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Reaction under Ball-Milling: Solvent- and Metal-Free One-Pot Diastereoselective Synthesis of Tetrahydroquinoline Derivatives as Potential Antibacterial and Anticancer Agents 球磨条件下的反应：作为潜在抗菌剂和抗癌剂的四氢喹啉衍生物的无溶剂和无金属单锅非对映选择性合成
IF 2 4区 化学
Synlett Pub Date : 2024-08-23 DOI: 10.1055/a-2378-1847
Keya Roy, Anay Saha, Suprakash Sahoo, Subhrajyoti Banerjee, Chitrangada Das Mukhopadhyay, Subhash Banerjee, Laksmikanta Adak
{"title":"Reaction under Ball-Milling: Solvent- and Metal-Free One-Pot Diastereoselective Synthesis of Tetrahydroquinoline Derivatives as Potential Antibacterial and Anticancer Agents","authors":"Keya Roy, Anay Saha, Suprakash Sahoo, Subhrajyoti Banerjee, Chitrangada Das Mukhopadhyay, Subhash Banerjee, Laksmikanta Adak","doi":"10.1055/a-2378-1847","DOIUrl":"https://doi.org/10.1055/a-2378-1847","url":null,"abstract":"<p>A mild and efficient one-pot, three-component ball-mill-assisted reaction of aldehydes, anilines, and dihydrofuran (or dihydropyran and cyclohexenone) has been described for the first time in the presence of the catalytic amount of aqueous perchloric acid (8 mol%) at room temperature under organic solvent- and metal-free conditions. The reactions are fast (1 h), providing the products with excellent yields and high diastereoselectivity. This procedure endows a simple, efficient, and cost-effective method for the diastereoselective synthesis of furano- and pyrano-tetrahydroquinolines and phenanthridinone derivatives, which are important biological compounds. The diastereomers with <i>cis</i> configuration were isolated as major products. The H–H COSY, NOESY experiments and X-ray crystallographic analysis of selected compounds were performed to confirm the <i>cis</i> isomer. The synthesized tetrahydroquinolines have been evaluated <i>in vitro</i> for their antibacterial and anticancer activities, and it was found that both the prepared compounds showed significant antibacterial and anticancer properties.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"22 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210308","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
Cobalt(II)-Catalyzed Proficient Synthesis of Enaminones from Aryl Alkenes and Amines 钴(II)催化的芳基烯烃和胺烯酮的高效合成
IF 2 4区 化学
Synlett Pub Date : 2024-08-22 DOI: 10.1055/a-2377-0230
Subham Sau, Krishna Mohan Das, Swapnamoy Ghosh, Arunabha Thakur
{"title":"Cobalt(II)-Catalyzed Proficient Synthesis of Enaminones from Aryl Alkenes and Amines","authors":"Subham Sau, Krishna Mohan Das, Swapnamoy Ghosh, Arunabha Thakur","doi":"10.1055/a-2377-0230","DOIUrl":"https://doi.org/10.1055/a-2377-0230","url":null,"abstract":"<p>A simple, cost-effective, and modular strategy has been developed to synthesize synthetically and pharmaceutically active enaminones by oxidative amination of aryl alkenes with amines and CHCl<sub>3</sub>, using <i>tert</i>-butyl hydroperoxide as an oxidant. We describe the synthesis of enaminones from vinyl arenes and sterically hindered <i>N</i>,<i>N</i>-diisopropylethylamine (DIPEA) by employing an Earth-abundant cobalt salt as a catalyst within a very short reaction period for the first time. Furthermore, nitrogen- and oxygen-containing heterocyclic compounds have been synthesized from these highly functionalized enaminones. Moreover, various control experiments, such as radical trapping reaction, along with a Hammett analysis with various types of substituents on the styrene ring unraveled the detailed mechanism of this reaction pathway.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"10 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210309","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 the (±)-trans-Whiskey and Cognac Lactones via a Donor–Acceptor Cyclopropane Hemimalonate 通过供体-受体环丙烷半马来酸酯合成 (±)-trans-Whiskey 和 Cognac 内酯
IF 2 4区 化学
Synlett Pub Date : 2024-08-22 DOI: 10.1055/s-0043-1775397
Tim J. Menna, Michael A. Kerr
{"title":"Synthesis of the (±)-trans-Whiskey and Cognac Lactones via a Donor–Acceptor Cyclopropane Hemimalonate","authors":"Tim J. Menna, Michael A. Kerr","doi":"10.1055/s-0043-1775397","DOIUrl":"https://doi.org/10.1055/s-0043-1775397","url":null,"abstract":"<p>Aging alcohol is a timeless process that has seen little variation since the time of its invention. Molecules stored within the wood can be extracted by the alcohol to produce unique flavors. Among these molecules exist the whiskey and cognac lactones. Herein we report a short synthesis of the <i>trans</i>-whiskey and cognac lactones using a rearrangement of cyclopropane hemimalonates.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"459 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142226725","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
Hypervalent-Iodine-Mediated Base-Free Oxidative Olefination of Benzylic Amines to Access α,β-Unsaturated Ketones 高价碘介导的苄胺无碱氧化烯化反应，以获得 α,β-不饱和酮体
IF 2 4区 化学
Synlett Pub Date : 2024-08-22 DOI: 10.1055/s-0043-1775392
Bapurao D. Rupanawar, Ajay H. Bansode, Gurunath Suryavanshi
{"title":"Hypervalent-Iodine-Mediated Base-Free Oxidative Olefination of Benzylic Amines to Access α,β-Unsaturated Ketones","authors":"Bapurao D. Rupanawar, Ajay H. Bansode, Gurunath Suryavanshi","doi":"10.1055/s-0043-1775392","DOIUrl":"https://doi.org/10.1055/s-0043-1775392","url":null,"abstract":"<p>We report a one-pot base-free protocol for the oxidative olefination of benzylic amines promoted by a hypervalent iodine reagent for the synthesis of α,β-unsaturated ketones. Mechanistically, (diacetoxyiodo)benzene oxidizes the benzylic amine to the corresponding imine, which, on reaction with a phenacyl(triphenyl)phosphonium bromide salt and an in situ generated acetoxy anion leads to an α,β-unsaturated ketone. A wide range of α,β-unsaturated ketones were easily accessed through direct oxidative olefination of substituted benzylic amines in good to excellent yields and with high <i>E</i>-selectivity.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"24 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210311","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
Chiral-Bisphosphine-Catalyzed Asymmetric Staudinger/Aza-Wittig Reaction: Development, Mechanism Study, and Synthetic Application 手性双膦催化的不对称施陶丁格/阿扎-维蒂希反应：开发、机理研究和合成应用
IF 2 4区 化学
Synlett Pub Date : 2024-08-22 DOI: 10.1055/s-0043-1775038
Hongzhi Yang, Truc Quynh Nguyen, Yefeng Tang
{"title":"Chiral-Bisphosphine-Catalyzed Asymmetric Staudinger/Aza-Wittig Reaction: Development, Mechanism Study, and Synthetic Application","authors":"Hongzhi Yang, Truc Quynh Nguyen, Yefeng Tang","doi":"10.1055/s-0043-1775038","DOIUrl":"https://doi.org/10.1055/s-0043-1775038","url":null,"abstract":"<p>The enantioselective desymmetrization of 2,2-disubstituted cyclohexane-1,3-diones has been realized through an unprecedented chiral-bisphosphine-catalyzed asymmetric Staudinger/aza-Wittig reaction. The key to this work’s success lies in utilizing an electronically rich and sterically hindered chiral bisphosphine reagent, namely DuanPhos, as a catalyst. In addition, a unique reductive system was established to address the requisite P<sup>III/PV</sup> = O redox cycle. The mechanism of the chiral-bisphosphine-catalyzed asymmetric Staudinger/aza-Wittig reaction has been elucidated through combined computational and experimental studies. Several crinine-type amaryllidaceae alkaloids have been synthesized concisely, hinging on the newly developed methodology.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"263 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210312","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
Enantioselective Oxidative Homocoupling of 2-Oxindoles with a Chiral Bisguanidinium Hypoiodite Catalyst 用手性次碘酸双胍催化剂对 2-氧化吲哚进行对映选择性氧化偶联反应
IF 2 4区 化学
Synlett Pub Date : 2024-08-20 DOI: 10.1055/s-0043-1775056
Minami Odagi, Yuta Shimizu, Kota Sugimoto, Io Mori, Ban Xu, Choon Hong Tan, Kazuo Nagasawa
{"title":"Enantioselective Oxidative Homocoupling of 2-Oxindoles with a Chiral Bisguanidinium Hypoiodite Catalyst","authors":"Minami Odagi, Yuta Shimizu, Kota Sugimoto, Io Mori, Ban Xu, Choon Hong Tan, Kazuo Nagasawa","doi":"10.1055/s-0043-1775056","DOIUrl":"https://doi.org/10.1055/s-0043-1775056","url":null,"abstract":"<p>The bisoxindole motif is present in a variety of biologically active compounds. Here, we report an enantioselective oxidative homocoupling reaction of 2-oxindoles in the presence of a chiral bisguanidinium hypoiodite catalyst, providing access to the corresponding optically active bisoxindoles in excellent yields and with moderate to high diastereo- and enantioselectivities.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"10 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210265","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
Thiuram Disulfide Mediated Copper-Catalyzed C–S Cross-Coupling: Synthesis of S-Thiocarbamate Compounds 二硫化秋兰姆介导的铜催化 C-S 交叉偶联：S-Thiocarbamate 化合物的合成
IF 2 4区 化学
Synlett Pub Date : 2024-08-19 DOI: 10.1055/a-2375-7696
Sourav Mondal, Debabrata Patra, Amit Saha
{"title":"Thiuram Disulfide Mediated Copper-Catalyzed C–S Cross-Coupling: Synthesis of S-Thiocarbamate Compounds","authors":"Sourav Mondal, Debabrata Patra, Amit Saha","doi":"10.1055/a-2375-7696","DOIUrl":"https://doi.org/10.1055/a-2375-7696","url":null,"abstract":"<p>Thiuram disulfides undergo a Cu(I)-catalyzed C–S cross-coupling with aryl iodides through Cu(OAc)<sub>2</sub>·H<sub>2</sub>O-assisted desulfurization to produce the <i>S</i>-thiocarbamate ester compounds efficiently. Various aryl iodides containing diverse substituents underwent a smooth reaction with a series of cyclic and acyclic secondary amine-based thiuram disulfides under an open-air atmosphere. A probable mechanistic pathway has been suggested based on control experiments and reports from the literature.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"10 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210313","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
1,2-Diaroyl Benzofurans: Synthesis and Photochromic Properties 1,2-二芳基苯并呋喃：合成与光致变色特性
IF 2 4区 化学
Synlett Pub Date : 2024-08-15 DOI: 10.1055/s-0043-1775039
Jianming Zhong, Shuangshuang Li, Zhaoxin Wang, Wang Zhou
{"title":"1,2-Diaroyl Benzofurans: Synthesis and Photochromic Properties","authors":"Jianming Zhong, Shuangshuang Li, Zhaoxin Wang, Wang Zhou","doi":"10.1055/s-0043-1775039","DOIUrl":"https://doi.org/10.1055/s-0043-1775039","url":null,"abstract":"<p>A cascade reaction involving a base-promoted nucleophilic substitution reaction between diketones and α-bromoacetophenone derivatives and the subsequent selective condensation–cyclization was developed for the synthesis of 1,2-diaroyl benzofurans. 1,2-Diaroyl benzofurans with different functional groups and structures exhibit reversible photochromic behaviors in solution, solid state, and thin films with diverse colors, demonstrating a potential application in the field of optical functional materials.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"4 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210314","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
Ketocalixarenes: Versatile yet still Unexplored Macrocycles 酮钙烯烃：用途广泛但仍未开发的大环
IF 2 4区 化学
Synlett Pub Date : 2024-08-12 DOI: 10.1055/s-0043-1775380
Ori Shalev, Silvio E. Biali
{"title":"Ketocalixarenes: Versatile yet still Unexplored Macrocycles","authors":"Ori Shalev, Silvio E. Biali","doi":"10.1055/s-0043-1775380","DOIUrl":"https://doi.org/10.1055/s-0043-1775380","url":null,"abstract":"<p>Ketocalix[<i>n</i>]arenes can be prepared via oxidation of the methylene groups of protected calix[<i>n</i>]arenes. The presence of carbonyl groups at the bridges alters the preferred conformation and reactivity of the macrocycle and provides an entry point (via nucleophilic additions reactions) to a wide array of methylene-substituted derivatives as well as calix[<i>n</i>]radialenes.</p> <p>1\tIntroduction</p> <p>2 Synthesis of Ketocalix[<i>n</i>]arenes</p> <p>2.1 Ketocalix[4]arene Derivatives</p> <p>2.2 Systems Possessing both Carbonyl and Bromomethane Bridges</p> <p>2.3 Pentaoxoketocalix[5]arene and Hexaoxoketocalix[6]arene Derivatives</p> <p>2.4 Monooxo- and Dioxoketocalix[6]arenes</p> <p>3 Conformation of Ketocalixarenes</p> <p>4 Reactions of Ketocalixarenes</p> <p>4.1 Alkylation of the OH Groups</p> <p>4.2 Intramolecular Aromatic Nucleophilic Substitution</p> <p>4.3 Reduction of the Carbonyl Groups</p> <p>4.4 Reaction of <b>5c</b> with PhLi</p> <p>4.5 Reaction with <i>tert</i>-Butyllithium</p> <p>5 From Ketocalix[<i>n</i>]arenes to Calix[<i>n</i>]radialenes and Calix[<i>n</i>]rotanes</p> <p>6 Summary and Outlook</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"28 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142210151","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 and Biological Evaluation of Novel Coumarin Derivatives Bearing a Sulfonamide Moiety as Antiviral and Antibacterial Agent 含磺酰胺分子的新型香豆素衍生物作为抗病毒和抗菌剂的合成与生物学评价
IF 2 4区 化学
Synlett Pub Date : 2024-07-22 DOI: 10.1055/a-2361-6916
Song Bai, Lin Liu, Rong Wu, Shouyin Tang, Suran Wan, Fang Wang, Xian Wei, Lijun Chen, Shunyi Xu, Miao Li
{"title":"Synthesis and Biological Evaluation of Novel Coumarin Derivatives Bearing a Sulfonamide Moiety as Antiviral and Antibacterial Agent","authors":"Song Bai, Lin Liu, Rong Wu, Shouyin Tang, Suran Wan, Fang Wang, Xian Wei, Lijun Chen, Shunyi Xu, Miao Li","doi":"10.1055/a-2361-6916","DOIUrl":"https://doi.org/10.1055/a-2361-6916","url":null,"abstract":"<p>Twenty novel 4-bromocoumarin derivatives bearing a sulfonamide moiety were designed and synthesized. Their antiviral and antibacterial activities were systematically evaluated. The test results show that all the target compounds possess moderate to excellent antiviral and antibacterial activities. Among all target compounds, one compound exhibited good antiviral activity against TMV, CMV, and PVY, which is superior to ribavirin. Moreover, two target compounds exhibited good <i>in vitro</i> antibacterial activity against <i>Psa</i>, with an EC<sub>50</sub> value of 44.9 mg/L and 49.3 mg/L, respectively, which were better than thiodiazole copper and zinc thiazole, with an EC<sub>50</sub> value of 56.3 mg/L and 50.2 mg/L, respectively. The results provide insights for the development of multifunctional pesticides.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"41 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141785355","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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