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Synthesis of spiroisoxazoline oxindoles by base-promoted annulation of oxime esters and isatins 碱促进肟酯和isatins环化法合成螺代异恶唑啉氧吲哚
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-06 DOI: 10.1016/j.tetlet.2025.155506
Si-Wei Chen , Xu-Hua Hu , Ling Wu , Chun-Bao Miao , Xun-Xiang Guo
{"title":"Synthesis of spiroisoxazoline oxindoles by base-promoted annulation of oxime esters and isatins","authors":"Si-Wei Chen ,&nbsp;Xu-Hua Hu ,&nbsp;Ling Wu ,&nbsp;Chun-Bao Miao ,&nbsp;Xun-Xiang Guo","doi":"10.1016/j.tetlet.2025.155506","DOIUrl":"10.1016/j.tetlet.2025.155506","url":null,"abstract":"<div><div>A base-promoted annulation reaction of oxime esters and isatins has been developed for the facile and rapid synthesis of spiroisoxazoline oxindoles. This method demonstrates high efficiency, enabling the synthesis of a variety of spiroisoxazoline oxindoles with good to high yields under simple and mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155506"},"PeriodicalIF":1.5,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143550160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Ortho-nitrochalcones by solvent-free grinding method: Facilitating the synthesis of 2,3-Disubstituted Quinoline N-oxides via bimolecular reaction 无溶剂研磨法合成邻硝基查尔酮：促进了2,3-二取代喹啉n -氧化物的双分子合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-05 DOI: 10.1016/j.tetlet.2025.155533
Sai Wang , Wangyuan Zhan , Deguang Huang , XiaoFeng Zhang
{"title":"Synthesis of Ortho-nitrochalcones by solvent-free grinding method: Facilitating the synthesis of 2,3-Disubstituted Quinoline N-oxides via bimolecular reaction","authors":"Sai Wang ,&nbsp;Wangyuan Zhan ,&nbsp;Deguang Huang ,&nbsp;XiaoFeng Zhang","doi":"10.1016/j.tetlet.2025.155533","DOIUrl":"10.1016/j.tetlet.2025.155533","url":null,"abstract":"<div><div>A method for the synthesis of 2,3-disubstituted quinoline N-oxides, <em>ortho</em>-nitrochalcones, and their derivatives is reported. Through mortar-pestle grinding under solvent-free conditions, a series of <em>ortho</em>-nitrochalcone derivatives, naphthalenone derivatives, and indenone derivatives were obtained in good to excellent yields. Additionally, by using <em>ortho</em>-nitrochalcones and their derivatives along with 2-nitrobenzaldehyde as starting materials, in the presence of a specific ratio of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and sodium hydroxide (NaOH), and with 1,2-diphenylhydrazine involved, 2,3-disubstituted quinoline N-oxides were synthesized through a bimolecular reaction. This synthetic approach features metal-free catalysis, employs inexpensive and easily accessible raw materials, and operates under mild reaction conditions, thereby enriching the research domain of organic synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155533"},"PeriodicalIF":1.5,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143620806","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Greener synthesis of Pyrroloacridine-1(2H)-one and 1,8-Dioxodecahydroacridine derivatives: Ascorbic acid mediated OrganocatalyticApproach 吡咯吖啶-1(2H)- 1和1,8-二氧十二氢吖啶衍生物的绿色合成：抗坏血酸介导的有机催化方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155518
Saptadwipa Bhattacharjee, Puja Basak, Pranab Ghosh
{"title":"Greener synthesis of Pyrroloacridine-1(2H)-one and 1,8-Dioxodecahydroacridine derivatives: Ascorbic acid mediated OrganocatalyticApproach","authors":"Saptadwipa Bhattacharjee,&nbsp;Puja Basak,&nbsp;Pranab Ghosh","doi":"10.1016/j.tetlet.2025.155518","DOIUrl":"10.1016/j.tetlet.2025.155518","url":null,"abstract":"<div><div>A simple, one-pot multi component synthetic route employing ascorbic acid is reported for synthesising pyrrolo[2,3,4-<em>kl</em>]acridin and 1,8-dioxodecahydroacridine derivatives under solvent free condition. This method offers advantages such as moderate conditions, ease of operation, environmental friendliness, and organocatalyst. The suggested technique features green reaction conditions, a broad substrate scope, operational simplicity, an eco-efficient catalyst, the production of C<img>N bonds, and excellent product yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155518"},"PeriodicalIF":1.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143580732","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Nitration of deactivated aromatic compounds using Lithium nitrate 硝酸锂对失活芳香族化合物的硝化作用
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155515
Weihao Ma , J. Tyler McBride , Robert S. Phillips
{"title":"Nitration of deactivated aromatic compounds using Lithium nitrate","authors":"Weihao Ma ,&nbsp;J. Tyler McBride ,&nbsp;Robert S. Phillips","doi":"10.1016/j.tetlet.2025.155515","DOIUrl":"10.1016/j.tetlet.2025.155515","url":null,"abstract":"<div><div>Nitroarenes are critically important in medicinal chemistry, material science, and the chemical industry. In this paper, we introduce a new strategy for the electrophilic nitration of deactivated aromatic compounds, utilizing lithium nitrate (LiNO<sub>3</sub>) in the presence of sulfuric acid in trifluoroacetic acid. This method has demonstrated moderate to excellent yield. Mild reaction conditions and easy workup make the synthesis of nitro compounds both practical and commercially feasible.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155515"},"PeriodicalIF":1.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143562270","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 bis-sulfonium lipids and their antibacterial ability 双磺酸脂的合成及其抗菌性能
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155528
Chengcai Liu , Xiaodong Zhou , Xinrui Bi , Peiyu Chen , Wanning Li , Jing Li
{"title":"Synthesis of bis-sulfonium lipids and their antibacterial ability","authors":"Chengcai Liu ,&nbsp;Xiaodong Zhou ,&nbsp;Xinrui Bi ,&nbsp;Peiyu Chen ,&nbsp;Wanning Li ,&nbsp;Jing Li","doi":"10.1016/j.tetlet.2025.155528","DOIUrl":"10.1016/j.tetlet.2025.155528","url":null,"abstract":"<div><div>Gemini cationic surfactants have great advantages as antibacterial agents. Herein, a group of bis-sulfonium lipids was synthesized and their antibacterial activities were investigated on Gram-negative and Gram-positive bacterial stains. The activity of bis-sulfonium lipids was related to the hydrophobic substitution. When each of the sulfonium contained one long alkyl chain and the spacer was short, the gemini salt exhibited strong inhibition. The compound with benzyl, decyl and pentylene spacer exhibited the broad antibacterial activity, and was more sensitive on Gram-negative than commercial quaternary ammonium salts. The mechanism study showed that increasing cell membrane permeability and disrupting the cell membrane are important pathways for inhibiting bacteria.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155528"},"PeriodicalIF":1.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143580733","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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-pot synthesis and anti-proliferative activity of hindered 5-amino-1-alkylimidazole-4-carboxamides 受阻5-氨基-1-烷基咪唑-4-羧酰胺的一锅合成及其抗增殖活性
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155517
Yamei Zhang , Zijuan Yang , Yong Xie , Yeming Wang
{"title":"One-pot synthesis and anti-proliferative activity of hindered 5-amino-1-alkylimidazole-4-carboxamides","authors":"Yamei Zhang ,&nbsp;Zijuan Yang ,&nbsp;Yong Xie ,&nbsp;Yeming Wang","doi":"10.1016/j.tetlet.2025.155517","DOIUrl":"10.1016/j.tetlet.2025.155517","url":null,"abstract":"<div><div>One-pot procedure was developed for the synthesis of hindered 5-amino-1-alkylimidazole-4-carboxamides by using bulky alkyl amines with trimethyl orthoformate and 2-amino-2-cyanoacetamide. Under optimized conditions, the reactivity of a series of steric hindrance substrates was examined, producing the corresponding hindered 5-amino-1-alkylimidazole-4-carboxamides with good to excellent yields. This synthetic method has several advantages including metal- and additive-free, short reaction time and wide substrate scope with good to excellent yields. Besides, 5-amino-1-(4-fluorobenzyl)-1<em>H</em>-imidazole-4-carboxamide (<strong>3j</strong>) exhibited potent antiproliferative activity against A375(B-RAF<sup>V600E</sup>) cells as a novel anti-tumor agent, and the molecular docking model showed that carboxamide moiety of <strong>3j</strong> was a key active functional group, forming two hydrogen bonds with Lys483 and Phe595，which was similar to the function of sulfonamide of vemurafenib. To our delight, the imidazole scaffold of <strong>3j</strong> formed a novel hydrogen bond with Asp594, and there was π…π interaction between the phenyl group of <strong>3j</strong> and Phe583, which were different from binding mode of vemurafenib. The binding mode between <strong>3j</strong> and B-RAF<sup>V600E</sup> kinase provided a reasonable explanation for <strong>3j</strong> as a potential B-RAF<sup>V600E</sup> kinase inhibitor.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155517"},"PeriodicalIF":1.5,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143580730","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Salviamone, a norabietane diterpenoid from Salvia roborowskii Maxim and structural revisions of tanshinketolactone and prioketolactone 从鼠尾草中提取的去甲比烷二萜类鼠尾草酮及丹参酮内酯和丙酮内酯的结构修正
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-27 DOI: 10.1016/j.tetlet.2025.155519
Mi-Na Yang, Xin Wang, Li-Jia Ye, Le-Le Guo, Yu-Bin Lu, Yi-Nan Yang, Miao Zhang, Zhan-Xin Zhang, Dong-Qing Fei
{"title":"Salviamone, a norabietane diterpenoid from Salvia roborowskii Maxim and structural revisions of tanshinketolactone and prioketolactone","authors":"Mi-Na Yang,&nbsp;Xin Wang,&nbsp;Li-Jia Ye,&nbsp;Le-Le Guo,&nbsp;Yu-Bin Lu,&nbsp;Yi-Nan Yang,&nbsp;Miao Zhang,&nbsp;Zhan-Xin Zhang,&nbsp;Dong-Qing Fei","doi":"10.1016/j.tetlet.2025.155519","DOIUrl":"10.1016/j.tetlet.2025.155519","url":null,"abstract":"<div><div>One norabietane diterpenoid named salviamone (<strong>1</strong>) was isolated from the whole plants of <em>Salvia roborowskii</em> Maxim. Comparison of spectrometric data of <strong>1</strong> with the data of the previously reported tanshinketolactone and prioketolactone, strongly suggested that these metabolites were identical. Due to the existence of many quaternary carbons, we cannot fully determine the planar structure of these compounds through the 2D NMR spectrometric data. Thus, we suggested the structures of tanshinketolactone and prioketolactone were revised to salviamone by an analysis of statistical DP4+ analyses based on DFT-GIAO NMR calculations. Furthermore, the absolute configuration of <strong>1</strong> was determined for the first time by quantum chemistry ECD calculations.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155519"},"PeriodicalIF":1.5,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507960","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Alkylcyanation of unactivated alkenes via photoinduced hydrogen atom transfer and 1,4-cyano migration 通过光诱导氢原子转移和1,4-氰基迁移的非活化烯烃的烷基氰化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-27 DOI: 10.1016/j.tetlet.2025.155516
Meichen Xu , Pandaram Sakthivel , Zongyang Ma , Juntao Ye
{"title":"Alkylcyanation of unactivated alkenes via photoinduced hydrogen atom transfer and 1,4-cyano migration","authors":"Meichen Xu ,&nbsp;Pandaram Sakthivel ,&nbsp;Zongyang Ma ,&nbsp;Juntao Ye","doi":"10.1016/j.tetlet.2025.155516","DOIUrl":"10.1016/j.tetlet.2025.155516","url":null,"abstract":"<div><div>1,2-Dicarbofunctionalization of alkenes represents a step-economical strategy for introducing two functional groups simultaneously in organic synthesis. Herein, we report a visible-light-driven alkylcyanation of unactivated alkenes via hydrogen atom transfer (HAT) and cyano migration. Mechanistic studies suggest that a quinuclidineboryl radical serves as an effective hydridic HAT catalyst, facilitating the generation of electrophilic alkyl radicals. This method features mild reaction conditions and good compatibility with a diverse array of functional groups.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155516"},"PeriodicalIF":1.5,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143550725","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 Mannich reactions of α-ketoesters catalyzed through noncovalent interactions: Differences between pyruvates and substituted pyruvates in the formation of nucleophilic species 通过非共价相互作用催化α-酮酯的不对称曼尼希反应：丙酮酸酯和取代丙酮酸酯在亲核物质形成中的差异
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-22 DOI: 10.1016/j.tetlet.2025.155514
Santanu Mondal, Fujie Tanaka
{"title":"Asymmetric Mannich reactions of α-ketoesters catalyzed through noncovalent interactions: Differences between pyruvates and substituted pyruvates in the formation of nucleophilic species","authors":"Santanu Mondal,&nbsp;Fujie Tanaka","doi":"10.1016/j.tetlet.2025.155514","DOIUrl":"10.1016/j.tetlet.2025.155514","url":null,"abstract":"<div><div>Diastereo- and enantioselective Mannich reactions of substituted pyruvates or α-ketoester derivatives that are larger than 2-oxopropanoates catalyzed by a tertiary amine derivative bearing functional groups that can form hydrogen bonds are described. γ-Amino β-substituted α-ketoesters were obtained with high diastereo- and enantioselectivities. Whereas substituted pyruvates did not react with imines in the presence of the catalyst system composed of a primary amine derivative and an acid that was previously used for the catalysis of Mannich reactions of ethyl pyruvate via the formation of an enamine, the use of the tertiary amine derivative bearing functional groups that can form hydrogen bonds enabled the activation of substituted pyruvates, leading to the formation of the desired Mannich reaction products.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155514"},"PeriodicalIF":1.5,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143487928","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Three new alkaloids from Corydalis saxicola and their antiproliferative activity 三种新的延胡索生物碱及其抗增殖活性
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-22 DOI: 10.1016/j.tetlet.2025.155513
Mei-Shan Li , Li Luo , Gang Wei , Xi-Xi Song , Hai-Ying Luo , Heng-Shan Wang , Jia-Zi Luo
{"title":"Three new alkaloids from Corydalis saxicola and their antiproliferative activity","authors":"Mei-Shan Li ,&nbsp;Li Luo ,&nbsp;Gang Wei ,&nbsp;Xi-Xi Song ,&nbsp;Hai-Ying Luo ,&nbsp;Heng-Shan Wang ,&nbsp;Jia-Zi Luo","doi":"10.1016/j.tetlet.2025.155513","DOIUrl":"10.1016/j.tetlet.2025.155513","url":null,"abstract":"<div><div>Three undescribed protoberberine alkaloids, named corydalisine L-N, along with four known compounds, were isolated from <em>Corydalis saxicola</em>. Their structures were accurately characterized using nuclear magnetic resonance (NMR) and mass spectrometry (MS). The absolute configurations were determined through the calculation of electronic circular dichroism (ECD). Compounds 1–3 were relatively rare 8,13-dicarbonyl protoberbine alkaloids, which are uncommon in plants of the genus Corydalis. All compounds were evaluated for their cytotoxicity against four human cancer cell lines.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155513"},"PeriodicalIF":1.5,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507958","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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