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Highly Active Oligoethylene Glycol Pleuromutilins via Systematic Linker Synthesis/One-Pot Attachment and a Microscale Solubility Method
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02683
Logan M. Breiner, Roman P. Slowinski, Andrew N. Lowell
{"title":"Highly Active Oligoethylene Glycol Pleuromutilins via Systematic Linker Synthesis/One-Pot Attachment and a Microscale Solubility Method","authors":"Logan M. Breiner, Roman P. Slowinski, Andrew N. Lowell","doi":"10.1021/acs.joc.4c02683","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02683","url":null,"abstract":"The semisynthetic derivatization of natural products is crucial for their continued development as antibiotics. While commercial pleuromutilin derivatives depend on amines for solubility, we demonstrate the high activity and solubility of oligoethylene glycol-substituted pleuromutilins achieved via a one-pot deprotection/attachment approach using thiolates protected as thioesters. The bifunctional linker synthesis is versatile and can be broadly applied to other chemistries. Antibacterial assays revealed this simple glycolate modification enhanced inhibition 4–8-fold relative to that of pleuromutilin. A new microscale solubility method is also introduced.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849695","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
One-Step Construction of 2-Methylquinazolin-4(3H)-ones Using Solid Calcium Carbide as an Alternative to Gaseous Acetylene
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02341
Botao Wang, Zhiqiang Wang, Xinjie You, Zheng Li, Jinhui Yang
{"title":"One-Step Construction of 2-Methylquinazolin-4(3H)-ones Using Solid Calcium Carbide as an Alternative to Gaseous Acetylene","authors":"Botao Wang, Zhiqiang Wang, Xinjie You, Zheng Li, Jinhui Yang","doi":"10.1021/acs.joc.4c02341","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02341","url":null,"abstract":"2-Methylquinazolin-4(3<i>H</i>)-ones were efficiently constructed using solid calcium carbide as an alkyne source, 2-aminobenzamides or 2-aminobenzohydrazides as substrates, and <i>p</i>-tolylsulfonyl azide as a mediator through simultaneous formation of two C–N bonds in one step. The salient features of this protocol are the use of an inexpensive, abundant and easy-to-use alkyne source as a substitute for flammable and explosive gaseous acetylene, low-cost catalyst, wide substrate scope, satisfactory yield, and simple manipulation. This method can also be extended to gram scale.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841795","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
Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02530
Yingchun Ma, Ping Yu, Ruoyu Qin, Run He, Li Zeng, Lou Shi, Shaoguang Sun, Deqiang Liang
{"title":"Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes","authors":"Yingchun Ma, Ping Yu, Ruoyu Qin, Run He, Li Zeng, Lou Shi, Shaoguang Sun, Deqiang Liang","doi":"10.1021/acs.joc.4c02530","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02530","url":null,"abstract":"We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range of unactivated alkenes, using the inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) to produce a diverse array of heterocycles containing sulfonyl and thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- and transition-metal-free, with a broad scope of substrates. Preliminary mechanistic studies suggest that the reaction involves a combination of electrolysis and the reductive quenching photocatalytic cycle of TPPT.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"62 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849693","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
Sc(OTf)3-Catalyzed Precise Construction of Medium-Sized [4.2.1]-Oxabridged Scaffolds
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02657
Dong-Sheng Ji, Chenxing Zhou, Xudong Wang, Xiazhen Bao, Yong Yuan, Congde Huo
{"title":"Sc(OTf)3-Catalyzed Precise Construction of Medium-Sized [4.2.1]-Oxabridged Scaffolds","authors":"Dong-Sheng Ji, Chenxing Zhou, Xudong Wang, Xiazhen Bao, Yong Yuan, Congde Huo","doi":"10.1021/acs.joc.4c02657","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02657","url":null,"abstract":"In this study, the readily available and inexpensive Sc(OTf)<sub>3</sub> was utilized to activate ortho-benzoyl diazo compounds to in situ generate highly reactive cyclic 1,3-dipoles, which underwent a regioselective [4 + 3] cycloaddition with dioxopyrrolidines, yielding the [4.2.1]-oxabridged scaffolds bearing multiple contiguous quaternary carbon centers with high diastereoselectivities. The method not only exhibited significant economic and operational advantages but also demonstrated practical value through gram-scale synthesis and derivatization experiments.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"93 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849825","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
Synthesis of 2-Phosphonylated C3 Spirocyclic Indolines via a Dearomatization–Spirocyclization–Nucleophilic Addition Tandem Approach of Indolyl-ynones with Phosphine Oxides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02364
Jiongjiong Duan, Yi Cao, Huanping Xie, Yongqi Yu, Heyun Sheng, Weiguang Kong, Ting Li
{"title":"Synthesis of 2-Phosphonylated C3 Spirocyclic Indolines via a Dearomatization–Spirocyclization–Nucleophilic Addition Tandem Approach of Indolyl-ynones with Phosphine Oxides","authors":"Jiongjiong Duan, Yi Cao, Huanping Xie, Yongqi Yu, Heyun Sheng, Weiguang Kong, Ting Li","doi":"10.1021/acs.joc.4c02364","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02364","url":null,"abstract":"Due to its unique three-dimensional (3D) configuration and great application potential in medicinal chemistry and synthetic community, chemists have been pursuing concise and efficient methods to synthesize C3 spirocyclic indoline derivatives. In this work, a dearomatization–spirocyclization–nucleophilic addition tandem approach was developed to realize the synthesis of 2-phosphonylated C3 spirocyclic indolines with indolyl-ynones and phosphine oxides as reactants; mild conditions, broad substrate scope, and good yields are characteristics of this transformation.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841796","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
Nickel Photoredox/Dual-Catalyzed Transfer Semi-Hydrogenation of Alkynes via Aminoalkyl Nickel Species
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02071
Kento Nakamura, Kokona Odama, Tomoya Fukuta, Yoshihiro Sato
{"title":"Nickel Photoredox/Dual-Catalyzed Transfer Semi-Hydrogenation of Alkynes via Aminoalkyl Nickel Species","authors":"Kento Nakamura, Kokona Odama, Tomoya Fukuta, Yoshihiro Sato","doi":"10.1021/acs.joc.4c02071","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02071","url":null,"abstract":"Using amines in catalytic transfer hydrogenation (TH) is challenging, despite their potential availability as a hydrogen source. Here, we describe a photoredox/nickel-catalyzed TH of alkyne through an intermediary aminoalkyl Ni species. This reaction successfully provided functionalized (<i>Z</i>)-alkenes, such as (homo)allyl ethers, alcohols, and amides (<i>Z</i>/<i>E</i> = up to &gt;99:1), and the reaction thus bypasses a limitation of substrate scope in TH using amine and a Lindlar catalyst. Mechanistic studies revealed that the aminoalkyl Ni species plausibly participates in two catalyst regeneration paths: (1) β-hydride elimination followed by reductive elimination and (2) protodemetalation from alkenyl Ni<sup>I</sup>.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841794","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
Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02679
Feifei Jin, Qing Wu, Shuaijie Wu, Huiwen Dong, Yanru He, Jing Sun, Chao-Guo Yan, Wenbo Li, Lei Wang
{"title":"Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs","authors":"Feifei Jin, Qing Wu, Shuaijie Wu, Huiwen Dong, Yanru He, Jing Sun, Chao-Guo Yan, Wenbo Li, Lei Wang","doi":"10.1021/acs.joc.4c02679","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02679","url":null,"abstract":"A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841797","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
Sustainable Synthesis of Substituted 1,3,5-Triazines by [ONO]-Pincer-Supported Nickel(II) Complexes via an Acceptorless Dehydrogenative Coupling Strategy
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1021/acs.joc.4c02118
Anandaraj Pennamuthiriyan, Ramesh Rengan, Jan Grzegorz Malecki
{"title":"Sustainable Synthesis of Substituted 1,3,5-Triazines by [ONO]-Pincer-Supported Nickel(II) Complexes via an Acceptorless Dehydrogenative Coupling Strategy","authors":"Anandaraj Pennamuthiriyan, Ramesh Rengan, Jan Grzegorz Malecki","doi":"10.1021/acs.joc.4c02118","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02118","url":null,"abstract":"A facile, cost-effective, and sustainable synthesis of substituted triazines from primary alcohols by newly synthesized nickel pincer-type complexes (<b>1</b>–<b>3</b>) has been described. Herein, we report the synthesis of a set of three well-defined Ni(II) O^N^O pincer-type complexes, structurally characterized by analytical, spectral, and X-ray diffraction techniques. Further, the nickel complexes are explored as efficient catalysts (4 mol %) for the construction of 2,4,6-substituted 1,3,5-triazines from readily available alcohols via an acceptorless dehydrogenative coupling (ADC) strategy. A wide range of substituted triazine derivatives (33 examples) has been synthesized from the coupling of alcohols and benzamidine/guanidine hydrochloride with a maximum isolated yield of 92% under mild conditions, with eco-friendly H<sub>2</sub>O and H<sub>2</sub> gas as the only byproducts. A plausible mechanism has been proposed based on a sequence of control experiments. Interestingly, the short synthesis of the antiulcer drug irsogladine and the large-scale synthesis of 2,4-diphenyl-6-(<i>p</i>-tolyl)-1,3,5-triazine highlight the convenience of the current methodology.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"62 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849702","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
Copper-Catalyzed Domino Phosphorylation/Cyclization of ortho-Alkynylketones for Accessing Phosphorylated 1H-Isochromenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02239
Xiao-Hong Wei, Xuan Liu, Xiao-Hong Wang, Ya-Wen Xue, Xiao-Jun Yang, Shang-Dong Yang
{"title":"Copper-Catalyzed Domino Phosphorylation/Cyclization of ortho-Alkynylketones for Accessing Phosphorylated 1H-Isochromenes","authors":"Xiao-Hong Wei, Xuan Liu, Xiao-Hong Wang, Ya-Wen Xue, Xiao-Jun Yang, Shang-Dong Yang","doi":"10.1021/acs.joc.4c02239","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02239","url":null,"abstract":"An effective and economical copper-catalyzed approach for the synthesis of phosphorylated 1<i>H</i>-isochromenes is reported. This method is the first example of focus on ketone phosphonylation to establish a C–P bond and 6-<i>endo</i>-<i>dig</i> cyclization to construct a C–O bond between aryl- and alkyl-substituted alkynylketones and H-phosphinate esters, H-phosphites, and H-phosphine oxides, resulting in chemo- and regioselective phosphorylated 1<i>H</i>-isochromenes with moderate to excellent yields under smooth reaction conditions.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841799","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
Palladium-Catalyzed Annulation Reaction of Bay-Iodobiphenyls with Maleimides to Access 9,10-Phenanthrenedicarboximides
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1021/acs.joc.4c02359
Xin-Yuan Long, Na Huang, Cheng-Rong Cui, Yingbo Shi, Chun Feng, Bi-Qin Wang, Shilin Zhang, Shi-Kai Xiang
{"title":"Palladium-Catalyzed Annulation Reaction of Bay-Iodobiphenyls with Maleimides to Access 9,10-Phenanthrenedicarboximides","authors":"Xin-Yuan Long, Na Huang, Cheng-Rong Cui, Yingbo Shi, Chun Feng, Bi-Qin Wang, Shilin Zhang, Shi-Kai Xiang","doi":"10.1021/acs.joc.4c02359","DOIUrl":"https://doi.org/10.1021/acs.joc.4c02359","url":null,"abstract":"A palladium-catalyzed annulation reaction of bay-iodobiphenyls with maleimides was developed. This approach allows for the efficient synthesis of a variety of 9,10-phenanthrenedicarboximides, particularly polyalkoxy-substituted 9,10-phenanthrenedicarboximides with potential liquid-crystalline properties. Research findings indicate that the resulting product, <i>N</i>-hexyl-2,3,6,7-tetrakis(hexyloxy)-9,10-phenanthrenedicarboximide, exhibits promising, good liquid-crystalline properties.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"145 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841802","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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