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Direct C–H aminocarbonylation of quinone derivatives with isocyanides under transition-metal free conditions 醌类衍生物与异氰酸酯在无过渡金属条件下的直接C-H氨基羰基化反应
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-14 DOI: 10.1016/j.tet.2025.134779
Yingjie Zhang, Yuxuan Zhao, Jiankang Ou, Zeguo Fang, Qian Zhang, Dong Li
{"title":"Direct C–H aminocarbonylation of quinone derivatives with isocyanides under transition-metal free conditions","authors":"Yingjie Zhang,&nbsp;Yuxuan Zhao,&nbsp;Jiankang Ou,&nbsp;Zeguo Fang,&nbsp;Qian Zhang,&nbsp;Dong Li","doi":"10.1016/j.tet.2025.134779","DOIUrl":"10.1016/j.tet.2025.134779","url":null,"abstract":"<div><div>An efficient and facile C–H aminocarbonylation of quinone derivatives with isocyanides for the synthesis of corresponding amides was developed. This reaction was promoted by inorganic persulfate under transition-metal free conditions. A broad substrate scope including quinoxalines and quinoxalinones were exhibited by this method, affording the corresponding amides in moderated to good yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134779"},"PeriodicalIF":2.1,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144322057","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
Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[d]pyrimidin]-4-one core 亲电性碘离子介导的4-（5-（芳基乙基）嘧啶-4-基）苯酚的螺旋环化反应生成螺旋[环己[2,5]二烯-1,7'-环五[d]嘧啶]-4- 1核
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-14 DOI: 10.1016/j.tet.2025.134791
Nikolai A. Arutiunov, Stanislav V. Shcherbakov, Daria A. Shtal, Maksim O. Shcheglov, Kirill V. Tolstov, Daria I. Murashkina, Nicolai A. Aksenov, Alexander V. Aksenov
{"title":"Electrophilic iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols enroute to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[d]pyrimidin]-4-one core","authors":"Nikolai A. Arutiunov,&nbsp;Stanislav V. Shcherbakov,&nbsp;Daria A. Shtal,&nbsp;Maksim O. Shcheglov,&nbsp;Kirill V. Tolstov,&nbsp;Daria I. Murashkina,&nbsp;Nicolai A. Aksenov,&nbsp;Alexander V. Aksenov","doi":"10.1016/j.tet.2025.134791","DOIUrl":"10.1016/j.tet.2025.134791","url":null,"abstract":"<div><div>Novel iodonium-ion mediated spirocyclization of 4-(5-(arylethynyl)pyrimidin-4-yl)phenols leading to spiro[cyclohexa[2,5]diene-1,7'-cyclopenta[<em>d</em>]pyrimidin]-4-one core was developed. This sequence, based commercially available reagents starts with acid-catalyzed electrophilic alkylation of phenols with 5-bromopyrimidine. Subsequently, an oxidation, palladium-catalyzed Sonogashira cross-coupling reaction and electrophilic spirocyclization, allowed to target product with good yields and simple synthetic protocols.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134791"},"PeriodicalIF":2.1,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291435","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
Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine 基于咪唑噻唑三嗪邻硝基和间硝基苄基衍生物的新型咪唑噻唑三嗪-吡咯烷-氧吲哚的非对映发散合成
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-14 DOI: 10.1016/j.tet.2025.134782
Alexei N. Izmest'ev , Sergey S. Isakov , Yuri A. Strelenko , Angelina N. Kravchenko , Galina A. Gazieva
{"title":"Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine","authors":"Alexei N. Izmest'ev ,&nbsp;Sergey S. Isakov ,&nbsp;Yuri A. Strelenko ,&nbsp;Angelina N. Kravchenko ,&nbsp;Galina A. Gazieva","doi":"10.1016/j.tet.2025.134782","DOIUrl":"10.1016/j.tet.2025.134782","url":null,"abstract":"<div><div>Four series of dispiro-fused polyheterocyclic compounds containing spiro(pyrrolidine-2,3′-oxindole) and imidazothiazolotriazine moieties were prepared by [3 + 2] cycloaddition of azomethine ylide to <em>ortho</em>- and <em>meta</em>-nitrobenzylidene derivatives of imidazothiazolotriazine. It was shown that ylide cycloaddition occurs to both diastereotopic faces of the dipolarophiles to give the target compounds as two diastereomers. Skeletal rearrangement of the major dispiro(imidazo[4,5-<em>e</em>]thiazolo[3,2-<em>b</em>][1,2,4]triazine-6,3′-pyrrolidin-2′,3″-oxindoles) (<em>anti</em>-<em>exo</em>-diastereomers) gave isomeric dispiro(imidazo[4,5-<em>e</em>]thiazolo[2,3-<em>c</em>][1,2,4]triazine-7,3′-pyrrolidin-2′,3″-oxindoles) (angular <em>syn</em>-<em>exo</em>-diastereomers) that are inaccessible by the direct [3 + 2] cycloaddition reaction.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134782"},"PeriodicalIF":2.1,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144298100","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
Sustainable synthesis of cannabinoids via metal-free aromatic deformylation 通过无金属芳族脱甲酰化可持续合成大麻素
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-13 DOI: 10.1016/j.tet.2025.134789
Gil Dinnar , Oriyan Cohen , Prakash Jagtap , Sanaa Musa
{"title":"Sustainable synthesis of cannabinoids via metal-free aromatic deformylation","authors":"Gil Dinnar ,&nbsp;Oriyan Cohen ,&nbsp;Prakash Jagtap ,&nbsp;Sanaa Musa","doi":"10.1016/j.tet.2025.134789","DOIUrl":"10.1016/j.tet.2025.134789","url":null,"abstract":"<div><div>Cannabinoids, the bioactive compounds of the <em>Cannabis</em> genus, have gained considerable attention for their potential therapeutic applications variety of health conditions. Cannabidiol, in particular, has been studied for its diverse pharmacological properties, including antioxidant, anticancer, anti-inflammatory, and neuroprotective effects. To enhance the accessibility and efficacy of cannabinoids, synthetic approaches have been explored, focusing on improving yields and reducing the creation of unwanted byproducts. This study introduces a novel metal-free deformylation method for synthesizing cannabinoid derivatives from their corresponding cannabinoid aldehyde. We have developed optimized reaction conditions that utilize trimethyl orthoformate as a methanol donor in combination with <em>p</em>-toluenesulfonic acid, which enables high-yield conversion of 3-formyl-cannabinoid to cannabinoid with minimal formation of byproducts. Furthermore, we successfully applied this methodology to a range of other cannabinoid aldehydes, producing cannabinoids with varying alkyl chain lengths. The reaction pathway revealed a nucleophilic substitution mechanism that facilitates the removal of the aldehyde group and promotes efficient cannabinoid synthesis. This metal-free approach offers a sustainable alternative to traditional catalytic methods, which could be really valuable for advancing cannabinoid research and pharmaceutical development.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134789"},"PeriodicalIF":2.1,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291434","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
Base-promoted Annulations of α-Halohydroxamates with 2-(Substituted(tosyl)methyl)phenols for the Synthesis of 1,4-Benzoxazepine Derivatives α-卤代羟基酸酯与2-（取代（甲酰基）甲基）酚的碱基促进环化合成1,4-苯并恶氮平衍生物
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-13 DOI: 10.1016/j.tet.2025.134777
Chenbo Guo , Yi Li , Qiqi Zhang, Wanyu Yan, Jing Zou, Gang Wang, Zhao-Lin He
{"title":"Base-promoted Annulations of α-Halohydroxamates with 2-(Substituted(tosyl)methyl)phenols for the Synthesis of 1,4-Benzoxazepine Derivatives","authors":"Chenbo Guo ,&nbsp;Yi Li ,&nbsp;Qiqi Zhang,&nbsp;Wanyu Yan,&nbsp;Jing Zou,&nbsp;Gang Wang,&nbsp;Zhao-Lin He","doi":"10.1016/j.tet.2025.134777","DOIUrl":"10.1016/j.tet.2025.134777","url":null,"abstract":"<div><div>A base promoted annulation reaction of <em>α</em>-halohydroxamates with 2-(substituted(tosyl)methyl)phenols was developed. The synthetic protocol provided an efficient route to 1,4-benzoxazepine derivatives in moderate to excellent yields under mild condition, exhibiting good functional group tolerance.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134777"},"PeriodicalIF":2.1,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291436","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
Design, synthesis, and photophysical characterization of monoaryl-pyridine-2-ones derivatives: Exploring aggregation-caused quenching vs aggregation-induced emission 单芳基吡啶-2- 1衍生物的设计、合成及光物理表征：探讨聚集引起的猝灭与聚集引起的发射
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-13 DOI: 10.1016/j.tet.2025.134773
Murugesan Preethi, Ajay Dev Ramesh Babu, Sivakumar Shanmugam
{"title":"Design, synthesis, and photophysical characterization of monoaryl-pyridine-2-ones derivatives: Exploring aggregation-caused quenching vs aggregation-induced emission","authors":"Murugesan Preethi,&nbsp;Ajay Dev Ramesh Babu,&nbsp;Sivakumar Shanmugam","doi":"10.1016/j.tet.2025.134773","DOIUrl":"10.1016/j.tet.2025.134773","url":null,"abstract":"<div><div>The dihydropyridine core derivatives have been synthesized from the reaction of 2H-pyrone with hydrazine hydrate, in methanol ethanol solvent, obtained 70–90 %. Under the reflux condition occurred withopening of the lactone ring to yield monoaryl-pyridine-2-ones derivatives <strong>3a-d</strong> in excellent yields. This method's main advantages are short reaction time, high amine utilization, and considerably improved yield. The emission of the molecules 3d can be significantly quenched by picric acid through electron transfer or energy transfer mechanisms, enabling them to function as chemosensors for explosive nitroaryl compound detection.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134773"},"PeriodicalIF":2.1,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144307730","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 methylthiolation of aryl fluorides with S-methylisothiourea sulfate in PEG-400 用s -甲基异硫脲硫酸盐在PEG-400中对芳基氟化物进行无过渡金属甲基硫代化
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-13 DOI: 10.1016/j.tet.2025.134785
Xiangmei Wu, Dayun Huang
{"title":"Transition-metal-free methylthiolation of aryl fluorides with S-methylisothiourea sulfate in PEG-400","authors":"Xiangmei Wu,&nbsp;Dayun Huang","doi":"10.1016/j.tet.2025.134785","DOIUrl":"10.1016/j.tet.2025.134785","url":null,"abstract":"<div><div>A simple method for methylthiolation has been developed to produce various aryl methyl sulfides in moderate to good yields. This method uses inexpensive aryl fluorides as starting materials and S-methylisothiourea sulfate as the thiomethyl source. Halogen atoms like iodine, bromine, and chlorine are well tolerated. This simplifies further product transformations. Besides, this approach is catalyst-free. The reaction conditions are simple, the starting materials are readily available, and the solvent used is PEG-400, making the system more environmentally friendly.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134785"},"PeriodicalIF":2.1,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144322059","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
Evaluation of C3-substituents on pyrazoles as remote directing groups in palladium-catalyzed direct arylation 钯催化直接芳化反应中吡唑上的c3取代基作为远端导向基团的评价
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-13 DOI: 10.1016/j.tet.2025.134783
Besma Saoudi , Norman Le Floch , Henri Doucet
{"title":"Evaluation of C3-substituents on pyrazoles as remote directing groups in palladium-catalyzed direct arylation","authors":"Besma Saoudi ,&nbsp;Norman Le Floch ,&nbsp;Henri Doucet","doi":"10.1016/j.tet.2025.134783","DOIUrl":"10.1016/j.tet.2025.134783","url":null,"abstract":"<div><div>The palladium-catalyzed C–H bond functionalization of pyrazoles frequently presents significant challenges in terms of control of the selectivity of the reaction. This is due to the similar reactivity of their C4 and C5 positions, which frequently leads to the formation of mixtures of C4- and C5-mono-arylated pyrazoles, as well as C4,C5-di-arylated pyrazoles. This study demonstrates that the incorporation of suitable substituents at the C3-position of pyrazoles, such as trifluoromethyl or formyl, can result in the regioselective formation of the C5-arylated pyrazoles. These reactions demonstrate a high degree of tolerance for a variety of substituents on the aryl bromide. Moreover, our procedure utilizes an air-stable palladium catalyst that is readily available and a cost-effective base. In contrast, the presence of nitrile or bromo substituents at the C3-position of pyrazoles resulted in the formation of mixtures of products.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134783"},"PeriodicalIF":2.1,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144322058","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
Photocatalytic CO2 reduction to formate using triarylphosphine as reductant 以三芳基膦为还原剂光催化CO2还原成甲酸盐
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-13 DOI: 10.1016/j.tet.2025.134787
Jiasheng Xu, Suguru Murakami, Tatsuhiro Harada, Weibin Xie, Tatsushi Yabuta, Masahiko Hayashi, Ryosuke Matsubara
{"title":"Photocatalytic CO2 reduction to formate using triarylphosphine as reductant","authors":"Jiasheng Xu,&nbsp;Suguru Murakami,&nbsp;Tatsuhiro Harada,&nbsp;Weibin Xie,&nbsp;Tatsushi Yabuta,&nbsp;Masahiko Hayashi,&nbsp;Ryosuke Matsubara","doi":"10.1016/j.tet.2025.134787","DOIUrl":"10.1016/j.tet.2025.134787","url":null,"abstract":"<div><div>The increasing concentration of CO<sub>2</sub> in the Earth's atmosphere represents a pressing global challenge for humanity. The reduction of CO<sub>2</sub> to formate offers a promising strategy for carbon capture and utilization, thereby contributing to the realization of sustainable development. In this study, the photocatalytic reduction of CO<sub>2</sub> using triarylphosphine as a reductant was investigated. However, due to the higher oxidation potential of triarylphosphine compared to the employed photosensitizer (PS), efficient regeneration of the PS poses a significant challenge. This issue was successfully addressed by introducing aryl thiol as a crucial co-catalyst in the reaction. Mechanistic studies revealed that the formation and cleavage of phosphorus–sulfur bonds drive the otherwise unfavored electron transfer process. These findings provide valuable insights toward the development of catalytic systems capable of utilizing reductants with even higher oxidation potentials.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134787"},"PeriodicalIF":2.1,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144298003","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
[CMMIM][BF4] ionic liquid catalyzed efficient synthesis of henna based xanthene derivatives and their photophysical, theoretical and molecular docking studies [CMMIM][BF4]离子液体催化高效合成指甲花基杂蒽衍生物及其光物理、理论和分子对接研究
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-10 DOI: 10.1016/j.tet.2025.134774
Venkatesan Kali , Sai Deepak Pasuparthy , Barnali Maiti
{"title":"[CMMIM][BF4] ionic liquid catalyzed efficient synthesis of henna based xanthene derivatives and their photophysical, theoretical and molecular docking studies","authors":"Venkatesan Kali ,&nbsp;Sai Deepak Pasuparthy ,&nbsp;Barnali Maiti","doi":"10.1016/j.tet.2025.134774","DOIUrl":"10.1016/j.tet.2025.134774","url":null,"abstract":"<div><div>Henna-based xanthene and its derivatives represent a significant class of heterocyclic compounds, exhibiting a wide range of pharmacological and biological activities. In this article, we present a revamped method for the synthesis of henna-based xanthene derivatives by using 4 mol% of [CMMIM][BF<sub>4</sub>] ionic liquid in a one pot, metal-free, eco-friendly aqueous ethanol solvent at 80 °C. A series of 32 derivatives were synthesized in 20–50 min, with yields of up to 92 %, and were characterized using various spectroscopic methods. UV–Visible and fluorescence spectroscopy were utilized to investigate the photophysical properties of synthesized henna-based xanthene derivatives. The absorption and emission spectra exhibited peak wavelengths (<em>λ</em><sub>max</sub>) ranging from 395 to 410 nm and 413 to 415 nm, respectively. Theoretical studies revealed a trend consistent with experimental results. Furthermore, molecular docking using AutoDock Vina was performed to evaluate the binding interactions of the synthesized derivatives with Bovine Serum Albumin (BSA) and deoxyribonucleic acid (DNA), demonstrating binding affinities between −8.0 to −11.5 kcal/mol<sup>−1</sup> for BSA and −8.5 to −10.9 kcal/mol<sup>−1</sup> for DNA.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134774"},"PeriodicalIF":2.1,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291433","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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