Haiyan Xu , Yuanyuan Huang , Yinchun Liang , Nan Wang , Dejun Dong , Mengke Wang , Weichun Huang , You Zi , Zhanping Yang
{"title":"Photochemical oxidative coupling of thiols to disulfides using Bi quantum dots: Mild and efficient catalysis","authors":"Haiyan Xu , Yuanyuan Huang , Yinchun Liang , Nan Wang , Dejun Dong , Mengke Wang , Weichun Huang , You Zi , Zhanping Yang","doi":"10.1080/00397911.2024.2392187","DOIUrl":"10.1080/00397911.2024.2392187","url":null,"abstract":"<div><p>Herein, we present an efficient synthesis method utilizing Bi quantum dots (QDs) as catalysts for the photochemical oxidative coupling of thiols to disulfides under mild conditions. The protocol offers low catalyst loading, simplicity in reaction setup as well as high efficiency. Aromatic thiols and aliphatic thiols are successfully transformed into disulfides with good to quantitative yields, demonstrating tolerance to various substituents and heterocycles. Additionally, the protocol extends to the synthesis of asymmetric disulfides and allows for gram-scale synthesis.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 17","pages":"Pages 1482-1493"},"PeriodicalIF":1.8,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142089312","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}
Nai-Xing Wang , Zhan Yan , Lei-Yang Zhang , Dumitra Lucan
{"title":"Some fluorine-containing and sulfur-containing functional new reagents","authors":"Nai-Xing Wang , Zhan Yan , Lei-Yang Zhang , Dumitra Lucan","doi":"10.1080/00397911.2024.2390697","DOIUrl":"10.1080/00397911.2024.2390697","url":null,"abstract":"<div><div>The research and development of new reagents play a crucial role for organic synthesis. In recent years, numerous new reagents with universal applicability have been reported. Recent research progress of selected fluorine-containing and sulfur-containing new reagents for difluoromethylation, trifluoromethylation and thiotrifluoromethylation are summarized. Additionally, some sulfur-containing new reagents are provided, as sulfur-containing reagent, Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub>-<em>t</em>-butylhydroperoxide (TBHP) is a new reagent for selective oxidation of aromatic alcohols to aldehydes.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 21","pages":"Pages 1785-1807"},"PeriodicalIF":1.8,"publicationDate":"2024-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216249","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}
Xiaoli Jia , Yindi Fan , Tong Chen , Yuxin Li , Yueyu Zhang , Sanhu Zhao
{"title":"Functional ionic liquids based on DABCO: Efficient catalysts for chemical fixation of CO2 into cyclic carbonates","authors":"Xiaoli Jia , Yindi Fan , Tong Chen , Yuxin Li , Yueyu Zhang , Sanhu Zhao","doi":"10.1080/00397911.2024.2394089","DOIUrl":"10.1080/00397911.2024.2394089","url":null,"abstract":"<div><p>A series of basic functional ionic liquids were prepared from 1, 4-diazabicyclo [2.2.2] octane (DABCO) with various halogenated hydrocarbons, then these functional ionic liquids were used as catalysts for the chemical fixation of CO<sub>2</sub> into cyclic carbonates and the influence of the structure of the ionic liquids was investigated. The results showed that the N atom active center, types of anions and hydrogen bond of the catalyst play a key role in the cycloaddition reaction of CO<sub>2</sub> with epoxides to cyclic carbonates. Under mild reaction conditions (T = 100 °C, 1 atm CO<sub>2</sub>), the ionic liquid [DABCO-CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH] I showed the best catalytic effect, which has notable advantages such as high catalytic activity, eco-friendly, ease of work-up and convenient reuse.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 17","pages":"Pages 1450-1461"},"PeriodicalIF":1.8,"publicationDate":"2024-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142089309","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}
{"title":"Recent advances in the synthesis of phosphoramidate derivatives: A comprehensive review and analysis","authors":"Djenet Amel Dehmchi , Fouzia Bouchareb , Malika Berredjem","doi":"10.1080/00397911.2024.2391917","DOIUrl":"10.1080/00397911.2024.2391917","url":null,"abstract":"<div><div>Organophosphorus compounds (OPs) are a diverse group of chemical compounds that contain organic moieties directly bonded to phosphorus or through a heteroatom like oxygen, nitrogen, or sulfur. They are ubiquitous in the human environment due to their unique properties and high biological activity. OPs have been widely used in various fields such as agriculture (as pesticides), industry (for producing lubricants, hydraulic fluids, and plastics), medicine (as drugs against osteoporosis, anticancer, and antiviral compounds), and veterinary (as anthelmintics). As an important class of organophosphorus compounds, this review provides an overview of phosphoramidate compounds covering their synthetic pathways, a brief explanation of their mechanisms, and their various applications.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 22","pages":"Pages 1909-1939"},"PeriodicalIF":1.8,"publicationDate":"2024-08-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216150","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}
{"title":"Applications of 4-alkynylated pyrazol-3-ones: Synthesis of pyrazol-4-yl furan- and/or thiophene-2-carboxylates","authors":"Takafumi Fujita , Fumi Okabe-Nakahara , Hiroshi Maruoka , Eiichi Masumoto","doi":"10.1080/00397911.2024.2385539","DOIUrl":"10.1080/00397911.2024.2385539","url":null,"abstract":"<div><p>Chemical reactivity and applications of 4-alkynylated pyrazol-3-ones are described. A facile access to the synthesis of novel pyrazol-4-yl furan- and/or thiophene-2-carboxylates through the ring transformation and subsequent acylation of 4-alkynylated pyrazol-3-ones as the key intermediates, which were prepared from pyrazole-4,5-dione and terminal alkynes, in moderate to good yields is achieved. All the synthesized compounds were characterized by spectroscopic analysis.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1321-1331"},"PeriodicalIF":1.8,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141883139","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}
{"title":"Synthesis and evaluation of isoxazole derivatives of lapachol as inhibitors of pyruvate kinase M2","authors":"Deepak Mali , Barkha Darra Wadhwani , Vandana Nunia , Kavita Joshi , Rashmy Nair , Tarun Kumar , Poonam Khandelwal","doi":"10.1080/00397911.2024.2383952","DOIUrl":"10.1080/00397911.2024.2383952","url":null,"abstract":"<div><p>Lapachol is a proven anticancer medication ingredient that has been removed from the market due to its toxicity, but cannot disregard its therapeutic properties. Aiming to search for potent anticancer derivative of lapachol with a harmless impact, a series of novel isoxazoles derivatives were synthesized by its chemical modification. Alkylation of the hydroxyl group of lapachol gave its propargyl ether which, <em>via</em> copper-catalyzed cycloaddition (CuAAC) click chemistry with different oximes, afforded naphthoquinonolyl isoxazole derivatives. Molecular docking study of lapachol and its newly synthesized derivatives was also performed for potential inhibitory action toward PKM2 enzyme. All compounds showed good docking results. Among these synthesized lapachol derivatives, compound <strong>7c</strong> showed the highest binding affinity and followed all drug rules. These findings indicated that the introduction of isoxazole fragment to the lapachol may have a significant impact on pyruvate levels in cancer cells and provides further directions for future research to find new lapachol analogues suitable for cancer treatment.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1311-1320"},"PeriodicalIF":1.8,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141883161","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}
Ashraf A. Sediek , Asmaa F. Kassem , Mohamed S. Abdel-Aziz , Ahmed Younis
{"title":"Synthesis, antimicrobial activity, and biofilm inhibition studies of 1,2,3-triazole-containing 2,3-dihydrothiazole","authors":"Ashraf A. Sediek , Asmaa F. Kassem , Mohamed S. Abdel-Aziz , Ahmed Younis","doi":"10.1080/00397911.2024.2387121","DOIUrl":"10.1080/00397911.2024.2387121","url":null,"abstract":"<div><p>The newly synthesized 1,2,3-triazole-thiazole hybrids were first evaluated for their antimicrobial activity against different microbial strains. Most of it showed a marked selectivity against Gram-positive and Gram-negative bacterial strains. The MIC assay was then assessed; for <em>S. aureus</em>, <strong>4a</strong> was equipotent to the reference neomycin, while <strong>3a</strong>, <strong>3b</strong>, and <strong>8b</strong> were 2-fold lower. For <em>E. coli</em>, compounds <strong>3a</strong>, <strong>4a</strong>, and <strong>8c</strong> were equipotent to neomycin, while <strong>5a</strong> was 8-fold higher, and <strong>8d</strong> was 2-fold higher. Most of tested compounds showed superiority to the reference drug against <em>C. albicans</em>; <strong>8a</strong> and <strong>8e</strong> showed MIC value of 16-fold higher than neomycin, while <strong>3a</strong> was 8-fold higher. Also, <strong>3b</strong> and <strong>8f</strong> were 4-fold higher; <strong>8d</strong> was 2-fold higher, while <strong>5a</strong> was equipotent to neomycin against the same microbe. Further biofilm formation inhibition assay was conducted to the most active compounds, <strong>5a</strong> was the most active against the three types of bacterial strains.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1376-1387"},"PeriodicalIF":1.8,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141923582","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}
Dharti R. Bhandari , Urvi J. Khengar , Rajesh H. Vekariya , Jinal A. Gajjar
{"title":"Recent advances in meglumine catalyzed organic synthesis: A comprehensive review","authors":"Dharti R. Bhandari , Urvi J. Khengar , Rajesh H. Vekariya , Jinal A. Gajjar","doi":"10.1080/00397911.2024.2380062","DOIUrl":"10.1080/00397911.2024.2380062","url":null,"abstract":"<div><p>Meglumine, an amino sugar alcohol compound, has recently emerged as a promising catalyst in various organic transformations due to its unique properties. This review provides a comprehensive overview of the applications of meglumine catalyst in organic synthesis, highlighting their efficiency, versatility, and mechanistic insights. Key examples of reactions catalyzed by meglumine, including aldol condensation, Michael addition, Mannich reaction, and other one-pot multicomponent condensation reaction are discussed along with mechanistic pathways and synthetic strategies. Additionally, recent advancements and future perspectives in the field are explored.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1285-1310"},"PeriodicalIF":1.8,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141883097","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}
Zeinab A. Abdallah , Redhab A. J. Alfraiji , Fawzy A. Attaby , Mohamed S. Mohamed Ahmed
{"title":"Synthesis, in vitro-antimicrobial investigation, molecular docking, and DFT studies of novel bis-thiazole derivatives","authors":"Zeinab A. Abdallah , Redhab A. J. Alfraiji , Fawzy A. Attaby , Mohamed S. Mohamed Ahmed","doi":"10.1080/00397911.2024.2387124","DOIUrl":"10.1080/00397911.2024.2387124","url":null,"abstract":"<div><p>Two series of bis-thiazole derivatives (<strong>7a–f</strong> and <strong>9a–j</strong>) were synthesized efficiently <em>via</em> two steps. First, the condensation of 3,3’-(alkane-diylbis(oxy)) dibenzaldehyde (<strong>3a,b</strong>) with hydrazinecarbothioamide (<strong>4</strong>) affording 2,2’-(((alkane-1,2-diylbis(oxy))bis(3,1-phenylene))bis(methaneylylidene))bis(hydrazine-1-carbothioamide) (<strong>5a,b</strong>). The formed <strong>5a,b</strong> were then mixed with 2-bromo-1-arylethan-1-one <strong>6a–c</strong> affording the corresponding thiazole derivatives <strong>7a–f</strong>. Similarly, bis-thiazole derivatives <strong>9a–j</strong> were synthesized through heating bis(hydrazine-1-carbothioamides<strong>) 5a,b</strong> with 2-oxo-N-arylpropanehydrazonoyl chloride <strong>8a–i</strong>. Afterwards the synthesized bis-thiazoles <strong>7a–f</strong> and <strong>9a–j</strong> were evaluated for their in vitro-antibacterial activity against gram-positive and gram-negative bacterial strains. Among the tested candidates, compounds <strong>7a</strong>, <strong>7c</strong>, and <strong>7d</strong> exhibited the highest antibacterial activity. Furthermore, a docking analysis showed that the most promising biologically active candidates under investigation are joined to the same amino acid (acids) as references supporting the biological activity of the tested compounds toward both gram-positive bacteria-protein and gram-negative bacteria-protein. DFT calculations were carried out to gain a better understanding of the target bis-thiazole-structures and their assembly mechanism.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1388-1411"},"PeriodicalIF":1.8,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141924560","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}
{"title":"Hydrogen bond assisted reactivity of Ylidineketonitriles with 1° amines: A chemoselective synthesis of 2-pyridone and 2-aminopyridine derivatives","authors":"Damodar Karuturi , Mahesh Kalbagh , Prashantha Kamath , Venunath Hapse , Alok Kumar Pandey , Mark Montgomery , Mukul Lal","doi":"10.1080/00397911.2024.2385567","DOIUrl":"10.1080/00397911.2024.2385567","url":null,"abstract":"<div><p>Ylidineketonitrile <strong>2</strong> with chlorodifluoromethyl (A = Cl) demonstrated a strong solvent dependence reaction with primary amines to form either 1-<em>N</em>-alkylated-3,5-disubstituted-2-pyridones or 2-<em>N</em>-alkylated-3, 5-trisubstituted pyridines. The methodology was tested for its scope with primary amines and synthesized 29 derivatives in good to excellent yield. Ylidineketonitrile <strong>2e</strong> preferrentially forms pyridone derivatives in the majority of the solvents screened except trifluoroethanol, where chemoselective formation of 2-aminopyridine derivatives was observed.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 16","pages":"Pages 1344-1353"},"PeriodicalIF":1.8,"publicationDate":"2024-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141942789","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}