Sang Gyu Shin , Hyun-Woo Oh , Byung Chang Kim , Jaeseung Ok , Seung In Lee , Sung Pyo Youn , Hyun Hee Bae , Ji Yoon Park , Jin Woo Han , Chang Hoon Lee
{"title":"Synthesis of multifunctionalized allyl isothiocyanates via isomerization of Morita-Baylis-Hillman adduct-derived allylic thiocyanates","authors":"Sang Gyu Shin , Hyun-Woo Oh , Byung Chang Kim , Jaeseung Ok , Seung In Lee , Sung Pyo Youn , Hyun Hee Bae , Ji Yoon Park , Jin Woo Han , Chang Hoon Lee","doi":"10.1080/00397911.2024.2441336","DOIUrl":"10.1080/00397911.2024.2441336","url":null,"abstract":"<div><div>An efficient method to synthesize functionalized allyl isothiocyanates in moderate yields has been demonstrated, based on the isomerization of Morita-Baylis-Hillman adduct-derived allylic thiocyanates. This methodology offers obvious advantages such as easy purification, atom economy, and a broad scope of substrates.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 251-258"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097178","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":"Electrochemical Fe-catalyzed deoxygenative alkoxycarbonylation of imidazoheterocycles with carbazates","authors":"Jun-Qi Zhang , Hangfei Huang , Ying Fu","doi":"10.1080/00397911.2025.2458623","DOIUrl":"10.1080/00397911.2025.2458623","url":null,"abstract":"<div><div>Imidazo[1,2-a]pyridine derivatives possess widespread applications in the pharmaceutical industry and bioactive natural products. The diverse functionalization of this skeleton has attracted much attention from chemists. Herein, we reported an electrochemical deoxygenative alkoxycarbonylation of imidazoheterocycles by using electrons as the traceless oxidant under mild and oxidant-free conditions. Notably, our strategy provided a green and practical approach for introducing ester group into imidazo[1,2-a]pyridine derivatives by employing easily available and bench-stable carbazates as ester source.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 422-432"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377775","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":"Unlocking the imidazole ring: A comprehensive review of synthetic strategies","authors":"Peter Solo , M. Arockia Doss","doi":"10.1080/00397911.2024.2414201","DOIUrl":"10.1080/00397911.2024.2414201","url":null,"abstract":"<div><div>Imidazole, a five-membered heterocyclic compound, has multipurpose applications for its bioactivity, uses in charge transport materials, and NLO materials. The review provides a comprehensive survey of the synthetic strategies of imidazole from various starting materials, highlighting their percentage yield and mechanistic insights. The most popular starting materials for the syntheses of imidazole include diketones, cyanides, imines, amidines, imidamides, di-amines, and oximes. Although the selection of a particular synthetic strategy will depend largely on the desired imidazole derivative, the survey consists of more than a century of research on imidazole synthetic procedures, starting with Heinrich Debus synthesis in 1858 till the present day. Most recent advancements and future perspectives in the field have been explored. The study will help researchers choose the most suitable starting material, catalyst, solvent, or reaction conditions for the synthesis of various imidazole derivatives.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 3","pages":"Pages 183-235"},"PeriodicalIF":1.8,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143097179","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}
Jyothi Dhuguru , Brandon English , Ryan W. Dellinger , Marie E. Migaud
{"title":"Deprotection of nucleosides by lysine-assisted methanolysis of esters and amides","authors":"Jyothi Dhuguru , Brandon English , Ryan W. Dellinger , Marie E. Migaud","doi":"10.1080/00397911.2025.2456103","DOIUrl":"10.1080/00397911.2025.2456103","url":null,"abstract":"<div><div>A deacylation method was developed based on lysine-assisted methanolysis of nucleoside-derived esters and arylamides. The present methodology complements well-established deacylation methods, using a minimum molar equivalency of lysine and methanol under mild heating to generate the deacylated nucleoside and recyclable lysine and volatile methyl esters as byproducts. A variety of acylated canonical nucleosides and hydrolytically labile non-canonical nucleosides like nicotinamide riboside (NR) and its reduced form (NRH) were deprotected under such lysine-assisted conditions, demonstrating the versatility of this approach. Having determined this one-pot process’s <em>E</em>-factor and reaction mass index, we find this method greener than the more established deacylation processes.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 381-393"},"PeriodicalIF":1.8,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377774","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}
Chengkan Gao , Lin Li , Xiangyang Lin , Renming Pan , Wenfang Zheng
{"title":"Selectfluor-mediated oxidative deamination: A scalable approach to aromatic aldehydes synthesis","authors":"Chengkan Gao , Lin Li , Xiangyang Lin , Renming Pan , Wenfang Zheng","doi":"10.1080/00397911.2025.2458625","DOIUrl":"10.1080/00397911.2025.2458625","url":null,"abstract":"<div><div>The catalyst-free oxidative deamination without over-oxidation constitutes a considerable challenge in the synthesis of aromatic aldehydes. Herein, we introduce a Selectfluor-mediated Lewis acid system that achieves the oxidative deamination of benzylic amines with α-C-H bond activation to yield aromatic aldehydes. Noteworthy features include the direct use of Selectfluor that can activate the α-C-H bond under catalyst- and base-free conditions via the in-situ dehydrofluorination effect. The approach is demonstrated for a broad scope of benzylic amines without over-oxidation and accomplishes 200 mmol scale synthesis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 433-441"},"PeriodicalIF":1.8,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377776","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}
Vankayala Ramesh Babu , V. D. N. Kumar Abbaraju , Reddymasu Sreenivasulu , Dasari Sravani , Singamsetty Rangaswamy , Ravi Kumar Kapavarapu , Deva H.Puranam , Farha Farahim
{"title":"Design, synthesis, anticancer evaluation and molecular docking studies of different aryl derivatives of azaindole-pyrimidine-1,3,4-oxadiazoles","authors":"Vankayala Ramesh Babu , V. D. N. Kumar Abbaraju , Reddymasu Sreenivasulu , Dasari Sravani , Singamsetty Rangaswamy , Ravi Kumar Kapavarapu , Deva H.Puranam , Farha Farahim","doi":"10.1080/00397911.2025.2457440","DOIUrl":"10.1080/00397911.2025.2457440","url":null,"abstract":"<div><div>The aryl-azaindole-pyrimidine-1,3,4-oxadiazole derivatives (<strong>12a–j</strong>) were synthesized by Suzuki coupling reaction between bromo-azaindole-1,3,4-oxadiaole intermediate <strong>10</strong> and various aryl boronic acids (<strong>11a–j</strong>) by using of Pd(dppf)Cl<sub>2</sub> and K<sub>2</sub>CO<sub>3</sub> in 1,4-dioxane/H<sub>2</sub>O. Here, the Suzuki coupling mechanism starts with the oxidative addition followed by transmetallation and ends with reductive elimination. These derivatives were screened in vitro anticancer applications against four human cancer cell lines including MCF-7, A549, Colo-205, and A2780 by employing of MTT method, the well-known chemotherapeutic agent as etoposide used as positive control. Among them, compound <strong>12a</strong> bearing 3,4,5-trimethoxy substituent on the aryl moiety displayed good activity as compared with positive control against MCF-7, A549, Colo-205, and A2780 cell lines with IC<sub>50</sub> values of 1.10 ± 0.84 µM, 1.07 ± 0.067 µM, 1.20 ± 0.95 µM, and 1.34 ± 0.66 µM respectively. Compounds <strong>12a</strong> and <strong>12b</strong> primarily engage in hydrophobic interactions such as pi-pi stacked, amide-pi stacked, pi-alkyl, and alkyl interactions. Specifically, nucleotides DG13, DA12, and arg503 display pi-pi stacked and amide-pi stacked interactions.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 405-421"},"PeriodicalIF":1.8,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377777","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 one-pot green synthesis, antioxidant and antimicrobial activities of 7-(substituted phenyl)-7,11-dihydro-6H,8H-chromeno[3′,4′:5,6]pyrano[2,3-d]pyrimidine-6,8,10(9H)-trione derivatives","authors":"Omkar Reddy Vanukuri , Mohan Gundluru , Poojitha Bellala , Rama Sekhara Reddy Dachuru , Suresh Reddy Cirandur","doi":"10.1080/00397911.2025.2455521","DOIUrl":"10.1080/00397911.2025.2455521","url":null,"abstract":"<div><div>The work aims to develop a simple and efficient protocol for one-pot three-component synthesis to produce a series of poly functionalized 7-(substituted phenyl)-7,11-dihydro-6H,8H-chromeno[3′,4′:5,6]pyrano[2,3-d]pyrimidine-6,8,10(9H)-trione derivatives using Sulfonated reduced graphene oxide (rGO-SO<sub>3</sub>H) as an efficient catalyst <em>via</em> one-pot multicomponent reaction of 4-hydroxycoumarin, aromatic aldehydes and barbituric acid under microwave irradiation and solvent-free conditions in good to excellent yields. The reported protocol is metal-free, highly atom-economic, better yielding in quick reaction time, simple to operate and eco-friendly with reaction conditions comparatively milder. Use of low-cost acidic catalyst under neat conditions makes the reaction an environmentally benign protocol. Additionally, the compounds were screened for their free radical scavenging, antibacterial and antifungal activities which showed good activities when compared than that of standard drugs.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 4","pages":"Pages 325-337"},"PeriodicalIF":1.8,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143378068","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":"A practical synthesis of functionalized pyrazoles promoted by a polyoxomolybdate-based iron catalyst","authors":"Lianji Zhang , Yujuan Wu , Cuiping Wang , Wanguo Wei , Zhiqiang Zhang","doi":"10.1080/00397911.2025.2455529","DOIUrl":"10.1080/00397911.2025.2455529","url":null,"abstract":"<div><div>An efficient synthesis of pyrazole scaffolds from arylsulfonylhydrazines and diketones promoted by a molecular molybdenum oxide catalyst (NH<sub>4</sub>)<sub>3</sub>[FeMo<sub>6</sub>O<sub>18</sub>(OH)<sub>6</sub>] is described. The iron-based polyoxometalate catalyst is heterogeneous, reusable with stable recyclability. Using this method, a wide range of arylsulfonylhydrazines and diketones can undergo smoothly condensation cyclization to produce functionalized pyrazoles in high yields.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 373-380"},"PeriodicalIF":1.8,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377644","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":"Electrochemical regioselective methylthiolation of imidazo[2,1-b]thiazoles with DMSO","authors":"Meng Xiao , Liyu Yi , Wenjie Liu , Gao Cao","doi":"10.1080/00397911.2025.2453872","DOIUrl":"10.1080/00397911.2025.2453872","url":null,"abstract":"<div><div>With DMSO both as the source of -SMe unit and solvent, an efficient and green electrochemical methylthiolation reaction of imidazo[2,1-<em>b</em>]thiazoles was developed. The transformation was performed at room temperature in 8 h under external transition metal- and oxidant-free condition. Moreover, the 2,3-dihydroimidazo[2,1-<em>b</em>]thiazoles and 2-phenylbenzo[d]imidazo[2,1-<em>b</em>]thiazole also proceeded smoothly. This strategy provides C-5 methylthiolation products with broad scope in 73–91% yields.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 4","pages":"Pages 338-349"},"PeriodicalIF":1.8,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143378070","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}
Umar B. Suleiman , Mansur B. Ibrahim , Aminu Muhammad , Sani. A. Zarewa
{"title":"Synthesis of Felbinac acid and Felbinac ester via PEPPSI palladium N-heterocyclic carbene catalytic system","authors":"Umar B. Suleiman , Mansur B. Ibrahim , Aminu Muhammad , Sani. A. Zarewa","doi":"10.1080/00397911.2025.2453977","DOIUrl":"10.1080/00397911.2025.2453977","url":null,"abstract":"<div><div>Ethyl-4-biphenylacetate (Felbinac ester) and 4-biphenylacetic acid (Felbinac acid) are common active metabolites of non-steroidal anti-inflammatory drugs (NSAIDs) and are frequently used in the treatment of muscle inflammation and arthritis. The current studies synthesized Felbinacs via a Suzuki-Miyaura cross-coupling reaction mediated through PEPPSI-palladium N-heterocyclic carbene as a catalyst. The catalyst was synthesized through <em>N</em>-benzylation of benzimidazole followed by <em>N</em>-butylation of the resulting <em>N</em>-benzylbenzimidazole to yield the <em>N</em>-benzyl-<em>N</em>-butylbenzimidazolium bromide (the pre-carbene). The pre-carbene was then reacted with palladium bromide (PdBr<sub>2</sub>) in 3-methylpyridine, to produce the pre-catalyst (Pd-NHC-Py-Br<sub>2</sub>). The intermediates and the pre-catalyst were characterized using <sup>1</sup>H and <sup>13</sup>C NMR, FT-IR, and elemental analyses. The pre-catalyst was used to mediate the synthesis of 4-biphenylacetic acid (Felbinac acid) and 4-biphenylacetate (Felbinac ester) from the coupling reaction of Ethyl-4-bromophenyl acetate with phenylboronic acid. The Pd-NHC-Py-Br2 pre-catalyst demonstrated excellent air and moisture stability.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 4","pages":"Pages 315-324"},"PeriodicalIF":1.8,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143378069","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}