one, terminal addition of VCP systems with electronically diverse groups present at the terminus, permitting formation of tailored of building blocks.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400325"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115788","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 2‐Pyrones by Base‐Induced [3+3] Annulation Reaction of Phenacyl Phosphonium Ylides with Cyclopropenones
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400333
Yuanyuan Zhang , Xiaoyu Wang , Jiangwei Wen , Qiuyun Li , Wenyue Xue , Hancong Liu , Kelu Yan
{"title":"Synthesis of 2‐Pyrones by Base‐Induced [3+3] Annulation Reaction of Phenacyl Phosphonium Ylides with Cyclopropenones","authors":"Yuanyuan Zhang ,&nbsp;Xiaoyu Wang ,&nbsp;Jiangwei Wen ,&nbsp;Qiuyun Li ,&nbsp;Wenyue Xue ,&nbsp;Hancong Liu ,&nbsp;Kelu Yan","doi":"10.1002/ajoc.202400333","DOIUrl":"10.1002/ajoc.202400333","url":null,"abstract":"<div><div>The base‐induced [3+3] annulation reaction of phenacyl phosphonium ylides with cyclopropenones has been proposed. Various polysubstituted 2‐pyrones are achieved in moderate to good yields through C−P bond cleavage and C−O/C−C coupling under simple and easy‐to‐operate conditions. The synthetic application and reaction mechanism have also been preliminarily explored to gain a deeper understanding of this strategy in practicality and reaction details. This protocol offers an alternative approach for the synthesis of useful 2‐pyrone derivatives.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400333"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143116274","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
Cu‐Catalyzed Oxidative Tandem Coupling and Cyclization of 2‐Aminonaphthalenes to Synthesize Dibenzo[c, g]carbazoles
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400366
Minwoo Kong , Arnab Ghosh , Myung Hwan Park , Min Kim , Houng Kang
{"title":"Cu‐Catalyzed Oxidative Tandem Coupling and Cyclization of 2‐Aminonaphthalenes to Synthesize Dibenzo[c, g]carbazoles","authors":"Minwoo Kong ,&nbsp;Arnab Ghosh ,&nbsp;Myung Hwan Park ,&nbsp;Min Kim ,&nbsp;Houng Kang","doi":"10.1002/ajoc.202400366","DOIUrl":"10.1002/ajoc.202400366","url":null,"abstract":"<div><div>A Cu(II) complex with a bipyridyl ligand bearing a Brønsted acid was used to catalyze the tandem oxidative coupling and cyclization of 2‐aminonaphthalenes to give <em>N</em>‐substituted‐dibenzo[<em>c,g</em>]carbazoles. The incorporation of an appended acidic moiety to the ligand was found to be key to the selective formation of dibenzocarbazoles over 2,2’‐diamino‐1,1’‐binaphthalene (BINAM), which is known as an irreversible byproduct. This highly efficient method yields a wide array of dibenzo[<em>c,g</em>]carbazoles featuring diverse functional groups as well as electronic properties. The selected dibenzo[<em>c,g</em>]carbazoles exhibited high photoluminescence quantum yields of up to 100 % and are promising chromophores for advanced materials.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400366"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143119269","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
Ring Expansion from 16‐Membered Macrocyclic Lactones Using Yamaguchi and Photoinduced Decarboxylative Radical Macrolactonization
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI: 10.1002/ajoc.202400560
Ryoga Hashimoto , Kenta Kameda , Shoki Kuresawa , Tomoya Iwasaki , Prof. Toshiki Furutani , Prof. Mugen Yamawaki , Prof. Hirotsugu Suzuki , Prof. Yasuharu Yoshimi
{"title":"Ring Expansion from 16‐Membered Macrocyclic Lactones Using Yamaguchi and Photoinduced Decarboxylative Radical Macrolactonization","authors":"Ryoga Hashimoto ,&nbsp;Kenta Kameda ,&nbsp;Shoki Kuresawa ,&nbsp;Tomoya Iwasaki ,&nbsp;Prof. Toshiki Furutani ,&nbsp;Prof. Mugen Yamawaki ,&nbsp;Prof. Hirotsugu Suzuki ,&nbsp;Prof. Yasuharu Yoshimi","doi":"10.1002/ajoc.202400560","DOIUrl":"10.1002/ajoc.202400560","url":null,"abstract":"<div><div>This study describes a new strategy for synthesizing 31‐, 33‐, 46‐, and 48‐membered macrocyclic lactones from commercially available 16‐membered macrocyclic lactones using the Yamaguchi reaction and photoinduced decarboxylative radical macrolactonization. Despite challenges with the low solubility of substrates and the slow rate of photochemical radical cyclization, the preparation of enlarged macrocyclic lactones from 16‐membered macrocyclic lactones was successfully accomplished. Additionally, the effect of the Lewis acidity of the counter cation in the carboxylate salt provided mechanistic insights into the photoinduced decarboxylative radical macrolactonization.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 1","pages":"Article e202400560"},"PeriodicalIF":2.8,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400560","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143110589","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
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