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Reduction of styrene compounds by hydrogen iodide 碘化氢还原苯乙烯化合物
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-17 DOI: 10.1080/00397911.2024.2375547
{"title":"Reduction of styrene compounds by hydrogen iodide","authors":"","doi":"10.1080/00397911.2024.2375547","DOIUrl":"10.1080/00397911.2024.2375547","url":null,"abstract":"<div><p>Reduction of styrene compounds was achieved by the simple method of adding more than 2.5 equivalents of an aqueous HI solution in chlorobenzene under refluxing conditions for 8 h to give the product in medium to excellent yields. There was no need to add further additional reagent and catalyst. HI was a specific reagent for this reduction reaction. Increment of the amount of HI was efficient to increase the yield rather than to elongate the reaction time. This reaction could be applied to compounds bearing halogen and sulfur atoms, which would act as reductive site and poisoning of the transition-metal catalyst, respectively. The yield was decreased in the case of the compounds bearing small substituent such as propyl and butyl groups on olefin. This reaction proceeded via the iodinated intermediate followed by the reduction of C-I bond. The reduction mechanism would contain the radical cleavage of the C-I bond.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 14","pages":"Pages 1159-1167"},"PeriodicalIF":1.8,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141584943","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 polysubstituted pyrazoles and their biological applications 多取代吡唑的合成及其生物应用
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-17 DOI: 10.1080/00397911.2024.2377283
Appalanaidu Satipidakala , Ramakrishna Rao Bhonsle , Ramana Tamminana
{"title":"Synthesis of polysubstituted pyrazoles and their biological applications","authors":"Appalanaidu Satipidakala ,&nbsp;Ramakrishna Rao Bhonsle ,&nbsp;Ramana Tamminana","doi":"10.1080/00397911.2024.2377283","DOIUrl":"10.1080/00397911.2024.2377283","url":null,"abstract":"<div><p>Novel library of pyrazole derivatives (<strong>6a–k)</strong> from substituted 4-dioxaborolanyl-1<em>H</em>-pyrazole and halo benzaldehyde through simultaneous Suzuki reaction, nucleophilic addition, and hydrolysis under moderate reaction conditions. The desired compounds <strong>6a–k</strong> have been formed in good to high yield. All the compound structures were characterized by analytical and spectral (<sup>1</sup>H NMR,<sup>13</sup>C NMR and MS) studies. Furthermore, the evaluation of biological activity of synthesized molecules.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 14","pages":"Pages 1177-1185"},"PeriodicalIF":1.8,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141613377","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
One-step construction of indolo[2,1-a]isoquinolines using solid calcium carbide as an alternative to gaseous acetylene 用固体电石替代气态乙炔，一步法制备吲哚并[2,1-a]异喹啉类化合物
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-17 DOI: 10.1080/00397911.2024.2379448
Xinjie You , Botao Wang , Fei Wen , Zheng Li
{"title":"One-step construction of indolo[2,1-a]isoquinolines using solid calcium carbide as an alternative to gaseous acetylene","authors":"Xinjie You ,&nbsp;Botao Wang ,&nbsp;Fei Wen ,&nbsp;Zheng Li","doi":"10.1080/00397911.2024.2379448","DOIUrl":"10.1080/00397911.2024.2379448","url":null,"abstract":"<div><p>An efficient method for the synthesis of indolo[2,1-<em>a</em>]isoquinolines using calcium carbide as an alkyne source, 2-(2-bromophenyl)-1<em>H</em>-indoles as starting materials, and copper as a catalyst is described. The target products are synthesized <em>via</em> Sonogashira cross-coupling/nucleophilic addition tandem reactions. The advantages of this protocol include the use of inexpensive and easy-to-handle solid alkyne source instead of flammable and explosive gaseous acetylene, cheap and readily available raw materials, wide range of substrates, and simple reaction procedure. The method can also be extended to gram scale. In addition, the desired product can also be obtained by one-pot three-component reaction of phenylhydrazine hydrochlorides, <em>o</em>-bromoacetophenones and calcium carbide.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 14","pages":"Pages 1209-1219"},"PeriodicalIF":1.8,"publicationDate":"2024-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141742560","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
Quinoline-thiazole-1,2,3 triazole hybrids: Synthesis, antimalarial, antimicrobial activity and molecular docking studies 喹啉-噻唑-1,2,3 三唑杂化物：合成、抗疟、抗菌活性和分子对接研究
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-02 DOI: 10.1080/00397911.2024.2364848
Archna Yadav , C. P. Kaushik , Mahavir Parshad , Priyanka Yadav , Jyoti Yadav , Jyoti Sangwan
{"title":"Quinoline-thiazole-1,2,3 triazole hybrids: Synthesis, antimalarial, antimicrobial activity and molecular docking studies","authors":"Archna Yadav ,&nbsp;C. P. Kaushik ,&nbsp;Mahavir Parshad ,&nbsp;Priyanka Yadav ,&nbsp;Jyoti Yadav ,&nbsp;Jyoti Sangwan","doi":"10.1080/00397911.2024.2364848","DOIUrl":"10.1080/00397911.2024.2364848","url":null,"abstract":"<div><p>A series of quinoline-thiazole appended 1,4-disubstituted 1,2,3-triazole were synthesized by performing Cu(I) catalyzed 1,3-dipolar cycloaddition reaction (“Click” reaction) and fully characterized by various spectral techniques like FTIR, NMR and HRMS. These compounds were evaluated for <em>in vitro</em> antimalarial activity against <em>plasmodium falciparum</em>. All the compounds (<strong>7a–7y</strong>) exhibited moderate to good activity in comparison to standard drug Quinine. Compound <strong>7r</strong> (IC<sub>50</sub> 0.19 µg/mL) displayed appreciable activity comparable to Quinine (IC<sub>50</sub> 0.268 µg/mL). Further antimicrobial screening of the synthesized substituted triazoles were also carried out against two gram (+) bacteria (<em>Staphylococcus aureus</em>, <em>Bacillus subtilis</em>), two gram (–) bacteria <em>(Escherichia coli</em>, <em>Klebsiella pneumonia)</em> and two fungi (<em>Candida albicans</em>, <em>Aspergillus niger</em>). Results revealed that compound <strong>7r</strong> reflected promising antimicrobial activity among the synthesized library of molecules. Molecular docking studies of broadly active antimalarial disubstituted triazoles <strong>7m</strong> and <strong>7r</strong> were explored in the active site of enzyme dihydroorotate dehydrogenase (DHODH) to have the probable mode of action.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1068-1085"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141529015","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
Novel synthesis of a new class of substituted S-glycosylisothiourea derivatives and their conversion to 5-amino-1,2,4-triazoles 一类新的取代 S-糖基异硫脲衍生物的新合成及其向 5-氨基-1,2,4-三唑的转化
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-02 DOI: 10.1080/00397911.2024.2364029
Mamdouh A. Abu-Zaied , Galal A. Nawwar , Galal H. Elgemeie
{"title":"Novel synthesis of a new class of substituted S-glycosylisothiourea derivatives and their conversion to 5-amino-1,2,4-triazoles","authors":"Mamdouh A. Abu-Zaied ,&nbsp;Galal A. Nawwar ,&nbsp;Galal H. Elgemeie","doi":"10.1080/00397911.2024.2364029","DOIUrl":"https://doi.org/10.1080/00397911.2024.2364029","url":null,"abstract":"<div><p>The one-pot reaction of potassium cyanocarbamimidothiolates with acetylated bromo sugars produced a novel class of substituted glycosylisothiourea derivatives <strong>5a–h</strong> that demonstrated their Z-configuration. Some of the later compounds <strong>5a–d</strong> were treated with NH<sub>3</sub> in methanol at 25 °C, to afford the unprotected thioglycoside functionalized compounds <strong>6a–c</strong> with excellent yields. To characterize the structure of the newly synthesized compounds, various techniques, such as elemental analysis and spectral data (<sup>13</sup>C NMR, IR, and <sup>1</sup>H NMR) were employed. Furthermore, the substituted <em>S-</em>glycosylisothioureas <strong>5</strong> and <strong>6</strong> were subjected to a reaction with hydrazine hydrate, resulting in the formation of corresponding 5-amino-1,2,4-triazole derivatives <strong>7a–d.</strong> The antibacterial properties of all newly synthesized compounds were thoroughly assessed and evaluated. Among these compounds, the most potent antimicrobial agents were found to be compounds <strong>5a</strong>, <strong>5g</strong>, <strong>6a</strong>, <strong>6b</strong>, and <strong>6c</strong>.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1115-1127"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141543426","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 β-phosphonomalonates using a recyclable choline hydroxide catalyst 使用可回收氢氧化胆碱催化剂合成 β-磷酰丙二酸盐
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-02 DOI: 10.1080/00397911.2024.2368771
Reddi Mohan Naidu Kalla , M. Varalakshmi , C. Raju , Jaewoong Lee
{"title":"Synthesis of β-phosphonomalonates using a recyclable choline hydroxide catalyst","authors":"Reddi Mohan Naidu Kalla ,&nbsp;M. Varalakshmi ,&nbsp;C. Raju ,&nbsp;Jaewoong Lee","doi":"10.1080/00397911.2024.2368771","DOIUrl":"10.1080/00397911.2024.2368771","url":null,"abstract":"<div><p>Choline hydroxide (ChOH) is an effective ionic liquid (IL) that enables the straightforward construction of β-phosphonomalonates in basic medium. A variety of compounds, including aromatic/heterocyclic and aliphatic aldehydes (<strong>1a–p</strong>) were reacted with dicyanomethane (<strong>2</strong>) and diethyl phosphonate (<strong>3</strong>) to produce the targeted products in good yields (<strong>4a–p</strong>). The constructed compounds as well as the IL were characterized using spectral <sup>1</sup>H, <sup>13</sup>C, and <sup>31</sup>P NMR.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1096-1103"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141503586","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
Regiospecific synthesis of N,N’-disubstituted-2-imino-hydantoins derived from cyanamides 由氰酰胺衍生的 N,N'-二取代-2-亚氨基海因的区域特异性合成
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-02 DOI: 10.1080/00397911.2024.2368765
Mai M. Khalaf , Hany M. Abd El-Lateef , Amr H. Moustafa , Mohamed F. Awad , M. Gouda , Doaa H. Ahmed
{"title":"Regiospecific synthesis of N,N’-disubstituted-2-imino-hydantoins derived from cyanamides","authors":"Mai M. Khalaf ,&nbsp;Hany M. Abd El-Lateef ,&nbsp;Amr H. Moustafa ,&nbsp;Mohamed F. Awad ,&nbsp;M. Gouda ,&nbsp;Doaa H. Ahmed","doi":"10.1080/00397911.2024.2368765","DOIUrl":"10.1080/00397911.2024.2368765","url":null,"abstract":"<div><p>The present work developed a new simple method and convenient procedure to synthesize a novel series of 1-(4,6-dimethylpyrimidin-2-yl)-2-imino-3-arylimidazolidin-4-ones <strong>3</strong>. The sodium salt of <em>N</em>-(4,6-dimethylpyrimidin-2-yl)cyanamide (<strong>1</strong>) was selected to use as the starting material to undergo intramolecular cyclization reaction with 2-chloro-<em>N</em>-arylacetamides in boiling acetone for about 12–18 hours. According to this new synthetic route, eleven imino-hydantoins were readily separated in moderate to excellent yields as single products after cooling the reaction without any purification technique. Also, on the basis of the experimental results and analysis data (IR, NMR, elemental analyses, and GC-MS spectra), the reaction is regiospecific as well as a plausible mechanism to form the target products <strong>3</strong> instead of di-imino-oxazolidines <strong>4</strong> and/or 2-imino-2,3-dihydro-oxazoles <strong>5</strong> is proposed.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1086-1095"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141503587","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
Catalyst- and chromatography-free multi-component domino synthesis of 5-alkyl barbituric acids at room temperature 室温下无催化剂和色谱法多组分合成 5-烷基巴比妥酸
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-02 DOI: 10.1080/00397911.2024.2363376
Biswajita Baruah , Monoj Sarma , Gaurav K. Rastogi , Mohit L. Deb
{"title":"Catalyst- and chromatography-free multi-component domino synthesis of 5-alkyl barbituric acids at room temperature","authors":"Biswajita Baruah ,&nbsp;Monoj Sarma ,&nbsp;Gaurav K. Rastogi ,&nbsp;Mohit L. Deb","doi":"10.1080/00397911.2024.2363376","DOIUrl":"10.1080/00397911.2024.2363376","url":null,"abstract":"<div><p>5-Alkylated barbituric acids are an important class of compounds that constitute the basic moiety of several clinically used hypnotic drugs. Here we report a catalyst-free domino Knoevenagel-Michael addition involving barbituric acid, aldehyde, and <em>N,N</em>-disubstituted aniline in solvent acetonitrile to synthesize 5-alkylated barbituric acid derivatives (72–94% yield) without using any chromatographic separation techniques. The C-4 position of aniline acts as the Michael donor. All the reactions are successfully performed without catalysts, providing an environment-friendly and economical route for the synthesis. Moreover, catalyst-free reactions are less sensitive to air and moisture unlike many metal catalysts, with easy separation of products, and simple operating procedures as there is no need for catalyst weighing, recovery, and removal. A plausible mechanism is also proposed based on control experiments.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1051-1059"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141526957","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
Tetrabutylammonium hydroxide (TBAH) ionic liquid for the sustainable and efficient production of α-hydroxyphosphonates 四丁基氢氧化铵（TBAH）离子液体用于可持续高效生产α-羟基膦酸盐
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-02 DOI: 10.1080/00397911.2024.2368776
Reddi Mohan Naidu Kalla , Jaewoong Lee
{"title":"Tetrabutylammonium hydroxide (TBAH) ionic liquid for the sustainable and efficient production of α-hydroxyphosphonates","authors":"Reddi Mohan Naidu Kalla ,&nbsp;Jaewoong Lee","doi":"10.1080/00397911.2024.2368776","DOIUrl":"https://doi.org/10.1080/00397911.2024.2368776","url":null,"abstract":"<div><p>Ionic liquids were known as eco-solvents/catalysts, encourages the clean hydrophosphonylation of aldehydes to produce structurally various α-hydroxyphosphonates in a well-organized and ecologically friendly manner. This study used tetrabutylammonium hydroxide (TBAH) used to addition phosphite nucleophiles to aldehydes under neat condition, resulting in different α-hydroxyphosphonates that are essential components of the modern chemical industry. The current method produces targeted compounds from a wide range of aromatic, and heteroaromatic aldehydes with various substitution. The current protocol has high impact because it allows for the formation of desired products in good yields. This catalyst is applicable for gram scale synthesis of the targeted product and without any additional energy (Microwave, ultrasonication, ball milling and thermal heating). Some reported methods used various external sources (mechano-chemical) for the synthesis of α-hydroxyphosphonates.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1104-1114"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141543427","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
Rearrangement reactions: Important tool for the synthesis of piperazines 重排反应：合成哌嗪的重要工具
IF 1.8 3区 化学
Synthetic Communications Pub Date : 2024-07-02 DOI: 10.1080/00397911.2024.2355471
Upasana Sharma , Rajnish Kumar , Avijit Mazumder , Saahuddin Salahuddin , Neelima Kukreti , Pankaj Kumar Tyagi , Navneet Khurana
{"title":"Rearrangement reactions: Important tool for the synthesis of piperazines","authors":"Upasana Sharma ,&nbsp;Rajnish Kumar ,&nbsp;Avijit Mazumder ,&nbsp;Saahuddin Salahuddin ,&nbsp;Neelima Kukreti ,&nbsp;Pankaj Kumar Tyagi ,&nbsp;Navneet Khurana","doi":"10.1080/00397911.2024.2355471","DOIUrl":"10.1080/00397911.2024.2355471","url":null,"abstract":"<div><p>A six-membered heterocyclic compound known as piperazine has two nitrogen atoms within a ring. Numerous studies have shown that piperazine has the potential to be a useful pharmacophore in many harmful pharmacological conditions, such as microbiocidal, anti-inflammatory, anticancer, antioxidant, etc. In this present review, we highlighted the synthetic protocols for piperazine and its analogs and the synthetic protocol for piperazine via rearrangement reactions that have been adopted in recent years. The study also involved a listing of several patents (granted), which comprised important work on piperazine and its derivatives. Among all the methods, the most commonly adopted synthetic methods included the synthesis of piperazine analogs by diaza-cope, hydrolytic, Mumm, Ugi-smiles, [2 + 3] Stevens, Aza-witting, Curtius, Schmidt rearrangement reactions, etc. These synthetic protocols have also been compared based on different reaction conditions, feasibility, and economy to help the researchers in designing their work.</p></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"54 13","pages":"Pages 1031-1050"},"PeriodicalIF":1.8,"publicationDate":"2024-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141107639","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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