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Cross-benzoin reaction between aliphatic aldehydes and aromatic acylals 脂肪族醛和芳香酰基之间的交叉苯并苯甲酸反应
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-08-05 DOI: 10.1016/j.tet.2025.134870
Zhaoyu Cai, Yumiko Suzuki
{"title":"Cross-benzoin reaction between aliphatic aldehydes and aromatic acylals","authors":"Zhaoyu Cai,&nbsp;Yumiko Suzuki","doi":"10.1016/j.tet.2025.134870","DOIUrl":"10.1016/j.tet.2025.134870","url":null,"abstract":"<div><div>A chemoselective cross-benzoin reaction between aliphatic aldehydes and aromatic acylals as aldehyde equivalents is presented. A triazole-based <em>N</em>-heterocyclic carbene (NHC) catalyzed the reaction between straight-chain aliphatic aldehydes and (2-halophenyl)methylene diacetates (acylals) to afford <em>α</em>-acetoxy-<em>α</em>-(2-halophenyl) ketones in 14–84 % yields. For branched aliphatic aldehydes, the NHC derived from a trimethylthiazolium with less steric bulk in the vicinity of the carbene center functioned well along with the addition of 4-(dimethylamino)pyridine (DMAP) as a cocatalyst for the gradual generation of aromatic aldehydes from the corresponding acylals.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"186 ","pages":"Article 134870"},"PeriodicalIF":2.2,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144829307","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
meta-Phenyl-cis-cinnamic acid as a strong root gravitropism inhibitor 间苯基顺式肉桂酸作为强根向倾斜抑制剂
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-30 DOI: 10.1016/j.tet.2025.134848
Mitsuru Shindo , Takeshi Nishimura , Kozue Kodama , Yuuki Furusawa , Jun Sun , Hiromi Sugiyama , Takayuki Iwata , Naoya Wasano , Arihiro Kano , Miyo Terao Morita , Yoshiharu Fujii
{"title":"meta-Phenyl-cis-cinnamic acid as a strong root gravitropism inhibitor","authors":"Mitsuru Shindo ,&nbsp;Takeshi Nishimura ,&nbsp;Kozue Kodama ,&nbsp;Yuuki Furusawa ,&nbsp;Jun Sun ,&nbsp;Hiromi Sugiyama ,&nbsp;Takayuki Iwata ,&nbsp;Naoya Wasano ,&nbsp;Arihiro Kano ,&nbsp;Miyo Terao Morita ,&nbsp;Yoshiharu Fujii","doi":"10.1016/j.tet.2025.134848","DOIUrl":"10.1016/j.tet.2025.134848","url":null,"abstract":"<div><div>In our previous studies, we identified the compound (<em>2Z,4E</em>)-5-phenylpenta-2,4-dienoic acid (BMA) as a potent gravitropic bending inhibitor, reporting it as a lead compound effective at 10 nM on <em>Lactuca</em> radicles. Based on this, we further explored derivatives of <em>cis</em>-cinnamic acid and identified mPCA, a <em>meta</em>-phenyl-<em>cis</em>-cinnamic acid that exhibits extremely potent inhibitory activity. mPCA, like BMA, effectively inhibited gravitropic bending at low concentrations without affecting root elongation or hypocotyl gravitropism in lettuce. mPCA has a simpler chemical structure than BMA and is easier to synthesize mPCA has great potential as a candidate for plant physiological studies and future agrochemical applications.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"186 ","pages":"Article 134848"},"PeriodicalIF":2.2,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144766735","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
Navigating between the worlds of mechanistic and synthetic organic chemistry 在机械化学和合成有机化学的世界之间导航
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-30 DOI: 10.1016/j.tet.2025.134862
Eric N. Jacobsen
{"title":"Navigating between the worlds of mechanistic and synthetic organic chemistry","authors":"Eric N. Jacobsen","doi":"10.1016/j.tet.2025.134862","DOIUrl":"10.1016/j.tet.2025.134862","url":null,"abstract":"","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"186 ","pages":"Article 134862"},"PeriodicalIF":2.2,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144829309","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
Transition-metal-free decarboxylative acylation of sulfoximines: An efficient route to N-(ortho-aminobenzoyl)sulfoximines 亚砜亚胺的无过渡金属脱羧酰化：N-（邻氨基苯甲酰）亚砜亚胺的有效途径
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-28 DOI: 10.1016/j.tet.2025.134867
Meng Ding, Qingle Zeng
{"title":"Transition-metal-free decarboxylative acylation of sulfoximines: An efficient route to N-(ortho-aminobenzoyl)sulfoximines","authors":"Meng Ding,&nbsp;Qingle Zeng","doi":"10.1016/j.tet.2025.134867","DOIUrl":"10.1016/j.tet.2025.134867","url":null,"abstract":"<div><div>A transition-metal-free decarboxylative acylation strategy for constructing C–N bonds in sulfoximines and isatoic anhydrides is reported. This method enables the synthesis of 26 N-(ortho-aminobenzoyl)sulfoximines in 52 %–82 % yields, featuring gram-scale feasibility and versatile post-modifications for potential bioactive derivatives.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134867"},"PeriodicalIF":2.2,"publicationDate":"2025-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144724959","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
Ball-milling multicomponent reactions for diverse organic transformations 不同有机转化的球磨多组分反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-26 DOI: 10.1016/j.tet.2025.134863
Hossein Yazdani , Seyyed Emad Hooshmand , Ahmed Al-Harrasi
{"title":"Ball-milling multicomponent reactions for diverse organic transformations","authors":"Hossein Yazdani ,&nbsp;Seyyed Emad Hooshmand ,&nbsp;Ahmed Al-Harrasi","doi":"10.1016/j.tet.2025.134863","DOIUrl":"10.1016/j.tet.2025.134863","url":null,"abstract":"<div><div>Over the past two decades, the search for environmentally friendly, novel, and cleaner synthetic methods has been extended. Owing to their unique reactivity, practicality, and efficiency, the ball-milling processing of solids has developed into a powerful tool for transforming, screening, and synthesizing various classes of molecules and materials within the strongly invoked green and sustainable chemistry paradigm. This green and sustainable technique has significant advantages encompassing improved yields, safety and selectivity, use of insoluble starting materials, moisture- and air-sensitivity precaution-free setup, telescoping of reactions, reduced operational reaction times, new types of reactivity, and reduced use of organic solvents. On the other hand, multicomponent reactions (MCRs) lead to the expeditious preparation of novel complex molecules, active pharmaceutical ingredients (APIs), and biologically active molecules with a low E-factor and atom economy, as well as high efficiency. They can be carried out in one-pot operations using three or more reactants. This review intends to focus on MCRs under ball-milling processing. It covers the most recent developments in the newly established area of ball-milling synthesis of MCRs. Future opportunities and challenges will also be elaborated.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134863"},"PeriodicalIF":2.1,"publicationDate":"2025-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144713177","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
Synthesis of phosphoryl imidazo[1,2-a]pyridines enabled by a molecular I2 catalyzed Gröbcke-Blackburn-Bienaymé reaction 用分子I2催化Gröbcke-Blackburn-Bienaymé反应合成磷酰咪唑[1,2-a]吡啶
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-25 DOI: 10.1016/j.tet.2025.134864
Wen Qin , Lingmeng Xie , Jingru Zou , Xingang Xie , Xing Huo
{"title":"Synthesis of phosphoryl imidazo[1,2-a]pyridines enabled by a molecular I2 catalyzed Gröbcke-Blackburn-Bienaymé reaction","authors":"Wen Qin ,&nbsp;Lingmeng Xie ,&nbsp;Jingru Zou ,&nbsp;Xingang Xie ,&nbsp;Xing Huo","doi":"10.1016/j.tet.2025.134864","DOIUrl":"10.1016/j.tet.2025.134864","url":null,"abstract":"<div><div>Phosphoryl-substituted imidazo[1,2-<em>a</em>]pyridines were efficiently synthesized via iodine-catalyzed Groebke-Blackburn-Bienaymé (GBB) three-component reaction, using phosphonate/phosphine oxide-substituted aldehydes, 2-aminopyridines and isocyanides. This reaction proceeds in green solvent ethanol, with yields up to 89 %, and advantages of mild conditions, broad compatibility and high atom economy. Derivative transformations and multigram scalability highlight its utility.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134864"},"PeriodicalIF":2.1,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144713179","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
Molecular diversity of three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones 烷基异氰酸酯、二烷基丁-2-炔酸酯和2-芳基-1,3-茚二酮三组分反应的分子多样性
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-25 DOI: 10.1016/j.tet.2025.134853
Shao-Cong Zhan, Li Huang, Jing Sun, Chao-Guo Yan
{"title":"Molecular diversity of three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones","authors":"Shao-Cong Zhan,&nbsp;Li Huang,&nbsp;Jing Sun,&nbsp;Chao-Guo Yan","doi":"10.1016/j.tet.2025.134853","DOIUrl":"10.1016/j.tet.2025.134853","url":null,"abstract":"<div><div>The three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones showed very interesting molecular diversity. The three-component reaction in refluxing acetonitrile afforded functionalized spiro[furan-2,1′-indene] derivatives. On the other hand, the three-component reaction in refluxing ethanol gave functionalized cyclopenta[<em>b</em>]naphthalene derivatives. In addition, the similar three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5-arylidene<em>-N,N′</em>-dimethylbarbituric acids resulted in functionalized diazaspiro[4.5]deca-1,3-diene-1,2-dicarboxylates in satisfactory yields. A plausible reaction mechanism including <em>in situ</em> of Huisgen's 1,4-dipole, and sequential annulation reaction was proposed to explain the formation of the different polycyclic compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134853"},"PeriodicalIF":2.2,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144721122","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
Solvent-controlled selective synthesis of quinazolinones and 2-arylquinazolinones via copper-catalyzed [5 + 1] annulation 铜催化[5 + 1]环化溶剂控制选择性合成喹唑啉酮和2-芳基喹唑啉酮
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-07-24 DOI: 10.1016/j.tet.2025.134858
Min Wang, Kexin Li, Jiaao Xue, Kewei Hu, Duoluo Guo, Qun Cai
{"title":"Solvent-controlled selective synthesis of quinazolinones and 2-arylquinazolinones via copper-catalyzed [5 + 1] annulation","authors":"Min Wang,&nbsp;Kexin Li,&nbsp;Jiaao Xue,&nbsp;Kewei Hu,&nbsp;Duoluo Guo,&nbsp;Qun Cai","doi":"10.1016/j.tet.2025.134858","DOIUrl":"10.1016/j.tet.2025.134858","url":null,"abstract":"<div><div>A copper-catalyzed cyclization for the selective synthesis of quinazolinones and 2-arylquinazolinones depending on solvent control has been established. <em>o</em>-Aminobenzamide is employed as an unprecedented C1 source involving in the [5 + 1] annulation to form 2-arylquinazolinones via double C–N bonds cleavage in Cu/DMSO system. While adjusting the solvent to MeOH achieves quinazolinones in high yields. Furthermore, the gram-scalable assembly and late-stage transformations of quinazolines demonstrate significant synthetic applications of this method.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134858"},"PeriodicalIF":2.1,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144713178","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
Electron pull-push modulation: Substrate controlled regioselectivity switch in 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with chalcones 电子推拉调制：底物控制区域选择性开关在1,3-偶极环加成的isatin衍生亚甲基酰与查尔酮
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-24 DOI: 10.1016/j.tet.2025.134865
Shubham Dashora , Anirban Chowdhury , Dhruvisha Kiritbhai Patel , Uma Mahesh Addala , Srinu Tothadi , Keshav Lalit Ameta
{"title":"Electron pull-push modulation: Substrate controlled regioselectivity switch in 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with chalcones","authors":"Shubham Dashora ,&nbsp;Anirban Chowdhury ,&nbsp;Dhruvisha Kiritbhai Patel ,&nbsp;Uma Mahesh Addala ,&nbsp;Srinu Tothadi ,&nbsp;Keshav Lalit Ameta","doi":"10.1016/j.tet.2025.134865","DOIUrl":"10.1016/j.tet.2025.134865","url":null,"abstract":"<div><div>A switch in regioselectivity has been achieved by modulating electron pull and push during the synthesis of spiropyrrolidine-oxindole analogs through 1,3-dipolar cycloaddition of isatin derived in-situ generated azomethine ylides with chalcones. Electron-withdrawing groups on ketone termini, along with neutral or electron-withdrawing groups on aldehyde termini, favored β-attack. In contrast, electron-donating groups on aldehyde termini switch the selectivity to α-attack. Structures of regioisomers have been determined by NMR, HRMS and SC-XRD.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"186 ","pages":"Article 134865"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144766736","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
Two new diterpenoic acids isolated from Carpesium divaricatum exhibited growth-inhibitory activity against epithelial–mesenchymal transition-induced cells 从金盏花中分离的两种新的二萜酸对上皮间充质转化诱导的细胞具有生长抑制活性
IF 2.2 3区 化学
Tetrahedron Pub Date : 2025-07-24 DOI: 10.1016/j.tet.2025.134854
Hirotaka Matsuo , Hitomi Kawakami , Noriaki Kawano , Hiroyuki Fuchino , Kayo Yoshimatsu
{"title":"Two new diterpenoic acids isolated from Carpesium divaricatum exhibited growth-inhibitory activity against epithelial–mesenchymal transition-induced cells","authors":"Hirotaka Matsuo ,&nbsp;Hitomi Kawakami ,&nbsp;Noriaki Kawano ,&nbsp;Hiroyuki Fuchino ,&nbsp;Kayo Yoshimatsu","doi":"10.1016/j.tet.2025.134854","DOIUrl":"10.1016/j.tet.2025.134854","url":null,"abstract":"<div><div>Epithelial–mesenchymal transition (EMT) has recently been reported to be associated with cancer invasion, metastasis, and resistance. Novel cancer treatment strategies should focus on controlling EMT. In a previous study, we established a screening method for growth inhibitors in EMT-induced (EMTed) Madin–Darby canine kidney (MDCK) cells. During screening, a methanolic extract of <em>Carpesium divaricatum</em> showed growth-inhibitory activity against EMTed MDCK cells. After bioguided extract purification, two new diterpenoids, designated divariterpenoic acids A (<strong>1</strong>) and B (<strong>2</strong>), were isolated from the extract, along with two known compounds, 2α,5-epoxy-5,10-dihydroxy-6α-angeloyloxy-9-isobutyloxy-germacran-8,12-olide (<strong>3</strong>) and divaricin B (<strong>4</strong>). The structures of new diterpenoids <strong>1</strong> and <strong>2</strong> were elucidated by 1D and 2D-NMR and HRESI-MS data. Compounds <strong>1</strong>–<strong>4</strong> displayed growth-inhibitory activity on EMTed MDCK cells, with compound <strong>4</strong> showing the strongest activity. Furthermore, the growth-inhibitory activities of compounds <strong>2</strong>–<strong>4</strong> on two EMTed human cancer cell lines, A549 and SAS, were evaluated. Compound <strong>2</strong> inhibited the growth of EMTed SAS cells. Compounds <strong>3</strong> and <strong>4</strong> inhibited the growth of EMTed SAS and A549 cells.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134854"},"PeriodicalIF":2.2,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144721233","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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