Synthetic Communications最新文献

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A novel strategy for the efficient synthesis of Erianin 一种高效合成羊角苷的新方法
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-16 DOI: 10.1080/00397911.2025.2505903
Wenpei Zhang (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Xinyue Pan (Investigation) , Jie He (Supervision) , Yirong Lin (Visualization) , Fengyang Zhang (Validation) , Li Guo (Validation) , Jieqing Liu (Conceptualization Funding acquisition Project administration Resources)
{"title":"A novel strategy for the efficient synthesis of Erianin","authors":"Wenpei Zhang (Data curation Investigation Methodology Writing – original draft Writing – review & editing) ,&nbsp;Xinyue Pan (Investigation) ,&nbsp;Jie He (Supervision) ,&nbsp;Yirong Lin (Visualization) ,&nbsp;Fengyang Zhang (Validation) ,&nbsp;Li Guo (Validation) ,&nbsp;Jieqing Liu (Conceptualization Funding acquisition Project administration Resources)","doi":"10.1080/00397911.2025.2505903","DOIUrl":"10.1080/00397911.2025.2505903","url":null,"abstract":"<div><div>Erianin, a natural biphenyl compound found in Dendrobium, exhibits significant pharmacological effects, including anti-tumor and anti-inflammatory properties. Here, we report a novel and efficient three-step synthetic route for Erianin, utilizing homovanillic acid and 3,4,5-trimethoxybenzaldehyde as starting materials. Our method integrates hydroxyaldehyde condensation, microwave-assisted decarboxylation, and mild double bond reduction, achieving a total yield of 45.3%—a 47.7% improvement over prior approaches. The developed protocol provides a cost-effective and scalable approach to access Erianin, offering significant potential for therapeutic research and drug development.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 852-861"},"PeriodicalIF":1.8,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124337","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
2-Aminopyridine schiff base compounds: Synthesis, characterization, anti-bacterial properties, molecular docking and computational studies 2-氨基吡啶席夫碱化合物:合成、表征、抗菌特性、分子对接和计算研究
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-14 DOI: 10.1080/00397911.2025.2501761
Keerthana L. (Formal analysis Methodology Writing – original draft) , Sharulatha V. (Supervision Writing – review & editing) , Rajan V. K. (Formal analysis Software)
{"title":"2-Aminopyridine schiff base compounds: Synthesis, characterization, anti-bacterial properties, molecular docking and computational studies","authors":"Keerthana L. (Formal analysis Methodology Writing – original draft) ,&nbsp;Sharulatha V. (Supervision Writing – review & editing) ,&nbsp;Rajan V. K. (Formal analysis Software)","doi":"10.1080/00397911.2025.2501761","DOIUrl":"10.1080/00397911.2025.2501761","url":null,"abstract":"<div><div>The synthesis and characterization of Schiff bases based on 3, 4, 5-trimethoxy benzaldehyde and 2-aminopyridine derivatives 3a to 3i were done using FT-IR, <sup>1</sup>H NMR and <sup>13</sup>CNMR and Mass spectral studies. The antibacterial properties of the compounds were assessed with two gram-positive bacteria, <em>Bacillus subtilis</em> and <em>Staphylococcus aureus</em>, and two gram-negative bacteria, <em>Pseudomonas aeruginosa</em> and <em>Escherichia coli.</em> Compounds <strong>3h</strong> and <strong>3j</strong> exhibited greater activity than standard against <em>S. aureus</em> and <em>E. coli.</em> Molecular docking, cited several type interactions among the target proteins and Schiff base compounds including H-bond, Alkyl, Van der Waals and π–alkyl interactions. DFT calculations confirmed that the <em>cis</em> form of all the synthesized compounds were stable more than the <em>trans</em> form. Global reactive descriptors calculation indicated that the maximum reactivity of compound <strong>3f</strong> present in IV quadrant while all the other compounds were present in I and III quadrant indicated the good reactivity rate compared to reference.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 825-851"},"PeriodicalIF":1.8,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124338","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
Green synthesis and anticancer evaluation of novel bis-(trifluoromethyl-5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridine scaffolds 新型双-(三氟甲基-5-苯基-1,3,4-恶二唑-2-基)甲基)-1,8-萘啶支架的绿色合成及抗癌评价
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-12 DOI: 10.1080/00397911.2025.2501211
Mahesh Ellanti (Conceptualization Data curation Validation Writing – review & editing) , Divya A (Software) , Kavati Shireesha (Visualization) , Kumara Swamy Jella (Supervision)
{"title":"Green synthesis and anticancer evaluation of novel bis-(trifluoromethyl-5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridine scaffolds","authors":"Mahesh Ellanti (Conceptualization Data curation Validation Writing – review & editing) ,&nbsp;Divya A (Software) ,&nbsp;Kavati Shireesha (Visualization) ,&nbsp;Kumara Swamy Jella (Supervision)","doi":"10.1080/00397911.2025.2501211","DOIUrl":"10.1080/00397911.2025.2501211","url":null,"abstract":"<div><div>Eco-friendly construction of a 3-(3,5-bis(trifluoromethyl)phenyl)-1-((5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridin-2(1H)-one derivatives (<strong>10a–j</strong>) under microwave method furnished excellent yields in minimal time with maximum selectivity in the presence of PhI(OAc)<sub>2</sub>. This route aligns with the principles of green chemistry due to its significantly reduced reaction time and enriched energy efficiency, simplicity, and high yields. The synthesized compounds were characterized by spectroscopic ­techniques IR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, Mass spectrometry, and elemental analysis studies. All the synthesized compounds cytotoxicity was tested against four cancer cell lines, MCF-7, Colo-205, A549, and SiHa human Cervix cancer cell lines; all the compounds demonstrated remarkable <em>in vitro</em> anticancer activity, notably, among them, compound 10i exhibited the most potent anti-cancer activity of IC<sub>50</sub> valves are 11.21 ± 0.17 μM (MCF-7 breast cancer cell line), 11.62 ± 0.54 μM (Colo-205 colon cancer cell line), 17.85 ± 0.48 μM (A549 lung carcinoma epithelial cells), 19.64 ± 0.46 μM (SiHa human Cervix cancer cell line) compared with clinical standard drug.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 815-824"},"PeriodicalIF":1.8,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124340","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
Squaric acid as an organocatalyst for Knoevenagel condensation and 1,6-conjugate addition reactions 方酸作为Knoevenagel缩合和1,6-共轭加成反应的有机催化剂
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-07 DOI: 10.1080/00397911.2025.2500720
Nirmal Singh (Conceptualization Formal analysis Methodology Writing – original draft) , Ankur G Pandey (Writing – review & editing)
{"title":"Squaric acid as an organocatalyst for Knoevenagel condensation and 1,6-conjugate addition reactions","authors":"Nirmal Singh (Conceptualization Formal analysis Methodology Writing – original draft) ,&nbsp;Ankur G Pandey (Writing – review & editing)","doi":"10.1080/00397911.2025.2500720","DOIUrl":"10.1080/00397911.2025.2500720","url":null,"abstract":"<div><div>Catalysts play an integral role in rationalizing several organic reactions despite suffering major challenges like poor efficiency, high cost and toxicity. In this work, we have reported a green, cost effective and highly efficient squaric acid as an organocatalyst for catalyzing two of the most vital organic reactions, Knoevenagel condensation and 1,6-conjugate addition reactions. Under our optimized conditions, the organocatayst showed excellent yields of up to 94% for both the reactions with an extensive substrate scope and excellent reusability for multiple reaction cycles. In addition, the catalytic efficacy of squaric acid was showcased by employing it in the synthesis of 2-amino-<em>4H</em>-chromene derivatives.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 804-814"},"PeriodicalIF":1.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124369","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
DTBP mediated tandem oxidative reaction of o-aminobenzamides with alcohols for the synthesis of quinazolinones 邻氨基苯醚介导邻氨基苯酰胺与醇的串联氧化反应合成喹唑啉酮
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-05 DOI: 10.1080/00397911.2025.2500050
Jin Li (Investigation Writing – original draft) , Haotian Cao (Investigation Methodology) , Hongyou Tian (Data curation Investigation) , Huaju Li (Data curation) , Yongke Hu (Funding acquisition Project administration Writing – review & editing)
{"title":"DTBP mediated tandem oxidative reaction of o-aminobenzamides with alcohols for the synthesis of quinazolinones","authors":"Jin Li (Investigation Writing – original draft) ,&nbsp;Haotian Cao (Investigation Methodology) ,&nbsp;Hongyou Tian (Data curation Investigation) ,&nbsp;Huaju Li (Data curation) ,&nbsp;Yongke Hu (Funding acquisition Project administration Writing – review & editing)","doi":"10.1080/00397911.2025.2500050","DOIUrl":"10.1080/00397911.2025.2500050","url":null,"abstract":"<div><div>A practical and efficient methodology for the construction of quinazolinones from readily available alcohols and <em>o</em>-aminobenzamides in the presence of DTBP/Cu(OTf)<sub>2</sub> has been developed. This catalytic system exhibits good functional group tolerance and could afford a range of quinazolinones in good to excellent yields. In case of gram-scale reaction, 2-phenylquinazolin-4(3<em>H</em>)-one (<strong>3a</strong>) was obtained in 86% isolated yield, which indicated this protocol was amenable to scale up and had a potential value in industry. In addition, a plausible reaction mechanism involving a radical process has been proposed, and further applications of this catalytic system are under way in our laboratory.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 774-782"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948411","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 antimycobacterial evaluation of benzimidazole-thiazolylhydrazone derivatives: In silico molecular docking studies, DFT analysis and ADMET predictions 苯并咪唑-噻唑腙衍生物的设计、合成和抑菌评价:硅分子对接研究、DFT分析和ADMET预测
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-05 DOI: 10.1080/00397911.2025.2498535
Arya C. G. (Data curation Formal analysis Methodology Writing – original draft) , Jyothi Kumari (Data curation Formal analysis) , Siddhardha Busi (Data curation Formal analysis Investigation Writing – review & editing) , Simi Asma Salim (Data curation Formal analysis) , Munugala Chandrakanth (Data curation Formal analysis Software) , Dharmarajan Sriram (Data curation Formal analysis Investigation Writing – review & editing) , Ramesh Gondru (Data curation Formal analysis Software Visualization Writing – review & editing) , Janardhan Banothu (Conceptualization Funding acquisition Investigation Project administration Resources Supervision Validation Visualization Writing – review & editing)
{"title":"Design, synthesis and antimycobacterial evaluation of benzimidazole-thiazolylhydrazone derivatives: In silico molecular docking studies, DFT analysis and ADMET predictions","authors":"Arya C. G. (Data curation Formal analysis Methodology Writing – original draft) ,&nbsp;Jyothi Kumari (Data curation Formal analysis) ,&nbsp;Siddhardha Busi (Data curation Formal analysis Investigation Writing – review & editing) ,&nbsp;Simi Asma Salim (Data curation Formal analysis) ,&nbsp;Munugala Chandrakanth (Data curation Formal analysis Software) ,&nbsp;Dharmarajan Sriram (Data curation Formal analysis Investigation Writing – review & editing) ,&nbsp;Ramesh Gondru (Data curation Formal analysis Software Visualization Writing – review & editing) ,&nbsp;Janardhan Banothu (Conceptualization Funding acquisition Investigation Project administration Resources Supervision Validation Visualization Writing – review & editing)","doi":"10.1080/00397911.2025.2498535","DOIUrl":"10.1080/00397911.2025.2498535","url":null,"abstract":"<div><div>Tuberculosis (TB) remains a significant global health challenge, with 10 million new cases and 1 million deaths annually. The limited availability of anti-TB drugs, prolonged treatment regimens, and drug resistance underscores the urgent need for new therapeutic agents. Leveraging the pharmacological potential of benzimidazole and thiazolylhydrazone scaffolds, we designed and synthesized a series of novel benzimidazole-thiazolylhydrazone derivatives. These compounds were prepared <em>via</em> reactions of phenacyl bromides with thiosemicarbazide and benzimidazole-containing arylaldehydes in ethanol with catalytic acetic acid. <em>In vitro</em> testing against <em>Mycobacterium tuberculosis</em> (H37Rv) revealed notable activity for 4-fluorophenyl (<strong>4b</strong>) and 4-bromophenyl (<strong>4d</strong>) derivatives, with MIC values of 3.125 μg/mL and 6.25 μg/mL, respectively. Molecular docking suggested compound <strong>4b</strong> targets DprE1, crucial in mycobacterial cell wall synthesis, with a binding energy of −10.9 kcal/mol. <em>In silico</em> ADME analysis confirmed drug-likeness, and TOPKAT studies indicated non-carcinogenicity. These results position compound <strong>4b</strong> as a promising lead for further TB drug development.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 758-773"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948410","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
Iron catalyzed N-arylation of 7-azaindole with aryl iodides 铁催化7-叠氮吲哚与芳基碘化物的n -芳化反应
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-05 DOI: 10.1080/00397911.2025.2496968
Yong-Chua Teo (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) , Ying-Rui Tan (Investigation Methodology) , Wei-Zhi Ang (Investigation Methodology) , Anthia Shun-Ai Teo (Investigation Methodology)
{"title":"Iron catalyzed N-arylation of 7-azaindole with aryl iodides","authors":"Yong-Chua Teo (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) ,&nbsp;Ying-Rui Tan (Investigation Methodology) ,&nbsp;Wei-Zhi Ang (Investigation Methodology) ,&nbsp;Anthia Shun-Ai Teo (Investigation Methodology)","doi":"10.1080/00397911.2025.2496968","DOIUrl":"10.1080/00397911.2025.2496968","url":null,"abstract":"<div><div>A simple and efficient ligand-assisted iron-catalyzed system for the C-N coupling of 7-azaindole with aryl iodides was developed using water as the sole solvent. Under the optimum conditions, the N-arylated products were obtained in good yields up to 96%.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 739-748"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948427","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
A sequential multicomponent reaction toward the construction of a novel contiguous imino-thiazolidinone grafted dispiroheterocyclic scaffolds 构建一种新型连续亚胺噻唑烷酮接枝双杂环支架的顺序多组分反应
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-03 DOI: 10.1080/00397911.2025.2454961
Sunita Yadav ,  Ankita , Aakash Singh , Ruby Singh
{"title":"A sequential multicomponent reaction toward the construction of a novel contiguous imino-thiazolidinone grafted dispiroheterocyclic scaffolds","authors":"Sunita Yadav ,&nbsp; Ankita ,&nbsp;Aakash Singh ,&nbsp;Ruby Singh","doi":"10.1080/00397911.2025.2454961","DOIUrl":"10.1080/00397911.2025.2454961","url":null,"abstract":"<div><div>Synthesis of structurally intriguing iminothiazolidinone tethered dispiropyrrolizidine/pyrrolothiazole hybrids have been achieved with complete regio- and diastereoselectivity in excellent yields <em>via</em> a one-pot three component 1,3-dipolar cycloaddition strategy employing alkyl-2-[(<em>Z</em>)-4-oxo-3-aryl/alkyl-2-(arylimino)thiazolidin-5-ylidene] acetates as dipolarophiles and azomethine ylide derived from two cyclic ketones (isatin and acenaphthaquinone) and cyclic amino acids (<span>l</span>-proline and <span>l</span>-thiaproline) using biodegradable deep eutectic solvent. During the entire transformation, three additional bonds are formed with generation of four stereogenic carbons in target molecule in a single step reaction. The synthesized compounds were structurally elucidated using NMR spectroscopic studies, and the regio-and stereoselectivity was determined through single crystal X-ray diffraction study.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 631-642"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929192","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 benzimidazole-derived chiral cyclic phosphoric acid and its application in asymmetric induction process 苯并咪唑类手性环磷酸的合成及其在不对称诱导中的应用
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-03 DOI: 10.1080/00397911.2025.2495140
Swapnil J. Wagh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Baludev D. Dadas (Formal analysis Investigation Writing – original draft Writing – review & editing) , Trupti S. Tawde (Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Sumaiya Shaikh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Anil V. Karnik (Conceptualization Investigation Methodology Project administration Supervision Visualization Writing – original draft Writing – review & editing)
{"title":"Synthesis of benzimidazole-derived chiral cyclic phosphoric acid and its application in asymmetric induction process","authors":"Swapnil J. Wagh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) ,&nbsp;Baludev D. Dadas (Formal analysis Investigation Writing – original draft Writing – review & editing) ,&nbsp;Trupti S. Tawde (Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) ,&nbsp;Sumaiya Shaikh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) ,&nbsp;Anil V. Karnik (Conceptualization Investigation Methodology Project administration Supervision Visualization Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2495140","DOIUrl":"10.1080/00397911.2025.2495140","url":null,"abstract":"<div><div>Chiral-pool approach has been invoked in a three-step synthetic protocol for the synthesis of 9-membered Benzimidazole-derived organo-Phosphoric Acid (HEBEN-PA). The HEBEN-PA has two fused aryl rings incorporated in the structure to minimize conformational changes. The HEBEN-PA was successfully employed as a Chiral Bronsted acid catalyst for the enantiomerically enriched dihydroquinazolinone synthesis. Synthesis of dihydroquinazolinone occurred with good yields. Effect of solvent, temperature, and the substituents on the level of enantioselectivity have been examined.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 643-651"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929193","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 amides via TBN-induced oxidation cross-coupling of acetonitrile and N-sulfinylanilines 乙腈与n -亚砜苯胺的tbn诱导氧化交偶联合成酰胺
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2025-05-03 DOI: 10.1080/00397911.2025.2494245
Quansen Wu (Methodology Writing – review & editing) , Zizhong Ma (Data curation) , Rui Li (Methodology) , Ruiqiang Shang (Methodology) , Zhenyu An (Writing – original draft) , Yafeng Liu (Writing – original draft) , Qing Huang (Writing – review & editing) , Zhenjie Qi (Conceptualization Funding acquisition Project administration Writing – original draft Writing – review & editing)
{"title":"Synthesis of amides via TBN-induced oxidation cross-coupling of acetonitrile and N-sulfinylanilines","authors":"Quansen Wu (Methodology Writing – review & editing) ,&nbsp;Zizhong Ma (Data curation) ,&nbsp;Rui Li (Methodology) ,&nbsp;Ruiqiang Shang (Methodology) ,&nbsp;Zhenyu An (Writing – original draft) ,&nbsp;Yafeng Liu (Writing – original draft) ,&nbsp;Qing Huang (Writing – review & editing) ,&nbsp;Zhenjie Qi (Conceptualization Funding acquisition Project administration Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2494245","DOIUrl":"10.1080/00397911.2025.2494245","url":null,"abstract":"<div><div>A novel method for the synthesis of amides has been developed that features – <em>tert</em>-butyl nitrite-induced oxidative cross-coupling of acetonitrile with <em>N</em>-sulfinylanilines. Acetonitrile serves as the C2 building block in this process. The present protocol effectively inhibits the competition with the C≡N triple bond but enables the in <em>situ</em> formation of unsaturated C–O bond. The reaction demonstrates a broad substrate scope and can be conducted under mild conditions. Mechanistic studies, including radical trapping experiments and H<sub>2</sub><sup>18</sup>O-labeling, confirm a radical-mediated pathway involving acetonitrile-derived intermediates. Additionally, this method is amenable to gram-scale synthesis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 652-660"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929191","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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