Phosphorus, Sulfur, and Silicon and the Related Elements最新文献

{"title":"Oxidative cyclization leading to charged sulfur-containing tricyclic heteroarenes","authors":"Luis G. Ardón-Muñoz ,&nbsp;Jeanne L. Bolliger","doi":"10.1080/10426507.2023.2173757","DOIUrl":"https://doi.org/10.1080/10426507.2023.2173757","url":null,"abstract":"<div><p>Fused heterocycles are of crucial importance to the pharmaceutical and agrochemical industry. While their neutral analogues including the fungicide tricyclazole have been investigated for various applications and can be prepared via several synthetic pathways, charged <em>N</em>-substituted benzo[4,5]thiazolo[2,3-<em>c</em>][1,2,4]triazol-1-ium salts are not as easily accessible. In this review we summarize a new method for the synthesis of novel N-arylated and N-alkylated benzo[4,5]thiazolo[2,3-<em>c</em>][1,2,4]triazol-1-ium salts from air stable precursors and present an expanded substrate scope for this reaction. The <em>N</em>-aryl substituted precursors are available through a catalytic N-arylation previously developed in our group, while <em>N</em>-alkyl substituted precursors were prepared by a nucleophilic substitution reaction. Selective deprotection of the para-methoxybenzyl protected precursor leads to the free thiol which under oxidative conditions undergoes C–H functionalization of the linked 1,2,4-triazolium salt, thereby forming the fused aromatic heterocycle. A wide range of functional groups such as alcohols, amides, and alkynes are tolerated. Mechanistic investigations indicate the involvement of a disulfide intermediate in the oxidative cyclization step.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 536-542"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863692","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Fe3O4 nanoparticles as an efficient catalyst for one-pot synthesis of novel fused phosphorus heterocycles bearing diethyl phosphonate","authors":"Tarik E. Ali ,&nbsp;Mohammed A. Assiri ,&nbsp;Mai S.A. Hussien ,&nbsp;Noha M. Hassanin","doi":"10.1080/10426507.2023.2168271","DOIUrl":"https://doi.org/10.1080/10426507.2023.2168271","url":null,"abstract":"<div><p>An efficient and practical method for the synthesis of novel fused phosphorus heterocycles incorporating diethyl phosphonate by the one-pot in the presence of Fe₃O₄ nanoparticles as a reusable catalyst was achieved. The four-component reactions of <em>ortho-</em>substituted anilines, namely 2-aminophenol, 2-aminothiophenol and 1,2-phenylenediamine with salicylaldehyde, diethyl phosphite and hexaethylphosphorus triamide in the presence of Fe₃O₄ nanoparticles as a catalyst at 80–90<!--> <!-->°C afforded the corresponding 1,3,2-benzo(oxaza/thiaza/diaza)phospholo[2,3-<em>b</em>][1,3,2]benzoxazaphosphinines <strong>1</strong>–<strong>3</strong> in good yields (80-84%). When the same reactions were repeated by substitution of salicylaldehyde with benzaldehyde, the 1,2-benzazaphospholo[2,1-<em>b</em>][1,3,2]benzo(oxaza/thiaza)phospholes <strong>4</strong> and <strong>5</strong> and 1,3,2-benzodiazaphosphole <strong>6</strong> derivatives were isolated in 78–83% yields. The structures of the synthesized compounds were established by elemental analysis and spectroscopic techniques (IR, MS and NMR).</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 5","pages":"Pages 435-441"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49872636","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"An ultra-sound assisted synthesis of α-aminophosphonates from benzyl halides via sequential Kornblum and Kabachnik-fields reaction","authors":"Rabia Amin ,&nbsp;Tabassum Ara","doi":"10.1080/10426507.2022.2157830","DOIUrl":"https://doi.org/10.1080/10426507.2022.2157830","url":null,"abstract":"<div><p>An ultrasound-assisted simple, easy and straightforward method for the synthesis of α-aminophosphonates has been developed <em>via</em> Kornblum/Kabachnik-fields reaction. The method involves <em>in situ</em> generation of an aldehyde intermediate from benzyl halides <em>via</em> oxidative dehalogenation followed by coupling with aryl amine and trialkyl phosphite in a one-pot three component manner under ultrasonic irradiations. The developed method is compatible with various functionalities and the desired products are obtained in good to excellent yield under mild conditions.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 5","pages":"Pages 417-423"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49902486","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"The effect of citric acid on the microstructure and activity of MoP phosphide for dry reforming of methane","authors":"Zhiwei Yao ,&nbsp;Xiaojie Yao ,&nbsp;Wei Ding ,&nbsp;Yan Shi","doi":"10.1080/10426507.2022.2151063","DOIUrl":"https://doi.org/10.1080/10426507.2022.2151063","url":null,"abstract":"<div><p>A series of MoP catalysts (MoP-CA<em>x</em>) were synthesized by adding citric acid (CA) to solutions of (NH₄)₆Mo₇O₂₄·4H₂O and (NH₄)₂HPO₄ with a fixed molar ratio of Mo:P:CA = 1:1: <em>x</em> (<em>x</em> = 0, 1, 4, 8) followed by drying and reduction in H₂. The addition of CA had a significant effect on the microstructure (surface area and particle dispersion) and performance of MoP for dry reforming of methane (DRM). Among these MoP-CA<em>x</em> catalysts, the MoP-CA8 was found to show the highest catalyst stability, which should be attributed to the best matching of oxidation resistance ability and methane dissociation ability of MoP.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 5","pages":"Pages 397-402"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49902489","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Novel self curable phosphorus- and spiro phosphorus-based maleimides: synthesis, characterization, cure behavior and thermal properties","authors":"Ayyappan Ranjith ,&nbsp;Arunjunai Raj Mahendran ,&nbsp;Thangamani Rajkumar","doi":"10.1080/10426507.2023.2176499","DOIUrl":"https://doi.org/10.1080/10426507.2023.2176499","url":null,"abstract":"<div><p>Novel phosphorus- and spiro phosphorus-based maleimides such as tris[4-(2,5-dioxopyrrol-1-yl)phenyl] phosphite (TDPPI), tris[4-(2,5-dioxopyrrol-1-yl)phenyl] phosphate (TDPPA), 3,9-di[4-(2,5-dioxopyrrol-1-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane (TDU), and 3,9-di[4-(2,5-dioxopyrrol-1-yl)phenoxy]-2,4,8,10-tetraoxa-3λ⁵,9λ⁵-diphosphaspiro[5.5]undecane 3,9-dioxide (TDUD) have been synthesized. The structural characterization of the synthesized maleimides was performed using elemental analysis, Fourier transform infrared (FTIR) spectroscopy, and ¹H, ¹³C and ³¹P nuclear magnetic resonance spectral data. Melting behavior and heat changes during the materials’ physical and chemical changes as a temperature function were studied using differential scanning calorimetry (DSC). Mass loss rate, residual mass and the gases evolved during thermal degradation were examined using a thermogravimetric (TG) analyzer coupled with FTIR. All four maleimides having a low enthalpy of curing and high char residue (about 50 wt%) display better thermal stability than the parent N-(4-hydroxy phenyl)maleimide (N4HPMI). This was owing to the presence of phosphorus or spiro phosphorus moiety in conjunction with the maleimide unit. The combined impact of phosphorus and maleimide units makes the materials suitable for high-performance applications.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 7","pages":"Pages 583-590"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49700485","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Expeditious mechanochemical conversion of dihydronaphthalenyl-N-phenylhydrazine-1-carbothioamides into hydrazono-thiazolidin-4-one and hydrazono-dihydrothiazole derivatives—Spectroscopic, DFT, X-ray diffraction, and antibacterial studies","authors":"Swati Goswami ,&nbsp;R.P. Chaudhary","doi":"10.1080/10426507.2023.2189252","DOIUrl":"https://doi.org/10.1080/10426507.2023.2189252","url":null,"abstract":"<div><p>This study reports a facile mechanochemical conversion of <em>N</em>-phenylthiosemicarbazone derivatives of 1-tetralone analogs into thiazolidin-4-ones, thiazolidin-5-ylidene-acetates, and dihydrothiazoles by their condensation with chloroacetic acid, DMAD, and phenacyl bromide, respectively. Triethylammonium hydrogen sulfate [Et₃NH]⁺ [HSO₄]⁻ is employed as solid catalyst for this prompt and ecological conversion through which the target products are formed within 10–30 minutes in quantitative yields. The products have been characterized on the basis of spectroscopic data. X-ray diffraction studies of thiazolidin-5-ylidene-acetate <strong>5b</strong>, supported by DFT calculations of E/Z isomers of <strong>5b</strong>, are presented. Compounds <strong>4, 5</strong>, and <strong>7</strong> are assayed for their antibacterial prospects against <em>Staphylococcus aureus</em> (Gram-positive) and <em>Escherichia coli</em> (Gram-negative) bacterial stains. Some derivatives show highly promising antibacterial activities.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 7","pages":"Pages 615-626"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49728235","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of sulfur heterocycles by C–H bond functionalization of disulfide intermediates","authors":"Luis G. Ardón-Muñoz ,&nbsp;Jeanne L. Bolliger","doi":"10.1080/10426507.2023.2171040","DOIUrl":"https://doi.org/10.1080/10426507.2023.2171040","url":null,"abstract":"<div><p>Sulfur- and nitrogen-containing heterocycles are found in many natural products but also in most biologically active molecules used in the pharmaceutical and agrochemical industry. Among these molecules are substituted benzo[4,5]thiazolo[2,3-<em>c</em>][1,2,4]triazoles which exhibit a broad range of biological activities. Tricyclazole, a fungicide used to treat rice blast, belongs to this class of compounds. In this review we summarize the development of a new synthetic strategy to prepare benzo[4,5]thiazolo[2,3-<em>c</em>][1,2,4]triazole derivatives. The target compounds are conveniently obtained in a one pot-two step procedure from air stable <em>para</em>-methoxybenzyl protected 4-(2-mercaptophenyl)triazole derivatives which upon deprotection of the thiols undergo an oxidative cyclization to the corresponding tricyclic heteroarenes. Using this procedure, it is possible to obtain a variety of tricyclic heteroarenes which contain both electron-withdrawing and electron donating substituents as well as a wide range of synthetically useful groups, thus allowing biologically relevant groups to be introduced either before or after the heterocycle formation. Mechanistic investigations suggest that the oxidative cyclization proceeds via a disulfide intermediate.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 507-512"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863686","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of nitroarenes and azoxyarenes through the selenium-mediated on water oxidation of aryl amines","authors":"Antonella Capperucci ,&nbsp;Camilla Dalia ,&nbsp;Alessio Cenni ,&nbsp;Damiano Tanini","doi":"10.1080/10426507.2023.2166044","DOIUrl":"https://doi.org/10.1080/10426507.2023.2166044","url":null,"abstract":"<div><p>Selenium-promoted oxidations enable a broad range of valuable oxidative functional group interconversions. Anilines are oxidized with hydrogen peroxide in water in the presence of selenium catalysts. The selenium catalyst determines the nature of the oxidation product; whereas nitroarenes are obtained employing diphenyl diselenide or benzeneseleninic acid, azoxyarenes are formed using selenium dioxide or sodium seleninate. The reaction mechanism relies on the reactivity of Se(IV) active oxidants, while Se(VI) species have been demonstrated not to be involved in.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 6","pages":"Pages 526-531"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49863690","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis, reactivity, antimicrobial, and anti-biofilm evaluation of fluorinated 4-amino-3-mercapto-1,2,4-triazin-5(4H)-one and their derivatives","authors":"Nawaa Ali H. Alshammari ,&nbsp;Dina A. Bakhotmah","doi":"10.1080/10426507.2022.2150856","DOIUrl":"https://doi.org/10.1080/10426507.2022.2150856","url":null,"abstract":"<div><p>New fluorinated 1,2,4-triazin-4-ones <strong>2</strong>–<strong>24</strong> have been prepared using straightforward approaches. The reaction of 4-amino-3-mercapto-6-(trifluoromethyl)-1,2,4-triazin-5(4<em>H</em>)-one (<strong>2</strong>) with aromatic aldehydes produced 4-((4-substitutedbenzylidene)amino)-3-mercapto-6-(trifluoromethyl)-1,2,4-triazin-5(4<em>H</em>)-ones (<strong>5–9</strong>), which were cyclized by thioglycolic acid to give 2-(4-subsitiutedphenyl)-3-(3-mercapto-5-oxo-6-(trifluoromethyl)-1,2,4-triazin-4(5<em>H</em>)-yl)thiazolidin-4-ones (<strong>10–14</strong>). 7-Methyl-3-(trifluoromethyl)-4<em>H</em>-[1, 3, 4]thiadiazolo[2,3-<em>c</em>][1, 2, 4]triazin-4-one (<strong>4</strong>) was synthesized by the condensation of <strong>2</strong> with acetaldehyde or by reaction with cyano compounds, followed by self-cyclization in dry benzene. Cyclization of compound <strong>2</strong> by reaction with aromatic acids yielded 7-substitutedphenyl-3-(trifluoromethyl)-4<em>H</em>-[1, 3, 4]thiadiazolo[2,3-c][1, 2, 4]triazin-4-ones (<strong>15–19</strong>). Reaction of compound <strong>2</strong> with cyanamide produced 1-(4-oxo-3-(trifluoromethyl)-4<em>H</em>-[1, 3, 4]thiadiazolo[2,3-c][1, 2, 4]triazin-7-yl)guanidine (<strong>20</strong>). Alkylation of compound <strong>2</strong> with phenacyl bromide produced 4-amino-3-((2-oxo-2-phenylethyl)thio)-6-(trifluoromethyl)-1,2,4-triazin-5(4<em>H</em>)-one (<strong>21</strong>) which upon heating in the same media furnished 7-phenyl-3-(trifluoromethyl)-4<em>H</em>,8<em>H</em>-[1, 2, 4]triazino[3,4-b][1, 3, 4]thiadiazin-4-one (<strong>22</strong>). The reaction of Schiff′s bases <strong>5</strong> or <strong>6</strong> with phenacyl bromide gave 8-benzoyl-7-(4-halophenyl)-3-(trifluoromethyl)-4<em>H</em>,8<em>H</em>-[1, 2, 4]triazino[3,4-b][1, 3, 4]thiadiazin-4-ones (<strong>23–24</strong>). All of the newly synthesized compounds were characterized by spectral measurements and elemental analysis. The biological evaluation was also described. All compounds were screened for antibacterial, antifungal, and anti-biofilm activities. The findings confirm that the fluorinated 1,2,4-triazin-4-ones appear to be promising compounds as antibacterial, antifungal, and anti-biofilm agents.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 5","pages":"Pages 385-396"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49902490","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Optimization synthesis of phosphorous-containing natural products fosmidomycin and FR900098","authors":"Xin Wu ,&nbsp;Hongrui Ping ,&nbsp;Chunlin Song ,&nbsp;Jiang Duan ,&nbsp;Aidong Zhang","doi":"10.1080/10426507.2023.2173756","DOIUrl":"https://doi.org/10.1080/10426507.2023.2173756","url":null,"abstract":"<div><p>Fosmidomycin and its acetyl analogue FR900098 are two phosphorus-containing natural products with inhibitory activity against IspC enzyme in the 2-<em>C</em>-methyl-D-erythritol 4-phosphate (MEP) pathway of isoprenoid biosynthesis in plants and most bacteria. This work presents a facile route for the chemical synthesis of fosmidomycin and FR900098 using readily available raw materials. Through optimizing reaction conditions of the key steps of Michaelis-Becker reaction and acylation, the monosodium salts of fosmidomycin and FR900098 were obtained in yields of 60% and 66%, respectively, over six steps in the route. This unified route provides an alternative to the reported methods and makes it possible to synthesize the two valuable compounds with scalability and low cost, having the potential for application in developing new antimalarial drugs and pesticides.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"198 5","pages":"Pages 446-452"},"PeriodicalIF":1.3,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49872635","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}