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Deoxygenation of benzylphenyl sulfones using 1,2-bis(diphenylphosphino)ethane (dppe)/NBS under metal-free conditions 在无金属条件下使用 1,2-双（二苯基膦）乙烷 (dppe)/NBS 对苄基苯砜进行脱氧反应
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-14 DOI: 10.1080/00397911.2024.2401135
Asha Joshi , Sandeep Singh , Zafar Iqbal , Prachi Rai , Saroj Ranjan De
{"title":"Deoxygenation of benzylphenyl sulfones using 1,2-bis(diphenylphosphino)ethane (dppe)/NBS under metal-free conditions","authors":"Asha Joshi ,&nbsp;Sandeep Singh ,&nbsp;Zafar Iqbal ,&nbsp;Prachi Rai ,&nbsp;Saroj Ranjan De","doi":"10.1080/00397911.2024.2401135","DOIUrl":"10.1080/00397911.2024.2401135","url":null,"abstract":"<div><p>An efficient route for the chemoselective deoxygenation of benzylphenyl sulfones to the corresponding sulfides has been developed using a mixture of 1,2-bis(diphenylphosphino)ethane(dppe) and NBS as an effective promoter. This is the first development on the deoxygenation of diverse benzylphenyl sulfones under metal-free conditions. The mild reaction conditions, formation of the water soluble by-product and tolerance of a wide range of functional groups promote its broad applications in organic synthesis.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 19","pages":"Pages 1690-1697"},"PeriodicalIF":1.8,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142228868","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}
引用次数: 0
An efficient one-step synthesis of a new series of mutifunctional olefins and direct hydroxymethylation of α-substituted β-keto esters 一步法高效合成一系列新的突变官能团烯烃和直接羟甲基化α-取代的β-酮酯
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-13 DOI: 10.1080/00397911.2024.2403775
Olfa Mhasni , Julien Legros , Farhat Rezgui
{"title":"An efficient one-step synthesis of a new series of mutifunctional olefins and direct hydroxymethylation of α-substituted β-keto esters","authors":"Olfa Mhasni ,&nbsp;Julien Legros ,&nbsp;Farhat Rezgui","doi":"10.1080/00397911.2024.2403775","DOIUrl":"10.1080/00397911.2024.2403775","url":null,"abstract":"<div><div>An efficient one-step procedure for the synthesis of a new series of multifunctional olefins by condensation of α-substituted β-diketones as well as β-phosphonoesters and benzoylated β-ketoesters with formaldehyde, using potassium carbonate in refluxing THF, followed by a deacylation reaction, is herein described. In contrast, the α-substituted β-keto esters, bearing an acyl moiety, only undergo a hydroxymethylation reaction, with no metal catalysts/activating agents, as is usually required for the process, affording the corresponding α-hydroxymethyl β-keto esters in high yields.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 20","pages":"Pages 1748-1759"},"PeriodicalIF":1.8,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142251672","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}
引用次数: 0
An efficient, green and solvent-free three-component synthesis of 2,4,6-triarylpyridines utilizing ZSM-5 as a heterogeneous catalyst 利用 ZSM-5 作为异相催化剂高效、绿色、无溶剂地合成 2,4,6-三芳基吡啶的三组分方法
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-12 DOI: 10.1080/00397911.2024.2403779
Navnath Hatvate , Juhi Gupta
{"title":"An efficient, green and solvent-free three-component synthesis of 2,4,6-triarylpyridines utilizing ZSM-5 as a heterogeneous catalyst","authors":"Navnath Hatvate ,&nbsp;Juhi Gupta","doi":"10.1080/00397911.2024.2403779","DOIUrl":"10.1080/00397911.2024.2403779","url":null,"abstract":"<div><div>ZSM-5, an efficient and reusable heterogeneous catalyst, is employed for the one-pot, three-component synthesis of 2,4,6-triarylpyridines from substituted benzaldehydes, acetophenones and ammonium acetate using a simple, efficient, and green method. Both electron-releasing and withdrawing aldehydes and ketones went smoothly into substituted 2,4,6-triarylpyridines. Notably, the present reaction was carried out in the solvent-fee condition. The key merits of the present protocol are the milder reaction condition, easy workup protocol, high yield of desired pyridines and recyclability and reusability of the catalyst. The developed protocol offers a broad scope of substrate applicability and good sustainability.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 20","pages":"Pages 1760-1770"},"PeriodicalIF":1.8,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142427825","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}
引用次数: 0
An environment-friendly phosphotungstic acid catalyzed cross-dehydrogenative coupling reaction to synthesize 9-substituted-9H-xanthenes with photoelectrochemical performance 以环境友好型磷钨酸催化交叉脱氢偶联反应合成具有光电化学性能的 9-取代-9H-氧杂蒽
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-12 DOI: 10.1080/00397911.2024.2402833
Lingyu Zhao , Yongjun Zhang , Zhirong Zhao , Kun Bi , Jiayang Zhang , Guodong Shen
{"title":"An environment-friendly phosphotungstic acid catalyzed cross-dehydrogenative coupling reaction to synthesize 9-substituted-9H-xanthenes with photoelectrochemical performance","authors":"Lingyu Zhao ,&nbsp;Yongjun Zhang ,&nbsp;Zhirong Zhao ,&nbsp;Kun Bi ,&nbsp;Jiayang Zhang ,&nbsp;Guodong Shen","doi":"10.1080/00397911.2024.2402833","DOIUrl":"10.1080/00397911.2024.2402833","url":null,"abstract":"<div><div>An environment-friendly phosphotungstic acid catalyzed cross-dehydrogenative coupling reaction for the synthesis of 9-substituted-9H-xanthenes under oxygen and solvent-free conditions have been developed. The economic and practical reaction exhibited good substrate applicability tolerance, various 9-substituted-9H-xanthenes were synthesized in moderate to excellent yields by tuning the ratio of xanthenes and ketones (22 examples, up to 99% yield). By testing the photoelectrochemical performance, some of the xanthene derivatives (<strong>10c</strong>, <strong>12c</strong>, <strong>13c</strong> and <strong>2d</strong>) showed stable photocurrent value, especially <strong>2d</strong> had better cathode photocurrent value and application potential.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 20","pages":"Pages 1725-1735"},"PeriodicalIF":1.8,"publicationDate":"2024-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142426889","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}
引用次数: 0
Synthesis of furo[2,3-c]carbazoles as potent α-glucosidase and α-amylase inhibitors 合成呋喃并[2,3-c]咔唑类强效 α-葡萄糖苷酶和 α-淀粉酶抑制剂
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-10 DOI: 10.1080/00397911.2024.2401628
Tugçe N. Uslu Uçar , Murat Bingul , Hasan Sahin , Hakan Kandemir , Ibrahim F. Sengul
{"title":"Synthesis of furo[2,3-c]carbazoles as potent α-glucosidase and α-amylase inhibitors","authors":"Tugçe N. Uslu Uçar ,&nbsp;Murat Bingul ,&nbsp;Hasan Sahin ,&nbsp;Hakan Kandemir ,&nbsp;Ibrahim F. Sengul","doi":"10.1080/00397911.2024.2401628","DOIUrl":"10.1080/00397911.2024.2401628","url":null,"abstract":"<div><p>The carbazole-3-carbaldehyde <strong>2</strong>, produced by <em>N</em>-ethyl carbazole <em>via</em> Vilsmeier-Haack reaction, was subjected to Dakin type oxidation with H<sub>2</sub>O<sub>2</sub> and H<sub>2</sub>SO<sub>4</sub> in methanol to produce the carbazole-3-ol <strong>3</strong>. The reaction of <strong>3</strong> with a range of commercially available α-haloketones <strong>4a–f</strong> in the presence of Al<sub>2</sub>O<sub>3</sub> as catalyst in xylene led to their regio-selective cyclization to afford the furo[2,3-c]carbazoles <strong>5a–f</strong>. Identification of the furo[2,3-c]carbazoles <strong>5a–f</strong> were performed through <sup>1</sup>H NMR,<sup>13</sup>C NMR, FT-IR and high resolution mass spectrometry. Single crystal X-ray diffraction analysis was employed to further confirm the structures of the some of the targeted compounds. <em>In vitro</em> antidiabetic activities of the newly synthesized furocarbazoles <strong>5a–e</strong> were investigated utilizing α-glucosidase and α-amylase enzymes. The biological evaluation revealed the obvious efficiencies of the targeted molecules toward the α-glucosidase enzyme inhibition with the potent IC<sub>50</sub> values compared to the standard acarbose. In the case of α-glucosidase inhibition, the furo[2,3-c]carbazoles chloro substituted <strong>5c</strong> and nitro substituted <strong>5f</strong> were found to be more potent than acarbose with the values of 215.0 and 162.70 μM, respectively. On the other hand, the compound <strong>5f</strong> was found to be only promising candidate for α-amylase enzyme but not as effective as the standard acarbose.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 19","pages":"Pages 1698-1706"},"PeriodicalIF":1.8,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142229239","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}
引用次数: 0
An efficient piperazine-based tertiary poly(amic acid) heterogeneous catalyst to prepare pyrrolidinone scaffolds 制备吡咯烷酮支架的高效哌嗪基三级聚（胺酸）异相催化剂
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-05 DOI: 10.1080/00397911.2024.2400561
Rita Sharmila Dewi , Lia Zaharani , Mohd Rafie Johan , Nader Ghaffari Khaligh
{"title":"An efficient piperazine-based tertiary poly(amic acid) heterogeneous catalyst to prepare pyrrolidinone scaffolds","authors":"Rita Sharmila Dewi ,&nbsp;Lia Zaharani ,&nbsp;Mohd Rafie Johan ,&nbsp;Nader Ghaffari Khaligh","doi":"10.1080/00397911.2024.2400561","DOIUrl":"10.1080/00397911.2024.2400561","url":null,"abstract":"<div><p>Given the abundance of functional groups, meso- and macro-pores, and a high surface area, the piperazine-based poly(amic acid) was employed as a heterogeneous catalyst in the multicomponent reaction to prepare pyrrolidinone scaffolds in a green solvent, acting as a medium for mass transfer and crystallization solvent. The important parameters of the reaction were investigated to find the optimal reaction conditions. A conversion of 100% was obtained at reflux conditions within 30–100 min using a catalytic amount of 200 mg of piperazine-based poly(amic acid) per 2 mmol of reactants (100 mg of cat./1 mmol of reactant). The piperazine-based poly(amic acid) exhibited high recyclability and the recovered catalyst could be used in successive runs without worthy loss in its activity. This work revealed the catalytic activity of the piperazine-based poly(amic acid) as a promising functional polymeric heterogeneous catalyst for organic synthesis.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 19","pages":"Pages 1679-1689"},"PeriodicalIF":1.8,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142216109","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}
引用次数: 0
Design, synthesis and structural studies of oxathiepine, benzo[b][1, 4]thiazine and quinolin-4-ol derivative based on 3-bromo-4-hydroxy-7-methoxyquinolin-2-one 基于 3-溴-4-羟基-7-甲氧基喹啉-2-酮的噁硫平、苯并[b][1, 4]噻嗪和喹啉-4-醇衍生物的设计、合成和结构研究
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-03 DOI: 10.1080/00397911.2024.2397814
Alaa E. Hassanien
{"title":"Design, synthesis and structural studies of oxathiepine, benzo[b][1, 4]thiazine and quinolin-4-ol derivative based on 3-bromo-4-hydroxy-7-methoxyquinolin-2-one","authors":"Alaa E. Hassanien","doi":"10.1080/00397911.2024.2397814","DOIUrl":"10.1080/00397911.2024.2397814","url":null,"abstract":"<div><p>4-Hydroxy-7-methoxyquinolin-2-one (<strong>1</strong>) and its derivative 3-bromo-4-hydroxy-7-methoxyquinolin-2-one (<strong>2</strong>) serve as valuable intermediates for the synthesis of advanced hetero-compounds. The reactivity of compound (<strong>2</strong>) has been verified through multiple substitution reactions. Their reactions with 2-mercaptoacetic acid, 3-mercaptopropanoic acid, or 2-aminobenzoic acid resulted in the corresponding hetero-compounds with high yields. The synthesized compounds underwent thorough examination via elemental and spectral analyses. Additionally, DFT calculations confirmed their structures in accordance with spectral investigations. Furthermore, the study delved into the global chemical reactivity parameters.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 19","pages":"Pages 1652-1664"},"PeriodicalIF":1.8,"publicationDate":"2024-09-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142229237","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}
引用次数: 0
Friedel–crafts alkylations of indoles, furans, and thiophenes with arylmethyl acetates promoted by trimethylsilyl trifluoromethanesulfonate 在三氟甲磺酸三甲基硅酯的促进下，吲哚、呋喃和噻吩与芳基甲基乙酸酯的 Friedel-Crafts 烷基化反应
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-02 DOI: 10.1080/00397911.2024.2397717
Helen L. Xia , Eric Zhou , Bianca Bicalho , C. Wade Downey
{"title":"Friedel–crafts alkylations of indoles, furans, and thiophenes with arylmethyl acetates promoted by trimethylsilyl trifluoromethanesulfonate","authors":"Helen L. Xia ,&nbsp;Eric Zhou ,&nbsp;Bianca Bicalho ,&nbsp;C. Wade Downey","doi":"10.1080/00397911.2024.2397717","DOIUrl":"10.1080/00397911.2024.2397717","url":null,"abstract":"<div><p>Various indoles undergo Friedel–Crafts alkylation at the 3-position when treated with secondary arylmethyl acetates in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine. Tertiary benzylic alcohols are also effective alkylating agents, undergoing TMSOTf-promoted activation to yield alkylated indoles that feature quaternary centers. A related study shows that benzofuran reacts under similar conditions to yield 2-alkylated benzofurans when treated with similar alkylating agents, and the reaction has been extended to include other representative heteroarenes. Yields for these Friedel–Crafts alkylation products range from 43%–99% over a wide range of substrate combinations.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1589-1602"},"PeriodicalIF":1.8,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172593","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}
引用次数: 0
(Diethylamino)sulfur trifluoride (DAST)-mediated oxidation of benzylic alcohols and amines to carbonyl compounds (三氟化硫（DAST）介导的苄醇和胺氧化成羰基化合物的过程
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-29 DOI: 10.1080/00397911.2024.2397499
Dylan Smeyne , Steven Boyles , Ricardo Belloso , Katherine Verboom , Bryce White , Abid Shaikh
{"title":"(Diethylamino)sulfur trifluoride (DAST)-mediated oxidation of benzylic alcohols and amines to carbonyl compounds","authors":"Dylan Smeyne ,&nbsp;Steven Boyles ,&nbsp;Ricardo Belloso ,&nbsp;Katherine Verboom ,&nbsp;Bryce White ,&nbsp;Abid Shaikh","doi":"10.1080/00397911.2024.2397499","DOIUrl":"10.1080/00397911.2024.2397499","url":null,"abstract":"<div><p>We report an efficient protocol for oxidation of primary/secondary benzyl alcohols and benzylamines to produce corresponding aldehydes or ketones. Our unified method involves the use of commercially available (diethylamino)sulfur trifluoride (DAST) as a reagent combined with DMSO as solvent and oxidant. The reaction provided corresponding carbonyl compounds in good to excellent yields with high purity and in short reaction times.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1620-1628"},"PeriodicalIF":1.8,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172955","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}
引用次数: 0
Synthesis, anti-microbial evaluation, and in silico studies of novel quinoline-isoxazole hybrids 新型喹啉-异噁唑杂交化合物的合成、抗微生物评价和硅学研究
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-29 DOI: 10.1080/00397911.2024.2397813
Deep P. Mandir , Shivani D. Mandir , Jignesh H. Kamdar , Satishkumar D. Tala
{"title":"Synthesis, anti-microbial evaluation, and in silico studies of novel quinoline-isoxazole hybrids","authors":"Deep P. Mandir ,&nbsp;Shivani D. Mandir ,&nbsp;Jignesh H. Kamdar ,&nbsp;Satishkumar D. Tala","doi":"10.1080/00397911.2024.2397813","DOIUrl":"10.1080/00397911.2024.2397813","url":null,"abstract":"<div><p>A series of novel quinoline-isoxazole hybrids <strong>6a–o</strong> has been synthesized via multistep synthetic approach involving hetero Diels-alder reaction strategy. The target compounds were obtained in good yield, using low-cost readily available starting materials using simple reaction conditions. The newly synthesized compounds were confirmed using <sup>1</sup>H NMR,<sup>13</sup>C NMR, and Mass spectroscopic analysis techniques. Further, compounds <strong>6a–o</strong> were subjected to <em>in vitro</em> antimicrobial screening against various bacterial and fungal strains, such as <em>Bacillus subtilis</em>, <em>Staphylococcus aureus</em>, <em>Escherichia coli</em>, <em>Salmonella typhi</em>, <em>Aspergillus niger</em>, and <em>Candida albicans</em>. Among these, compounds <strong>6i</strong>, <strong>6j</strong>, and <strong>6 l</strong> were found most active having equally potent compared to standard drug Ampicillin and Gentamycin. Moreover, <em>in silico</em> studies of <strong>6a–o</strong> with <em>E. coli</em> DNA gyrase through molecular docking and MD simulations showed excellent binding properties of these derivatives with protein site.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1603-1619"},"PeriodicalIF":1.8,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172878","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}
引用次数: 0
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