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Triplet Ketone Catalysis-Enabled Functionalization of Thioanisoles with Maleimides. 三联体酮催化马来酰亚胺功能化硫苯甲醚。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-18 DOI: 10.1021/acs.joc.5c00794
Akash Bisoyi,Ramsiya Poolamanna,Alisha Rani Tripathy,Veera Reddy Yatham
{"title":"Triplet Ketone Catalysis-Enabled Functionalization of Thioanisoles with Maleimides.","authors":"Akash Bisoyi,Ramsiya Poolamanna,Alisha Rani Tripathy,Veera Reddy Yatham","doi":"10.1021/acs.joc.5c00794","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00794","url":null,"abstract":"Considering the importance of sulfur-containing organic molecules in various domains of chemistry, we report herein a protocol for the catalytic diastereoselective synthesis of tricyclic heterocycles through α-C(sp3)-H functionalization of thioanisoles with maleimides enabled by triplet ketone catalysis. Mild reaction conditions, an inexpensive photocatalyst, molecular oxygen as a terminal oxidant, and compatibility with various functional groups are advantages of the protocol. Preliminary mechanistic studies suggest the generation of α-thioalkyl radicals and involvement of aerial oxygen in our reaction conditions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311645","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
TBHP/I2 Synergistically Promoted Three-Component Reaction of Isatins, Amines and Methylhetarenes: Transition-Metal-Free Access to 2-Hetarylquinazolin-4(3H)-ones. TBHP/I2协同促进Isatins、胺和甲基六烯三组分反应：2-Hetarylquinazolin-4(3H)-ones的无过渡金属获取。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-18 DOI: 10.1021/acs.joc.5c00938
Cheng Xu,Tao Peng,Minglin Liu,Mengyuan Zhou,Qianqian Zhai,Yifei Wang,Yuan Chen,Zheng Liu,Guodong Yin
{"title":"TBHP/I2 Synergistically Promoted Three-Component Reaction of Isatins, Amines and Methylhetarenes: Transition-Metal-Free Access to 2-Hetarylquinazolin-4(3H)-ones.","authors":"Cheng Xu,Tao Peng,Minglin Liu,Mengyuan Zhou,Qianqian Zhai,Yifei Wang,Yuan Chen,Zheng Liu,Guodong Yin","doi":"10.1021/acs.joc.5c00938","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00938","url":null,"abstract":"A TBHP/I2 synergistically promoted three-component reaction of readily available isatins, amines, and methylhetarenes has been established. This transition-metal-free approach provides a concise and practical pathway for the assembly of structurally novel 2-hetarylquinazolin-4(3H)-ones, featuring a wide substrate scope and excellent functional group tolerance. Mechanistic investigations revealed that the TBHP-mediated Baeyer-Villiger-type rearrangement of isatins and the I2-promoted sp3 C-H functionalization of methylhetarenes constituted crucial steps within the reaction sequences. Furthermore, gram-scale synthesis and late-stage modification of the resulting products were successfully implemented.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"626 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311647","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
Regioselective and Chemodivergent Synthesis of 1,3-Indandione-Fused Spirocyclopentenes and Spiropyrrolidines. 1,3-茚二酮融合螺环戊烯和螺吡咯烷的区域选择性和化学发散性合成。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00490
Nabin Parui,Pratap Paul,Sk Jubayar Ahashan,Jyotirmayee Dash
{"title":"Regioselective and Chemodivergent Synthesis of 1,3-Indandione-Fused Spirocyclopentenes and Spiropyrrolidines.","authors":"Nabin Parui,Pratap Paul,Sk Jubayar Ahashan,Jyotirmayee Dash","doi":"10.1021/acs.joc.5c00490","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00490","url":null,"abstract":"Herein, we report a divergent cyclization strategy for the synthesis of 1,3-indandione-fused five-membered carbocyclic and heterocyclic scaffolds. The reaction between 2-arylidene-1,3-indandiones and β-keto enamines gives Michael adducts─1,3-indandione-substituted β-keto enamines─which were used as reaction precursors. Subsequent reaction of these precursors with Cu(OAc)2 leads to the formation of 1,3-indandione-fused spirocyclopentenes via C-C bond formation. In contrast, treatment with N-iodosuccinimide yields diastereoselective spiropyrrolidine derivatives via C-N bond formation. Both reaction pathways proceed with high chemoselectivity, exhibit excellent functional group tolerance, and afford good to excellent yields of the desired products. An ionic mechanism is proposed for the formation of these two classes of spiro-compounds, as supported by radical scavenging experiments.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311331","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
Ligand-Free Silver Fluoride-Promoted (3 + 2) Annulation of Oxaziridines and α-Isocyanoacetates: A Diastereoselective Route to cis-Imidazolines. 无配体氟化银促进恶氮吡啶和α-异氰乙酸酯的（3 + 2）环化：顺式咪唑啉的非对映选择性途径。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00592
Jubao Zhou,Siyun Wang,Hu Shi,Hui Jin,Lixin Zhang
{"title":"Ligand-Free Silver Fluoride-Promoted (3 + 2) Annulation of Oxaziridines and α-Isocyanoacetates: A Diastereoselective Route to cis-Imidazolines.","authors":"Jubao Zhou,Siyun Wang,Hu Shi,Hui Jin,Lixin Zhang","doi":"10.1021/acs.joc.5c00592","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00592","url":null,"abstract":"A ligand-free silver fluoride-promoted diastereoselective (3 + 2) annulation reaction between oxaziridines and isocyanoacetates was developed, enabling the efficient synthesis of cis-2-imidazolines under mild conditions (room temperature within 10 min) with up to 90% yield. The resulting cis-imidazolines are readily hydrolyzed to anti-α,β-diamino acid derivatives while maintaining the stereochemical integrity. Additionally, the cis-imidazolines can be efficiently converted to their trans epimers in high yields, providing stereodivergent access to the syn-α,β-diamino acid derivatives.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311334","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
Mechanistic Insights into Pd-Catalyzed Hydrofunctionalization of 1,3-Dienes: A Theoretical Study. pd催化1,3-二烯加氢功能化的机理：理论研究。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00869
Mouxin Huang,He Liu,Yu-Chao Meng,Wu-Tao Gui,Hou-Qi Zhu,Ying-Chun Chen,Lei Zhu,Xiao-Wei Qi,Qin Ouyang
{"title":"Mechanistic Insights into Pd-Catalyzed Hydrofunctionalization of 1,3-Dienes: A Theoretical Study.","authors":"Mouxin Huang,He Liu,Yu-Chao Meng,Wu-Tao Gui,Hou-Qi Zhu,Ying-Chun Chen,Lei Zhu,Xiao-Wei Qi,Qin Ouyang","doi":"10.1021/acs.joc.5c00869","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00869","url":null,"abstract":"The generation of the π-allylpalladium complex is the key step in the Pd-catalyzed hydrofunctionalization of 1,3-dienes, but the mechanism remains ambiguous. Commonly accepted mechanisms, such as Pd-H migratory insertion and ligand-to-ligand hydrogen transfer (LLHT), meet unfavorable thermodynamics and the requirements of coordination capacity, which may not be general for all situations. Herein, we conducted a calculation study to compare the possibility of three different pathways among several cases of Pd-catalyzed hydrofunctionalization. The results demonstrated that the π-Lewis base activation mode may be a rational pathway for the generation of the π-allylpalladium complex, in which molecular orbital (MO) and natural population analysis (NPA) indicate the nucleophilicity of 1,3-diene is activated through η2-coordination by a Pd(0) catalyst. The enantioselectivity study showed that the π-Lewis base activation mode evades ligand dissociation and maintains a rigid stereoselective environment, which provides a guarantee for the enantioselectivity of the reaction. This work suggested that the π-Lewis base activation mode was worth considering when exploring the mechanism for the Pd-catalyzed hydrofunctionalization of 1,3-diene.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311335","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
Enhanced Cytotoxicity of 10α,9β-Abiraterone Analogues Synthesized via LED Photocatalysis. LED光催化合成的10α，9β-阿比特龙类似物增强细胞毒性。
IF 3.3 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00709
Hongping Jiang, Xirong Liu, Chunling Zeng, Jie Tang, Guofang Jiang
{"title":"Enhanced Cytotoxicity of 10α,9β-Abiraterone Analogues Synthesized via LED Photocatalysis.","authors":"Hongping Jiang, Xirong Liu, Chunling Zeng, Jie Tang, Guofang Jiang","doi":"10.1021/acs.joc.5c00709","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00709","url":null,"abstract":"<p><p>Abiraterone and its analogues have been widely used in the treatment of castration-resistant prostate cancer (CRPC). However, these drugs suffer from limited bioavailability and pharmacological activity. Consequently, the modification of the abiraterone structure has become increasingly important and has attracted significant attention in recent years. This document presents 10-CH<sub>3</sub> transposable abiraterone analogues that can be synthesized through a series of 9 to 10 reaction steps, including an LED-induced photochemical conversion step to produce 10-CH<sub>3</sub>-flipped compounds with high yields. Subsequently, the newly synthesized 10-CH<sub>3</sub> transposable compounds were evaluated in cytotoxicity assays, demonstrating that compounds <b>11d</b> and <b>11f</b>, which possess 3-acetyl and 17-pyridine (or 17-benzimidazole) moieties, exhibit enhanced cytotoxicity against DU145 and HCT116 cells.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144309298","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
Acid-Enabled Dearomative Umpolung of 3-Indolylquinones toward C3-Oxygenated Benzofuro[2,3-b]indolines. 3-吲哚基醌对c3 -氧合苯并呋喃[2,3-b]吲哚的酸致脱芳研究
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00710
Wenkang Wu,Chenglong Zhu,Yongzheng Zhang,Tingting Yan,Jingyuan Yao,Guanyu Yang,Yingchao Dou
{"title":"Acid-Enabled Dearomative Umpolung of 3-Indolylquinones toward C3-Oxygenated Benzofuro[2,3-b]indolines.","authors":"Wenkang Wu,Chenglong Zhu,Yongzheng Zhang,Tingting Yan,Jingyuan Yao,Guanyu Yang,Yingchao Dou","doi":"10.1021/acs.joc.5c00710","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00710","url":null,"abstract":"We report an acid-enabled dearomative umpolung of 3-indolylquinones for the synthesis of C3-oxygenated benzofuro[2,3-b]indolines. This transformation proceeds via an intramolecular annulation, initiated by acid-facilitated formation of a dearomatized iminium intermediate. The resulting o-quinone methide motif undergoes intramolecular cyclization to generate a C3-carbocation intermediate, which is subsequently trapped by nucleophiles. A variety of alcohols (including primary, secondary, monohydric, and diols) are compatible with this reaction, providing the corresponding products in moderate to good yields. The synthetic utility of this method is demonstrated by gram-scale synthesis and derivatization studies.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"100 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311330","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
Organophotocatalyzed Radical Hydrophosphonylation of Acrylates, α,β-Unsaturated Ketones, Coumarins, Quinoxalinones, and p-Quinone Methides. 有机光催化丙烯酸酯、α、β-不饱和酮、香豆素、喹草胺酮和对醌类化合物的自由基氢膦化。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00767
Nisha Rawat,Parashuram Sharma,Seshadri Reddy Nasireddy,Anjul Vilas,Anand Singh
{"title":"Organophotocatalyzed Radical Hydrophosphonylation of Acrylates, α,β-Unsaturated Ketones, Coumarins, Quinoxalinones, and p-Quinone Methides.","authors":"Nisha Rawat,Parashuram Sharma,Seshadri Reddy Nasireddy,Anjul Vilas,Anand Singh","doi":"10.1021/acs.joc.5c00767","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00767","url":null,"abstract":"An efficient and general organophotocatalytic protocol for the hydrophosphonylation of electron-deficient alkenes is reported. Thioxanthone catalyzed generation of phosphonyl radicals from H-phosphine oxides enabled expeditious access to a range of β-phosphonylated esters, ketones, nitriles, amides, and γ-ketophosphine oxides, in excellent yields. This protocol features simple operating conditions, proceeds under mild conditions, provides access to an impressive array of diverse structural scaffolds, and exhibits broad functional group tolerance.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311649","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
Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents. C1试剂对查尔酮与吲哚酮和吲哚酮的区域发散环化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00497
Xinchi Gong,Sunewang R Wang
{"title":"Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents.","authors":"Xinchi Gong,Sunewang R Wang","doi":"10.1021/acs.joc.5c00497","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00497","url":null,"abstract":"One-pot direct regiodivergent annulations of chalcones, as exemplified by the drug metochalcone and a bioactive dichloro-substituted chalcone with a quinoline ring, to indanones and indenones are conveniently achieved with single-carbon reagent Kukhtin-Ramirez adducts. A Cs2CO3-promoted unusual selective cleavage of the cyclopropyl C-C bond distal to the strong carbonyl acceptor, further driven to completion by follow-up regiodivergent annulations via Pd(OAc)2-catalyzed Heck reaction or Cs2CO3-mediated SNAr process, is key for the success.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311265","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
The Form of the HOMA Geometric Aromaticity Index Is Universal and Allows the Design of Electronic and Magnetic Descriptors. HOMA几何芳香性指数的形式具有通用性，可用于设计电子和磁性描述符。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1021/acs.joc.5c00740
Jan Cz Dobrowolski,Sławomir Ostrowski
{"title":"The Form of the HOMA Geometric Aromaticity Index Is Universal and Allows the Design of Electronic and Magnetic Descriptors.","authors":"Jan Cz Dobrowolski,Sławomir Ostrowski","doi":"10.1021/acs.joc.5c00740","DOIUrl":"https://doi.org/10.1021/acs.joc.5c00740","url":null,"abstract":"The HOMA geometrical aromaticity index is unique. It is simple, based on observable bond distances, and can be defined using experimental or computational bond values. Moreover, its mathematical form expresses geometric similarity to the archetypal aromatic benzene. Here, we show that HOMA is simply a kind of mean of the errors squared (MSE). This is why the index is such a good measure of aromaticity. Thus, only a slight modification grounds the HOMA index on electronic or magnetic properties, producing an electronic or magnetic molecular measure expressing electronic or magnetic similarity/dissimilarity to benzene. Based on an analysis of over 70 neutral or charged carbocyclic rings, we compare the HOMA indices based on bond distances, selected electron density properties in bond or ring critical points, chemical shifts, and spin-spin coupling constants. We conclude that using electronic and magnetic variables discloses separate trends that are invisible if CC bond lengths are used. Such new HOMA indices can be used to study different facets of aromaticity and as more general molecular structure descriptors.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"43 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311329","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
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