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Scalable synthesis of tranexamic acid under modest reaction conditions using early stage isomerization of dimethyl 1,4-cyclohexanedicarboxylate as a key step 以 1,4-环己烷二羧酸二甲酯的早期异构化为关键步骤，在适度反应条件下规模化合成氨甲环酸
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-09-14 DOI: 10.1080/00397911.2024.2399795
{"title":"Scalable synthesis of tranexamic acid under modest reaction conditions using early stage isomerization of dimethyl 1,4-cyclohexanedicarboxylate as a key step","authors":"","doi":"10.1080/00397911.2024.2399795","DOIUrl":"10.1080/00397911.2024.2399795","url":null,"abstract":"<div><p>A commercially scalable five-step synthetic process starting from cis/trans (7:3) mixture of dimethyl 1,4-cyclohexanedicarboxylate is devised for preparation of tranexamic acid with more than 99.5% purity. All impurities are controlled as per monograph. 47% overall yield over five steps has been achieved based on recovery. Epimerization of a cis-predominant isomeric mixture to trans predominant isomeric mixture under mild conditions followed by exploiting the difference in solubility to obtain trans isomer in very high purity is the key feature of the synthesis. In addition to this, use of readily available and cost efficient raw materials/reagents, recycling of cis isomer, explicit design of downstream processing enabling the retention of the trans-stereochemistry until final API are some of the highlights of this synthesis. This process also circumvents the use of hazardous chemicals and harsh reaction conditions making it greener and safer compared to the previous reports.”</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142229238","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
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
{"title":"Deoxygenation of benzylphenyl sulfones using 1,2-bis(diphenylphosphino)ethane (dppe)/NBS under metal-free conditions","authors":"","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":null,"pages":null},"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
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
{"title":"Synthesis of furo[2,3-c]carbazoles as potent α-glucosidase and α-amylase inhibitors","authors":"","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":null,"pages":null},"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
{"title":"An efficient piperazine-based tertiary poly(amic acid) heterogeneous catalyst to prepare pyrrolidinone scaffolds","authors":"","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":null,"pages":null},"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
{"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":"","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":null,"pages":null},"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
{"title":"Friedel–crafts alkylations of indoles, furans, and thiophenes with arylmethyl acetates promoted by trimethylsilyl trifluoromethanesulfonate","authors":"","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":null,"pages":null},"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
{"title":"(Diethylamino)sulfur trifluoride (DAST)-mediated oxidation of benzylic alcohols and amines to carbonyl compounds","authors":"","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":null,"pages":null},"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
{"title":"Synthesis, anti-microbial evaluation, and in silico studies of novel quinoline-isoxazole hybrids","authors":"","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":null,"pages":null},"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
{"title":"N-heterocyclic carbene-catalyzed nucleophilic aromatic substitution reaction of polyfluoroarenes","authors":"","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":null,"pages":null},"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
{"title":"Chemo-enzymatic, regioselective synthesis of dihydropyrimidinone-fused β-amino alcohols and their anti-inflammatory and antioxidant activity evaluation","authors":"","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":null,"pages":null},"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
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