Synthetic Communications最新文献

{"title":"Synthesis of aromatic aldehydes via silver(I)-catalyzed formylation of aryl bromides in DMF promoted by samarium metal in air","authors":"Aowen Li ,&nbsp;Hongping Chen ,&nbsp;Mingzhong Mi ,&nbsp;Chao Wang ,&nbsp;Yan Qi ,&nbsp;Yongjun Liu","doi":"10.1080/00397911.2024.2364845","DOIUrl":"10.1080/00397911.2024.2364845","url":null,"abstract":"<div><p>Under ambient temperature conditions, a novel method has been developed for the conversion of aryl bromides to aromatic aldehydes, utilizing DMF (N,N-dimethylformamide) as both the starting material and solvent, in the presence of samarium metal and a trace of silver salts. This research has successfully explored an efficient approach for Barbier-type addition reactions, leading to the establishment of a novel C-C bond. A variety of bromides have been investigated as substrates, and aldehydes are readily obtained in moderate to high yields under mild conditions. The presence of 1 mol% of silver nitrate and potassium iodide is sufficient to catalyze the reaction, with the primary role of potassium iodide being to generate soluble silver iodide in the organic solvent, thereby catalyzing the reaction. The mechanism of the silver(I)-catalyzed process is discussed.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1060-1067"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141356822","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":"C1 − H morpholinomethylation and formylation of pyrrolo[1,2-a]quinoxalines","authors":"Thuy T. Ca ,&nbsp;Son N. T. Phan ,&nbsp;Tung T. Nguyen","doi":"10.1080/00397911.2024.2361024","DOIUrl":"https://doi.org/10.1080/00397911.2024.2361024","url":null,"abstract":"<div><p>We report two methods for selective morpholinomethylation and formylation of C1 − H bonds in pyrrolo[1,2-<em>a</em>]quinoxalines. Reaction of pyrrolo[1,2-<em>a</em>]quinoxalines and morpholine using CuI catalyst, (bis(trifluoroacetoxy)iodo)benzene oxidant, and DMSO solvent yielded the morpholinomethylation products. Meanwhile, formylation of C1 − H bonds in pyrrolo[1,2-<em>a</em>]quinoxalines progressed in the presence of CuI catalyst, trifluoroacetic acid, and DMSO solvent. Compounds bearing halogen, methylsulfonyl, pyridine, and thiophene groups were isolated in moderate yields.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 12","pages":"Pages 953-961"},"PeriodicalIF":2.1,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141308172","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":"Preparation and InhA inhibitory properties of novel dehydroacetic acid-derived thiazoles","authors":"Maamar Derdour ,&nbsp;Zehor Belkacem ,&nbsp;Nadji Belkheiri ,&nbsp;Salah Karef ,&nbsp;Mohamed Amari ,&nbsp;Nathalie Saffon-Merceron ,&nbsp;Frédéric Rodriguez ,&nbsp;Christian Lherbet ,&nbsp;Mokhtar Fodili ,&nbsp;Pascal Hoffmann","doi":"10.1080/00397911.2024.2361790","DOIUrl":"https://doi.org/10.1080/00397911.2024.2361790","url":null,"abstract":"<div><p>A series of 4-hydroxy-6-methyl-3-(1-(4-(aryl/methyl)thiazol-2-yl)-1<em>H</em>-pyrazol-3-yl)-2<em>H</em>-pyran-2-ones <strong>3a–h</strong> have been synthesized from aryl/methyl halomethylketones and a key pyrazole intermediate <strong>1</strong> using a convenient one-pot synthesis method. All compounds were characterized by NMR and MS, and the structure of three of them (<strong>3a</strong>, <strong>3b</strong> and <strong>3f</strong>) was resolved by X-ray diffraction. These heteroatom-rich thiazole compounds were then evaluated as inhibitors of <em>Mycobacterium tuberculosis</em> InhA, a key enzyme involved in the type II fatty acid biosynthesis pathway of the mycobacterium. Although inhibitory activities were found to be rather weak, molecular docking studies were also been carried out to understand a possible mode of interaction with key residues in the enzyme’s active site.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 12","pages":"Pages 962-972"},"PeriodicalIF":2.1,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141308173","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 carbohydrate polymers as a catalyst for organic synthesis: An update","authors":"Azzeddine Taoufyk ,&nbsp;Khaoula Oudghiri ,&nbsp;Moha Taourirte ,&nbsp;Mahfoud Agunaou ,&nbsp;Lahoucine Bahsis","doi":"10.1080/00397911.2024.2337090","DOIUrl":"10.1080/00397911.2024.2337090","url":null,"abstract":"<div><p>The biocompatibility, specificity, and consistency of natural carbohydrate polymers in catalyzing organic processes have garnered significant interest. For the production of organic compounds, a variety of carbohydrate polymers have been employed as heterogeneous catalysts, including agarose, cellulose, chitosan, chitin, sodium alginate, carrageenan, dextrin, starch, and pectin. This article provides an overview of several straightforward and efficient techniques for the mild reaction conditions catalytic synthesis of organic compounds employing carbohydrate polymers as the source of heterogeneous catalytic species.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 11","pages":"Pages 853-880"},"PeriodicalIF":2.1,"publicationDate":"2024-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140568844","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":"Rare demethylation of 4-benzylidene-2-phenyloxazolone","authors":"Maokai Jiang ,&nbsp;Yuankun Wang ,&nbsp;Yumeng Zhuang ,&nbsp;Xianzhang Wang ,&nbsp;Lei Yao","doi":"10.1080/00397911.2024.2349915","DOIUrl":"10.1080/00397911.2024.2349915","url":null,"abstract":"<div><p>This study presents a novel and rare demethylation of 4-benzylidene-2-phenyloxazolones under NaOH/EtOH/H₂O conditions. The potential mechanism underlying the phenomenon was evaluated through control reactions.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 11","pages":"Pages 909-917"},"PeriodicalIF":2.1,"publicationDate":"2024-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140994137","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":"Concise Synthesis of (-)-isoaltholactone and (±)-5-epi-OBn-Goniotriol","authors":"Yu-Jang Li ,&nbsp;Cheng-Chiao Li ,&nbsp;Chung-Chien Hou","doi":"10.1080/00397911.2024.2355474","DOIUrl":"10.1080/00397911.2024.2355474","url":null,"abstract":"<div><p>Concise route for the synthesis of (-)-isoaltholactone and (±)-5-<em>epi</em>-OBn-Goniotriol were described. Key features for the (-)-isoaltholactone synthesis involved; a) diastereoselective and enantioselective aldol reaction between chiral pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde afforded highly stereoselective <em>syn δ</em>-lactone, b) allylic 1,3-strain controlled epoxidation of styryl alkene following the stereospecific opening of the epoxide assisted by a proximal benzyloxy group completed the synthesis. Reaction of simple pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde gave <em>anti δ</em>-lactone. Epoxidation and epoxide opening of the styryl alkene substrate of <em>anti δ</em>-lactone derivative was also investigated, which led to the synthesis of (±)-5-<em>epi</em>-OBn-Goniotriol.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 11","pages":"Pages 918-926"},"PeriodicalIF":2.1,"publicationDate":"2024-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141123607","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":"Ultrasound-assisted synthesis of novel Schiff bases from 3-(2-oxo-2H-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole-4-carboxaldehyde and their cytotoxicity, apoptosis, cell cycle, molecular docking, and ADMET profiling","authors":"Mohammed A. Assiri ,&nbsp;Tarik E. Ali ,&nbsp;Ayat K. Alsolimani ,&nbsp;Ali A. Shati ,&nbsp;Mohammad Y. Alfaifi ,&nbsp;Serag E. I. Elbehairi","doi":"10.1080/00397911.2024.2347501","DOIUrl":"10.1080/00397911.2024.2347501","url":null,"abstract":"<div><p>With the ultimate goal of discovering new anticancer agents, this study involved the design and synthesis of fifteen novel Schiff bases <strong>4a</strong>,<strong>b</strong>, <strong>5</strong>, <strong>6a–d</strong>, <strong>7a–e</strong>, and <strong>8–10</strong> which contain 3-(2-oxo-2<em>H</em>-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1<em>H</em>-pyrazole moiety. The synthetic method depended on reaction of 3-(2-oxo-2<em>H</em>-chromen-3-yl)-1-(4-phenylthiazol-2-yl)-1<em>H</em>-pyrazole-4-carboxaldehyde (<strong>3</strong>) with a series of aromatic and heteroaryl amines under ultrasound irradiation to explore the influence of aromatic and heteroaryl rings on biological activity. The chemical structures of these Schiff bases were fully elucidated using various spectral and elemental analyses. The antiproliferative activities of the Schiff bases were studied by the standard SRB method. Among the new 15 Schiff bases, derivatives <strong>4a</strong>,<strong>b</strong>, <strong>5</strong>, and <strong>7b</strong> have significant cytotoxic effects against PC3, HepG2, and HCT116 cancer cell lines. These four bioactive Schiff bases significantly increased the late apoptosis of all studied tumor cells. Also, both products <strong>4a</strong> and <strong>4b</strong> arrested the cell cycle at the G1 phase, while both compounds <strong>5</strong> and <strong>7b</strong> arrested the S and G2 phases against PC3 cells. In addition, the products <strong>4a</strong>, <strong>4b</strong>, <strong>5</strong>, and <strong>7b</strong> have promising high abilities to arrest the cell cycle at the G2 phase against HepG2 and HCT116 cells. The different substitutions on the aryl ring were the basis for the structure–activity relationship study. The molecular docking study confirmed good binding interactions of these compounds with Cyclin-dependent kinase 8 (CDK-8) receptor, while the absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction supported that these bioactive products can be promising anticancer agents.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 11","pages":"Pages 881-908"},"PeriodicalIF":2.1,"publicationDate":"2024-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140993252","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":"Facile access to benzofuran-based bis-stilbene for organic laser dyes","authors":"Ziyi Zheng ,&nbsp;Guangling Bian ,&nbsp;Ling Song","doi":"10.1080/00397911.2024.2356632","DOIUrl":"10.1080/00397911.2024.2356632","url":null,"abstract":"<div><p>A concise and efficient synthetic protocol for the synthesis of furan-based bis-stilbene derivatives (BPBFCz1) was described, which is a very promising organic laser dye. Starting with 4,4’-diethynylbiphenyl, BPBFCz1 was prepared with a total yield of 40% through a three-step classical reaction of Sonogashira Coupling, intramolecular cyclization of 2-alkynyl phenol, and Buchwald Hartwig cross-coupling. The crystal structure of BPBFCz1 was presented for the first time. The synthesis strategy was applied to the synthesis of other three materials with similar structure and the yields of 28.6–36.6% were obtained.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 11","pages":"Pages 927-934"},"PeriodicalIF":2.1,"publicationDate":"2024-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141117018","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":"An efficient synthesis of pyrazolylbarbiturates by three-component reaction between barbituric/thiobarbituric acid, aroylphenylhydrazones and arylglyoxals","authors":"Nasim Tajaddini ,&nbsp;Mohammad Anary-Abbasinejad","doi":"10.1080/00397911.2024.2356640","DOIUrl":"10.1080/00397911.2024.2356640","url":null,"abstract":"<div><p>An effective protocol for synthesis of some new pyrazolylbarbiturate derivatives is reported through a one-pot, three-component reaction between barbituric/thiobarbituric acid, aroylphenylhydrazones and arylglyoxal derivatives. All reactions were conducted in ethanol as solvent without using any catalyst and products were obtained by simple filtering of the precipitated solids in high yields. All products were characterized by ¹H and ¹³C NMR and IR spectral and elemental analysis data.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 12","pages":"Pages 1010-1016"},"PeriodicalIF":2.1,"publicationDate":"2024-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141279328","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":"Photo induced eosin-Y catalyzed synthesis and molecular docking studies of 5,5-diphenylimidazolidine-2,4-dione","authors":"Km Garima ,&nbsp;Rohit Kumar ,&nbsp;Vishal Srivastava ,&nbsp;Praveen Pratap Singh ,&nbsp;Pravin Kumar Singh","doi":"10.1080/00397911.2024.2358370","DOIUrl":"https://doi.org/10.1080/00397911.2024.2358370","url":null,"abstract":"<div><p>One-pot photo induced eosin-Y catalyzed, green approach for the synthesis of 5,5-diphenylimidazolidine-2,4-dione (Phenytoin) has been developed. The reaction proceeded smoothly, for a wide range of benzil and urea/thiourea derivatives as cheap and eco friendly reagents with high reactivity and good selectivity in DMSO as green solvent at room temperature in good to excellent yields. Biological studies such as drug-likeness and molecular docking have been conducted on the synthesized compounds, some of the compounds showed appreciable activity with least binding energy.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 12","pages":"Pages 1017-1029"},"PeriodicalIF":2.1,"publicationDate":"2024-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141308171","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}