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[3 + 2] Cycloaddition of N-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-a]quinoline and Pyrazolo[5,1-a]isoquinoline Derivatives [3 + 2] n -氨基（异）喹啉盐与乙烯基磺酸盐的环加成：吡唑啉[1,5-a]喹啉和吡唑啉[5,1-a]异喹啉衍生物的合成
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-16 DOI: 10.1021/acs.joc.5c00377
Hui Wu, Wenfeng Zhao, Nan Jiang, Mao Liu, Qingmei Ge, Hang Cong
{"title":"[3 + 2] Cycloaddition of N-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-a]quinoline and Pyrazolo[5,1-a]isoquinoline Derivatives","authors":"Hui Wu, Wenfeng Zhao, Nan Jiang, Mao Liu, Qingmei Ge, Hang Cong","doi":"10.1021/acs.joc.5c00377","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00377","url":null,"abstract":"In this study, we reported the utilization of vinylsulfonium salt as a highly efficient dipolarophile, leveraging the facile leaving ability of its sulfide moiety, to engage in a [3 + 2] cycloaddition with <i>N</i>-amino(iso)quinolinium salts. This approach facilitates the construction of various C<sub>1</sub>/C<sub>2</sub>-unsubstituted pyrazolo(iso)quinoline skeletons. The transformation is conducted under catalyst- and external oxidant-free conditions. Furthermore, the extended gram-scale reaction demonstrates the practical applicability of the developed protocol.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144066178","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
[3 + 2] Cycloaddition of N-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-a]quinoline and Pyrazolo[5,1-a]isoquinoline Derivatives [3 + 2] n -氨基（异）喹啉盐与乙烯基磺酸盐的环加成：吡唑啉[1,5-a]喹啉和吡唑啉[5,1-a]异喹啉衍生物的合成
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-16 DOI: 10.1021/acs.joc.5c0037710.1021/acs.joc.5c00377
Hui Wu, Wenfeng Zhao, Nan Jiang, Mao Liu, Qingmei Ge* and Hang Cong, 
{"title":"[3 + 2] Cycloaddition of N-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-a]quinoline and Pyrazolo[5,1-a]isoquinoline Derivatives","authors":"Hui Wu,&nbsp;Wenfeng Zhao,&nbsp;Nan Jiang,&nbsp;Mao Liu,&nbsp;Qingmei Ge* and Hang Cong,&nbsp;","doi":"10.1021/acs.joc.5c0037710.1021/acs.joc.5c00377","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00377https://doi.org/10.1021/acs.joc.5c00377","url":null,"abstract":"<p >In this study, we reported the utilization of vinylsulfonium salt as a highly efficient dipolarophile, leveraging the facile leaving ability of its sulfide moiety, to engage in a [3 + 2] cycloaddition with <i>N</i>-amino(iso)quinolinium salts. This approach facilitates the construction of various C<sub>1</sub>/C<sub>2</sub>-unsubstituted pyrazolo(iso)quinoline skeletons. The transformation is conducted under catalyst- and external oxidant-free conditions. Furthermore, the extended gram-scale reaction demonstrates the practical applicability of the developed protocol.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 21","pages":"6969–6979 6969–6979"},"PeriodicalIF":3.3,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144165844","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles. 可见光诱导级联磷酸化/环化以获得含磷重氮氨基咔唑。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-16 DOI: 10.1021/acs.joc.5c00713
Yifan Yin,Fei Liu,Miao Tian,Liangliang Han,Minghan Li,Jianfeng Tao,Qian Liu,Lianglong Sun,Xinming Xu,Kai Sun
{"title":"Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles.","authors":"Yifan Yin,Fei Liu,Miao Tian,Liangliang Han,Minghan Li,Jianfeng Tao,Qian Liu,Lianglong Sun,Xinming Xu,Kai Sun","doi":"10.1021/acs.joc.5c00713","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00713","url":null,"abstract":"Herein, we developed a novel radical cascade phosphorylation/cyclization strategy to access phosphorus-containing diazocine-fused carbazoles in moderate to good yields, offering expanded opportunities for the exploration of biologically active molecules. This method features metal-free photochemical tandem, mild conditions, broad substrate scopes, and scale-up ability. Mechanistic experiments implied that this photocatalyzed phosphorylation/cyclization reaction was realized by a sequence of EnT/SET/SET/radical addition/cyclization/SET/deprotonation processes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144065685","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles 可见光诱导级联磷酸化/环化以获得含磷重氮氨基咔唑
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-16 DOI: 10.1021/acs.joc.5c0071310.1021/acs.joc.5c00713
Yifan Yin, Fei Liu, Miao Tian*, Liangliang Han*, Minghan Li, Jianfeng Tao, Qian Liu, Lianglong Sun, Xinming Xu* and Kai Sun*, 
{"title":"Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles","authors":"Yifan Yin,&nbsp;Fei Liu,&nbsp;Miao Tian*,&nbsp;Liangliang Han*,&nbsp;Minghan Li,&nbsp;Jianfeng Tao,&nbsp;Qian Liu,&nbsp;Lianglong Sun,&nbsp;Xinming Xu* and Kai Sun*,&nbsp;","doi":"10.1021/acs.joc.5c0071310.1021/acs.joc.5c00713","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00713https://doi.org/10.1021/acs.joc.5c00713","url":null,"abstract":"<p >Herein, we developed a novel radical cascade phosphorylation/cyclization strategy to access phosphorus-containing diazocine-fused carbazoles in moderate to good yields, offering expanded opportunities for the exploration of biologically active molecules. This method features metal-free photochemical tandem, mild conditions, broad substrate scopes, and scale-up ability. Mechanistic experiments implied that this photocatalyzed phosphorylation/cyclization reaction was realized by a sequence of EnT/SET/SET/radical addition/cyclization/SET/deprotonation processes.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 21","pages":"7070–7080 7070–7080"},"PeriodicalIF":3.3,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144165841","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
A One-Pot Synthesis of Substituted Pyrrolo[2,1-a]isoquinolines via an Oxidation/Annulation Sequence of 2-(3,4-Dihydroisoquinolin-2(1H)-yl)malononitriles. 2-（3,4-二氢异喹啉-2(1H)-基）丙二腈的氧化/环化序列一锅法合成取代吡咯[2,1- A]异喹啉
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00639
Bang-Hong Zhang,Kai-Long Hou,Run-Ze Li,Fang-Fang Qiu,Ge-Ge Liu,Zi-Qin Wei,Wen Bao,Ye Zhang,Dao-Yong Zhu,Shao-Hua Wang
{"title":"A One-Pot Synthesis of Substituted Pyrrolo[2,1-a]isoquinolines via an Oxidation/Annulation Sequence of 2-(3,4-Dihydroisoquinolin-2(1H)-yl)malononitriles.","authors":"Bang-Hong Zhang,Kai-Long Hou,Run-Ze Li,Fang-Fang Qiu,Ge-Ge Liu,Zi-Qin Wei,Wen Bao,Ye Zhang,Dao-Yong Zhu,Shao-Hua Wang","doi":"10.1021/acs.joc.5c00639","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00639","url":null,"abstract":"A highly effective oxidation/annulation reaction between 2-isocyanoacetates and 2-(3,4-dihydroisoquinolin-2(1H)-yl)malononitriles has been successfully developed to give substituted pyrrolo[2,1-a]isoquinoline derivatives with moderate to good yields in a one-pot manner.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143991994","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Bifunctional Ionic Liquids Induced Electrochemical C-H Arylation of Quinoxalin(on)es with Aryltriazenes. 双功能离子液体诱导喹啉与芳基三氮烯的C-H电化学芳基化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00460
Chenyu Li,Wei Xu,Bin Wang,Ziren Chen,Yu Xia,Shaofeng Wu,Weiwei Jin,Chenjiang Liu,Yonghong Zhang
{"title":"Bifunctional Ionic Liquids Induced Electrochemical C-H Arylation of Quinoxalin(on)es with Aryltriazenes.","authors":"Chenyu Li,Wei Xu,Bin Wang,Ziren Chen,Yu Xia,Shaofeng Wu,Weiwei Jin,Chenjiang Liu,Yonghong Zhang","doi":"10.1021/acs.joc.5c00460","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00460","url":null,"abstract":"An efficient bifunctional ionic-liquid-induced electrochemical C-H arylation of quinoxalin(on)es with aryltriazenes has been developed. The reaction utilizes aryltriazenes as stable arylation reagents and ionic liquids as promoter and electrolyte. Various arylated quinoxalin-2(1H)-ones, quinoxaline and 2-methyldibenzo[f,h]quinoxaline were assembled in modest to excellent yields under mild, metal- and oxidant-free conditions. The developed protocol features simple operation, good functional group tolerance, good selectivity, product derivatization, and practical gram-scale synthesis in batch and continuous-flow processes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"22 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143982527","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Electrophilic (Hetero)Arene C-H Nitration by Ferric Nitrate Nonahydrate in Hexafluoroisopropanol. 非水合硝酸铁在六氟异丙醇中硝化亲电（杂）芳烃的研究。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00137
Yuzhu Zheng,Zongyi Liu,Zhaobo Ying,Youwei Xie
{"title":"Electrophilic (Hetero)Arene C-H Nitration by Ferric Nitrate Nonahydrate in Hexafluoroisopropanol.","authors":"Yuzhu Zheng,Zongyi Liu,Zhaobo Ying,Youwei Xie","doi":"10.1021/acs.joc.5c00137","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00137","url":null,"abstract":"In this article, we provide an extended substrate scope and more detailed mechanistic studies of an operationally simple and generally applicable arene nitration that we previously reported. This method utilizes safe and inexpensive Fe(NO3)3•9H2O as the nitro source in easily recyclable HFIP and obviates the need for corrosive acids (HNO3 + H2SO4). As a result, we speculated that it could serve as an effective substitute for the traditional mixed acid approach under most scenarios due to its operational simplicity. A general guidance for the application of this method was provided.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143991992","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
A One-Pot Relay Sc(III)/Base-Promoted Addition/Cyclization of 1-(o-Aminophenyl)prop-2-Ynols and S/C Nucleophiles: Synthesis of 3-Sulfenylindole and 3-Arylindole Derivatives. 1-（邻氨基苯基）2-丙炔醇和S/C亲核试剂的一锅接力Sc(III)/碱促进加成/环化：3-亚砜酰吲哚和3-芳酰吲哚衍生物的合成。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c00182
Chang He,Xiao-Han Qiu,Yi-Feng Lin,Ming Bian,Hui-Yu Chen,Yu-Ning Gao,Zhen-Jiang Liu
{"title":"A One-Pot Relay Sc(III)/Base-Promoted Addition/Cyclization of 1-(o-Aminophenyl)prop-2-Ynols and S/C Nucleophiles: Synthesis of 3-Sulfenylindole and 3-Arylindole Derivatives.","authors":"Chang He,Xiao-Han Qiu,Yi-Feng Lin,Ming Bian,Hui-Yu Chen,Yu-Ning Gao,Zhen-Jiang Liu","doi":"10.1021/acs.joc.5c00182","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00182","url":null,"abstract":"An efficient strategy for the construction of 3-sulfenylindoles and 3-arylindoles based on a one-pot relay Sc(III)/base-promoted Michael addition/cyclization/aromatization process has been developed. Different types of nucleophiles (thio- and carbon nucleophiles) react with aza-alkynyl o-quinone methides (aza-o-AQMs) generated in situ from 1-(o-aminophenyl)prop-2-ynols to afford the indole derivatives in moderate to excellent yields. This method displays the advantages of mild conditions, simple starting materials, and broad substrate scope.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"130 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144065687","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Bifunctional Ionic Liquids Induced Electrochemical C–H Arylation of Quinoxalin(on)es with Aryltriazenes 双功能离子液体诱导喹啉与芳基三氮烯的C-H电化学芳基化反应
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c0046010.1021/acs.joc.5c00460
Chenyu Li, Wei Xu, Bin Wang, Ziren Chen, Yu Xia, Shaofeng Wu, Weiwei Jin, Chenjiang Liu* and Yonghong Zhang*, 
{"title":"Bifunctional Ionic Liquids Induced Electrochemical C–H Arylation of Quinoxalin(on)es with Aryltriazenes","authors":"Chenyu Li,&nbsp;Wei Xu,&nbsp;Bin Wang,&nbsp;Ziren Chen,&nbsp;Yu Xia,&nbsp;Shaofeng Wu,&nbsp;Weiwei Jin,&nbsp;Chenjiang Liu* and Yonghong Zhang*,&nbsp;","doi":"10.1021/acs.joc.5c0046010.1021/acs.joc.5c00460","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00460https://doi.org/10.1021/acs.joc.5c00460","url":null,"abstract":"<p >An efficient bifunctional ionic-liquid-induced electrochemical C–H arylation of quinoxalin(on)es with aryltriazenes has been developed. The reaction utilizes aryltriazenes as stable arylation reagents and ionic liquids as promoter and electrolyte. Various arylated quinoxalin-2(1<i>H</i>)-ones, quinoxaline and 2-methyldibenzo[<i>f,h</i>]quinoxaline were assembled in modest to excellent yields under mild, metal- and oxidant-free conditions. The developed protocol features simple operation, good functional group tolerance, good selectivity, product derivatization, and practical gram-scale synthesis in batch and continuous-flow processes.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 20","pages":"6891–6896 6891–6896"},"PeriodicalIF":3.3,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144114647","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Organocatalytic Synthesis of Spiro-Bridged Heterocyclic Compounds via a Chemoselective Vinylogous Michael/Cyclization/Rearrangement Sequence 通过化学选择性链化Michael/环化/重排序列的有机催化合成螺旋桥接杂环化合物
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-05-15 DOI: 10.1021/acs.joc.5c0044310.1021/acs.joc.5c00443
I-Ting Chen, Hsuan Lin and Jeng-Liang Han*, 
{"title":"Organocatalytic Synthesis of Spiro-Bridged Heterocyclic Compounds via a Chemoselective Vinylogous Michael/Cyclization/Rearrangement Sequence","authors":"I-Ting Chen,&nbsp;Hsuan Lin and Jeng-Liang Han*,&nbsp;","doi":"10.1021/acs.joc.5c0044310.1021/acs.joc.5c00443","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00443https://doi.org/10.1021/acs.joc.5c00443","url":null,"abstract":"<p >An organocatalytic cascade reaction of 2-ethylidene 1,3-indandiones and isatylidene-malononitriles has been achieved using quinine as the catalyst. The unexpected vinylogous Michael addition at the β position of isatylidene-malononitriles, followed by aldol cyclization, 1,2-addition of alkoxide to nitrile, and [1,3]-O-to-N rearrangement, leads to the generation of unique spiro-bridged heterocyclic compounds containing amide, indanone, and oxindole moieties in good to excellent yields with high diastereoselectivity.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 21","pages":"7125–7133 7125–7133"},"PeriodicalIF":3.3,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.joc.5c00443","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144165950","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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