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Design, synthesis, and evaluation of petrosiol E derivatives on neuronal progenitors differentiation 石油E衍生物对神经祖细胞分化的设计、合成和评价
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-11-14 DOI: 10.1016/j.tet.2025.135060
Yuanfang Liu , Ruiying Pan , Xinni Xie , Jun Liu , Yuguo Du
{"title":"Design, synthesis, and evaluation of petrosiol E derivatives on neuronal progenitors differentiation","authors":"Yuanfang Liu ,&nbsp;Ruiying Pan ,&nbsp;Xinni Xie ,&nbsp;Jun Liu ,&nbsp;Yuguo Du","doi":"10.1016/j.tet.2025.135060","DOIUrl":"10.1016/j.tet.2025.135060","url":null,"abstract":"<div><div>A series of novel petrosiol E derivatives were synthesized by divergent strategies starting from readily available <span>d</span>-xylose as the chiral template. The pro-differentiating capacities of these derivatives were evaluated using a differentiation model of rat neuron-like PC12 cells and several derivatives exhibited moderate to significant pro-differentiating capacities. Our study demonstrated that the pro-differentiating capacities of these derivatives were very sensitive to modifications in the side chains, suggesting that the conjugated diyne skeleton and terminal alkyl residue might play important roles in the neuronal differentiation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135060"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145577159","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Asymmetric synthesis of chiral 4,5,6-trisubstituted-3,4-dihydropyrimidinethiones catalyzed by chiral Brønsted acid 手性Brønsted酸催化不对称合成4,5,6-三取代-3,4-二氢嘧啶硫酮
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-27 DOI: 10.1016/j.tet.2025.134999
Lingkai Kong, Zhe Li, Chunzhi Ju, Peng Wang, Guangliang Zhang, Suoqin Zhang
{"title":"Asymmetric synthesis of chiral 4,5,6-trisubstituted-3,4-dihydropyrimidinethiones catalyzed by chiral Brønsted acid","authors":"Lingkai Kong,&nbsp;Zhe Li,&nbsp;Chunzhi Ju,&nbsp;Peng Wang,&nbsp;Guangliang Zhang,&nbsp;Suoqin Zhang","doi":"10.1016/j.tet.2025.134999","DOIUrl":"10.1016/j.tet.2025.134999","url":null,"abstract":"<div><div>The low steric hindrance of small-substituent 2,4-diketones presents a significant challenge for effective asymmetric induction.An efficient and highly enantioselective catalytic system was developed for the Biginelli reaction to access chiral 4,5,6-trisubstituted-3,4-dihydropyrimidinethiones. Through catalyst screening, chiral imidodiphosphoric acid was found to outperform conventional chiral phosphoric acids. Under the optimized conditions, up to 99 % ee and 52–92 % isolated yields were achieved. This method offers a valuable strategy for the asymmetric synthesis of bioactive pyrimidine derivatives with potential pharmaceutical applicatioins.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 134999"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145384501","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Lewis base catalyzed N-selective allylation of sufenamides with Morita–Baylis–Hillman carbonates 路易斯碱催化磺酰胺与森田-贝利斯-希尔曼碳酸盐的n -选择性烯丙化反应
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-11-12 DOI: 10.1016/j.tet.2025.135057
Jiahong Chen, Yuanyuan Huang, Nan Wang, You Zi
{"title":"Lewis base catalyzed N-selective allylation of sufenamides with Morita–Baylis–Hillman carbonates","authors":"Jiahong Chen,&nbsp;Yuanyuan Huang,&nbsp;Nan Wang,&nbsp;You Zi","doi":"10.1016/j.tet.2025.135057","DOIUrl":"10.1016/j.tet.2025.135057","url":null,"abstract":"<div><div>A practical and N-selective allylation of sulfenamides using Morita-Baylis-Hillman carbonates under Lewis base catalysis is reported. It features broad substrate scope, high chemoselectivity, and tolerance to various functional groups, affording diverse N-allylated sulfenamides in good to excellent yields. Gram-scale experiments confirm its scalability, facilitating the synthesis of bioactive molecules and expanding the utility of sulfenamide chemistry.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135057"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526717","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Photoinduced cyclopropanation of olefins via silicoborate-mediated radical transfer 通过硅酸盐介导的自由基转移光诱导烯烃环丙烷化
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-28 DOI: 10.1016/j.tet.2025.135027
Zhen-Ye Wu , Jiang-Hong Liu , Qing Liu , Li Hai , Zhong-Zhen Yang , Yong Wu
{"title":"Photoinduced cyclopropanation of olefins via silicoborate-mediated radical transfer","authors":"Zhen-Ye Wu ,&nbsp;Jiang-Hong Liu ,&nbsp;Qing Liu ,&nbsp;Li Hai ,&nbsp;Zhong-Zhen Yang ,&nbsp;Yong Wu","doi":"10.1016/j.tet.2025.135027","DOIUrl":"10.1016/j.tet.2025.135027","url":null,"abstract":"<div><div>Under visible-light irradiation, a metal-free photocatalytic system enables the generation of reactive silicon-centered radicals from a silicate reagent. The radicals undergo efficient addition to olefins, followed by polarity inversion, elimination of the leaving group, and strain-driven cyclization to afford cyclopropane-functionalized silicon products. Notably, this protocol avoids transition-metal catalysts and exhibits broad functional group tolerance. The reaction provides a sustainable strategy for constructing strained carbocycles under mild conditions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135027"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145415049","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Pd-catalyzed site-selective arene ortho C–H chlorination of 4-aryl-pyrrolo[2,3-d]pyrimidines with para- toluenesulfonylchloride pd催化4-芳基吡咯[2,3-d]嘧啶与对甲苯磺酰氯的位置选择性芳烃邻位氯化反应
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-18 DOI: 10.1016/j.tet.2025.135000
Junyang Tang , Yaorong Liu , Baojie Qiu , Chun He , Xingxian Zhang
{"title":"Pd-catalyzed site-selective arene ortho C–H chlorination of 4-aryl-pyrrolo[2,3-d]pyrimidines with para- toluenesulfonylchloride","authors":"Junyang Tang ,&nbsp;Yaorong Liu ,&nbsp;Baojie Qiu ,&nbsp;Chun He ,&nbsp;Xingxian Zhang","doi":"10.1016/j.tet.2025.135000","DOIUrl":"10.1016/j.tet.2025.135000","url":null,"abstract":"<div><div>A palladium-catalyzed arene <em>ortho</em> C–H chlorination of 4-aryl-pyrrolo[2,3-<em>d</em>]pyrimidines has been developed using inexpensive <em>p</em>-toluenesulfonyl chloride (TsCl) as a practical chlorine source. This transformation endows facile fabrication of C–Cl bond with high regioselectivity and wide functional group tolerance exploiting directing properties of pyrimidinic nitrogen on pharmacodynamic 7-deazapurines. The synthetic utility of this protocol is demonstrated through gram-scale synthesis and diverse late-stage functionalization.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135000"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145415047","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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(OAc)2/K2S2O8 promoted aminooximation of β,γ-unsaturated hydrazones to access pyrazoline substituted oxime ethers Cu(OAc)2/K2S2O8促进β，γ-不饱和腙氨基肟化以获得吡唑啉取代肟醚
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-31 DOI: 10.1016/j.tet.2025.135036
Quanlin Wu , Can Yang , Xinying Man , Xin Li , Quansen Wu , Yijing Zhang , Dongfang Jiang , Zhenjie Qi
{"title":"Cu(OAc)2/K2S2O8 promoted aminooximation of β,γ-unsaturated hydrazones to access pyrazoline substituted oxime ethers","authors":"Quanlin Wu ,&nbsp;Can Yang ,&nbsp;Xinying Man ,&nbsp;Xin Li ,&nbsp;Quansen Wu ,&nbsp;Yijing Zhang ,&nbsp;Dongfang Jiang ,&nbsp;Zhenjie Qi","doi":"10.1016/j.tet.2025.135036","DOIUrl":"10.1016/j.tet.2025.135036","url":null,"abstract":"<div><div>A novel Cu(OAc)<sub>2</sub>-catalyzed tandem cyclization/addition strategy has been developed for the synthesis of pyrazoline substituted oxime ethers from <em>β</em>,<em>γ</em>-unsaturated hydrazones and oximes using K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> as an oxidant and NaHCO<sub>3</sub> as a base has been achieved. The reaction demonstrates broad substrate scope, tolerating aryl, heteroaryl, alkyl, and sulfonyl substituents on both hydrazones and oximes, and provides the products in up to 78 % yield. Mechanistic studies suggest the involvement of both energy transfer and single electron transfer processes in accomplishing the radical 5-<em>exo</em>-trig cyclization to the C<img>N bond. Furthermore, scale-up experiment was also enabled.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135036"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475158","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 asymmetric arylation of α-2-nitrophenylsulfenylimino acetamide 钯催化α-2-硝基苯基磺酰氨基乙酰胺的不对称芳基化反应
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-11-03 DOI: 10.1016/j.tet.2025.135041
Tsubasa Inokuma , Koki Fukuhara , Masayuki Sugano , Maki Miyamoto , Takatoshi Someno , Ken-ichi Yamada
{"title":"Palladium-catalyzed asymmetric arylation of α-2-nitrophenylsulfenylimino acetamide","authors":"Tsubasa Inokuma ,&nbsp;Koki Fukuhara ,&nbsp;Masayuki Sugano ,&nbsp;Maki Miyamoto ,&nbsp;Takatoshi Someno ,&nbsp;Ken-ichi Yamada","doi":"10.1016/j.tet.2025.135041","DOIUrl":"10.1016/j.tet.2025.135041","url":null,"abstract":"<div><div>Palladium-catalyzed asymmetric arylation of α-2-nitrophenylsulfenylimino acetamide has been developed for the synthesis of arylglycine-containing peptides. The addition of a weakly coordinating anion is essential for the progress of this reaction. The protecting group of the arylated product is readily removed, and the resulting free amine undergoes N-terminal extension without racemization.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135041"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526713","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 synergistic photoredox/palladium catalysis for decarboxylative benzoylation of aryl pyridines: Efficient access to pyridine-substituted aryl ketones at ambient temperature 可见光诱导的芳基吡啶脱羧苯甲酰化的协同光氧化还原/钯催化：在室温下有效地获得吡啶取代的芳基酮
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-31 DOI: 10.1016/j.tet.2025.135037
Feifei Wen , Xuyang Zhao , Xueqin Song , Huan Ma , Chengwang Wang , Yu Zhang , Pan Xie
{"title":"Visible light-induced synergistic photoredox/palladium catalysis for decarboxylative benzoylation of aryl pyridines: Efficient access to pyridine-substituted aryl ketones at ambient temperature","authors":"Feifei Wen ,&nbsp;Xuyang Zhao ,&nbsp;Xueqin Song ,&nbsp;Huan Ma ,&nbsp;Chengwang Wang ,&nbsp;Yu Zhang ,&nbsp;Pan Xie","doi":"10.1016/j.tet.2025.135037","DOIUrl":"10.1016/j.tet.2025.135037","url":null,"abstract":"<div><div>A novel synergistic photoredox/palladium catalytic system has been developed for the visible light-induced decarboxylative benzoylation of arylpyridines using <em>α</em>-oxocarboxylic acids. This method proceeds efficiently at ambient temperature under aerobic conditions, employing Eosin Y as the photocatalyst, a Pd(II) complex as the transition metal catalyst, and K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> as the oxidant. A broad substrate scope, encompassing electron-donating and electron-withdrawing groups as well as diverse heterocyclic acids, afforded the corresponding benzoyl-substituted heteroarenes in moderate to good yields. This protocol offers an economical, mild, and sustainable strategy for the synthesis of valuable aromatic ketones, thereby advancing the field of dual photoredox/palladium catalysis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135037"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145475098","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Electrochemically driven benzoazepine-tethered acrylate synthesis 电化学驱动苯并氮卓系链丙烯酸酯合成
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-30 DOI: 10.1016/j.tet.2025.135033
Musarrat Fatma, Faiz Ahmed Khan
{"title":"Electrochemically driven benzoazepine-tethered acrylate synthesis","authors":"Musarrat Fatma,&nbsp;Faiz Ahmed Khan","doi":"10.1016/j.tet.2025.135033","DOIUrl":"10.1016/j.tet.2025.135033","url":null,"abstract":"<div><div>Herein, we present an intramolecular palladium catalyzed cascade electrochemical reaction in an undivided cell at room temperature to afford benzoazepine-tethered acrylate derivatives. The reaction pathway is proposed to occur initially <em>via</em> selective iodination followed by 7-<em>endo-</em>dig selective cyclization followed by Heck coupling at room temperature using palladium catalyst. The reaction features broad substrate scope with good yields under mild condition and effectively underlines the role of expanding palladium assisted electrochemical transformation.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135033"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145415048","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Bis-arylation of phenylene-bridged bis-azolium salts and tetra-arylation of bis-azoles to access symmetrical and unsymmetrical CCC-aNHC pincer ligand precursors 苯基桥接双唑盐的双芳基化和双唑的四芳基化得到对称和不对称的cc - anhc钳形配体前体
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-11-07 DOI: 10.1016/j.tet.2025.135045
Alan C. Cecil, Evans Fosu, Bruno Donnadieu, T. Keith Hollis
{"title":"Bis-arylation of phenylene-bridged bis-azolium salts and tetra-arylation of bis-azoles to access symmetrical and unsymmetrical CCC-aNHC pincer ligand precursors","authors":"Alan C. Cecil,&nbsp;Evans Fosu,&nbsp;Bruno Donnadieu,&nbsp;T. Keith Hollis","doi":"10.1016/j.tet.2025.135045","DOIUrl":"10.1016/j.tet.2025.135045","url":null,"abstract":"<div><div>Copper-mediated methodologies for the arylation of bis-azolium salts and bis-azoles are efficient pathways to access symmetrical and unsymmetrical <em>N</em>-heterocyclic carbene precursors. The arylation of bis-azolium salts with various aryl halides was achieved in moderate yields to furnish numerous C2-arylated bis-azolium salts. Access of C2-arylated bis-azolium salts from bis-azoles was also achieved in a single pot domino reaction via the use of iodonium salts as embedded electrophiles. The latter methodology utilizes the aryl iodide byproduct from the N-arylation step for the C–H activation step to mitigate waste and the need to recycle. We also demonstrated the use of these azolium salts in metalation and found success in obtaining metal complexes containing abnormal <em>N</em>-heterocyclic carbenes.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"190 ","pages":"Article 135045"},"PeriodicalIF":2.2,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145526712","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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