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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
N-heterocyclic carbene-catalyzed nucleophilic aromatic substitution reaction of polyfluoroarenes N- 异环碳烯催化的多氟烯烃亲核芳香取代反应
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-28 DOI: 10.1080/00397911.2024.2395993
Lishuai Lu , Dengyu Yin , Xiao-Xuan Li , Yandong Dou , Yanwu Zhu , Shilu Fan
{"title":"N-heterocyclic carbene-catalyzed nucleophilic aromatic substitution reaction of polyfluoroarenes","authors":"Lishuai Lu ,&nbsp;Dengyu Yin ,&nbsp;Xiao-Xuan Li ,&nbsp;Yandong Dou ,&nbsp;Yanwu Zhu ,&nbsp;Shilu Fan","doi":"10.1080/00397911.2024.2395993","DOIUrl":"10.1080/00397911.2024.2395993","url":null,"abstract":"<div><p>Fluorinated asymmetric aryl ketones represent a pivotal class of organic synthesis intermediates, which have garnered widespread application in the realms of organic chemistry, materials science, and drug discovery. Herein, we report a pioneering nucleophilic aromatic substitution (S<em>N</em>Ar) reaction involving aryl aldehydes and polyfluoroarenes, elegantly catalyzed by N-heterocyclic carbene (NHC). This innovative strategy yields bis(hetero)aryl ketone products in yields ranging from moderate to exceptional (40–83%), all achieved under gentle conditions, devoid of both transition metals and directing groups. The versatility of this method is underscored by its compatibility with a broad spectrum of substrates, particularly exhibiting remarkable resilience toward alkoxy functional groups. Notably, we have successfully transformed an array of biologically active molecules, crafting a series of their corresponding derivatives with precision.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1551-1563"},"PeriodicalIF":1.8,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172590","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
Chemo-enzymatic, regioselective synthesis of dihydropyrimidinone-fused β-amino alcohols and their anti-inflammatory and antioxidant activity evaluation 二氢嘧啶酮融合β-氨基醇的化学酶促、区域选择性合成及其抗炎和抗氧化活性评价
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-27 DOI: 10.1080/00397911.2024.2396500
Sumit Kumar , Aditi Arora , Madhulika Singh , Brajendra K. Singh , Chandrani Mukherjee , Sunil K. Singh
{"title":"Chemo-enzymatic, regioselective synthesis of dihydropyrimidinone-fused β-amino alcohols and their anti-inflammatory and antioxidant activity evaluation","authors":"Sumit Kumar ,&nbsp;Aditi Arora ,&nbsp;Madhulika Singh ,&nbsp;Brajendra K. Singh ,&nbsp;Chandrani Mukherjee ,&nbsp;Sunil K. Singh","doi":"10.1080/00397911.2024.2396500","DOIUrl":"10.1080/00397911.2024.2396500","url":null,"abstract":"<div><p>A highly regioselective and efficient method has been developed for synthesizing novel <em>β</em>-amino alcohols fused with dihydropyrimidin-2-one. This method utilizes the enzyme <em>Novozyme-435</em> to catalyze the reaction between epoxides and various aliphatic amines in acetonitrile. <em>Novozyme-435</em> outperformed other catalysts, including <em>Porcine Pancreatic Lipase</em> (PPL), <em>Pseudomonas aeruginosa lipase</em> (PAL), and <em>Candida rugosa lipase</em> (CRL). This process yielded two series of <em>β</em>-amino alcohols (compounds <strong>8a-h</strong> and <strong>9a-h</strong>), whose structures were confirmed through IR, NMR (<sup>1</sup>H,<span><span><sup>13</sup></span></span>C), and HRMS analyses. The anti-inflammatory and antioxidant properties of these compounds were evaluated, revealing mild to moderate inhibition of TNF-<em>α</em>-induced ICAM-1 expression in primary human endothelial cells, with compounds <strong>9a</strong> and <strong>9c</strong> showing approximately 60% inhibition. Antioxidant activity, assessed using the DPPH (2,2-diphenyl-1-picrylhydrazyl) method, indicated that compounds <strong>9a</strong>, <strong>9b</strong>, <strong>9c</strong>, and <strong>9 g</strong> had the superior activity than others. This study highlights the potential of these <em>β</em>-amino alcohols fused with dihydropyrimidin-2-one as anti-inflammatory and antioxidant agents.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1564-1578"},"PeriodicalIF":1.8,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172591","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
Spectroscopic elucidation, quantum chemical computations (FMO, HOMO–LUMO, MEP, NLO), and biological activity on some novel heterocyclic compounds using 3-substituted-6,8-dimethylchromones 利用 3-取代-6,8-二甲基色素对一些新型杂环化合物进行光谱阐释、量子化学计算（FMO、HOMO-LUMO、MEP、NLO）和生物活性研究
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-27 DOI: 10.1080/00397911.2024.2394833
Mai A. Mostafa , Magdy A. Ibrahim , Al-Shimaa Badran
{"title":"Spectroscopic elucidation, quantum chemical computations (FMO, HOMO–LUMO, MEP, NLO), and biological activity on some novel heterocyclic compounds using 3-substituted-6,8-dimethylchromones","authors":"Mai A. Mostafa ,&nbsp;Magdy A. Ibrahim ,&nbsp;Al-Shimaa Badran","doi":"10.1080/00397911.2024.2394833","DOIUrl":"10.1080/00397911.2024.2394833","url":null,"abstract":"<div><p>The chemical transformations of substituted chromones <strong>1a–c</strong> were examined toward some nucleophiles namely dimedone (<strong>R1</strong>), 4-hydroxycoumarin (<strong>R2</strong>) and 4-hydroxy-1-methylquinolin-2(1<em>H</em>)-one (<strong>R3</strong>). DFT computation at the B3LYP/6-311 G(d,p) level of theory was used to perform the theoretical computations for the produced compounds. HOMO and LUMO analyses were performed to determine the electronic charge distribution and reactivity of the molecules. Molecular electrostatic potential (MEP) surface analysis was utilized to predict the molecule’s reactive sites. Moreover, the studied compounds showed NLO characteristics, where they have first order hyperpolarizability greater than urea. In addition, the GIAO method was used to estimate the <sup>1</sup>H-NMR and <sup>13</sup>C-NMR chemical shifts; and the findings were compared with experimental values. Testing the generated compounds for antibacterial and anticancer activities revealed varied degrees of inhibitory effect. According to the Lipinski, Veber, and Egen rules, these compounds exhibit physicochemical properties.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1523-1550"},"PeriodicalIF":1.8,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172589","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
Substrate-controlled chemoselective assembly of coumarins and Morita–Baylis–Hillman alcohols from salicylaldehydes with acrylates 水杨醛与丙烯酸酯在底物控制下化学选择性组装香豆素和莫里塔-贝利斯-希尔曼醇
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-08-26 DOI: 10.1080/00397911.2024.2397501
Kai-Kai Wang , Yan-Li Li , Can Wang , Lei Hua , Xueji Ma , Rongxiang Chen
{"title":"Substrate-controlled chemoselective assembly of coumarins and Morita–Baylis–Hillman alcohols from salicylaldehydes with acrylates","authors":"Kai-Kai Wang ,&nbsp;Yan-Li Li ,&nbsp;Can Wang ,&nbsp;Lei Hua ,&nbsp;Xueji Ma ,&nbsp;Rongxiang Chen","doi":"10.1080/00397911.2024.2397501","DOIUrl":"10.1080/00397911.2024.2397501","url":null,"abstract":"<div><p>Substrate-controlled divergent reactions of between salicylaldehydes and acrylates have been developed. By using methyl acrylate as the substrate with salicylaldehydes, a domino reaction was established, delivering coumarins with good yield (up to 81% yields) and high chemoselectivity under mild conditions. Whereas the methyl acrylate was changed to <em>tert</em>-butyl acrylate or <em>iso</em>-propyl acrylate, the classical Morita − Baylis − Hillman adducts were produced in good yields (up to 75% yields) under near exclusivity under the otherwise identical reaction conditions, without any other competitive products. Additionally, the synthetic utility of the present methodology was further demonstrated by synthetic transformation. The structure of the typical product was unambiguously established by single crystal X-ray diffraction analysis.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 18","pages":"Pages 1579-1588"},"PeriodicalIF":1.8,"publicationDate":"2024-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142172592","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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