{"title":"α-Bromination of xanthenediones: A mild and efficient approach using N-bromosuccinimide","authors":"R. Shashi, N. Begum","doi":"10.1080/10426507.2021.1987432","DOIUrl":"https://doi.org/10.1080/10426507.2021.1987432","url":null,"abstract":"Abstract The present work deals with a practically efficient protocol designed for the synthesis of 2,7-dibromoxanthenediones using N-bromosuccinimide (NBS) in the presence of p-toluene sulfonic acid (PTSA). A combination of NBS and PTSA in chloroform is an efficient system for selective α-bromination of xanthenediones under mild reaction conditions. The main advantage of this method is short reaction duration, mild reaction conditions, easy work up and in addition the method provides excellent yields. All the compounds synthesized were characterized by spectroscopic techniques. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"81 1","pages":"38 - 44"},"PeriodicalIF":0.0,"publicationDate":"2021-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89925292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Arzu Binici, Aytuğ Okumuş, M. Yakut, Gamze Elmas, Z. Kılıç, Dila Koyunoğlu, L. Açık, H. Simsek
{"title":"Phosphorus-nitrogen compounds. Part 56. Comparative syntheses and spectral properties of multiheterocyclic 2-cis-4-ansa and spiro-ferrocenyl (N/O)cyclotetraphosphazenes: Antituberculosis and antimicrobial activity and DNA interaction studies","authors":"Arzu Binici, Aytuğ Okumuş, M. Yakut, Gamze Elmas, Z. Kılıç, Dila Koyunoğlu, L. Açık, H. Simsek","doi":"10.1080/10426507.2021.1986502","DOIUrl":"https://doi.org/10.1080/10426507.2021.1986502","url":null,"abstract":"Abstract In the present study, two types of starting compounds; hexachloro(N/O)-cyclotetraphosphazenes containing mono-ferrocenyl-pendant arm, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa-(2,4-ansa; 2) and mono-ferrocenyl-spiro-(spiro; 3) were prepared by the reaction of N4P4Cl8 (1) with sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (L). Reactions of 2,4-ansa (2) with excess benzylamine and n-hexylamine resulted in the formation of partly substituted 2-cis-4-dichloro-ansa-cyclotetraphosphazenes (2a and 2b). In contrast, spiro (3) gave fully substituted mono-ferrocenyl-spiro-cyclotetraphosphazenes (3a and 3b) with excess benzylamine and n-hexylamine. As expected, the 2,4-ansa cyclotetraphosphazenes (2, 2a, and 2b) have two distinct stereogenic P-centers. The structures of cyclotetraphosphazenes were evaluated by elemental analysis, ESI-MS, FTIR, 1H, 13C, and 31P-NMR techniques. The antibacterial and antifungal activities against some selected bacteria and yeast strains, antituberculosis activities against Mycobacterium tuberculosis H37Rv, and DNA cleavage activities of mono-ferrocenyl-cyclotetraphosphazenes were also discussed. Compounds 2b, 3a, and 3b exhibited antifungal activity against C. albicans (MIC= 156.3 µM) higher than reference antibiotic Ketoconazole. Moreover, four compounds displayed antituberculosis activity against the M. tuberculosis H37RV. Compound 2a (20 μg/mL) is the most potent of the four compounds. Graphical abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"78 1","pages":"18 - 29"},"PeriodicalIF":0.0,"publicationDate":"2021-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84095145","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A review on C-P bonding reactions assisted by manganese(III) acetate","authors":"Emre Biçer","doi":"10.1080/10426507.2021.1945062","DOIUrl":"https://doi.org/10.1080/10426507.2021.1945062","url":null,"abstract":"Abstract This review aims to review the published articles involved with manganese(III) acetate based free radical additions to organic compounds to obtain organophosphorus compounds. As well known, manganese(III) acetate is a long-term initiator used by chemists to form a variety of compounds. Manganese(III) initiated phosphorus-centered radicals which undergo homolytic cleavage of the P-H bond. In follow-up reactions, an addition to unsaturated compounds leads to a wide range of valuable organophosphorus compounds. Based upon the phosphorus reagent, two types of P-centered radicals are formed: Phosphinoyl-radicals result from phosphites and phosphonyl-radicals result from phosphate reagents. According to research results on P-centered radicals, phosphonyl-radicals are more reactive than phosphinoyl radicals. By use of these radicals, many phosphorylated products have been obtained with relatively high yields. The phosphates obtained by radical addition can be used as intermediates to valuable products in organic chemistry, medicinal chemistry, crop science and material chemistry. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"18 1","pages":"791 - 808"},"PeriodicalIF":0.0,"publicationDate":"2021-07-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74211133","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Platinum-Pyridine Schiff base complexes immobilized onto silica gel as efficient and low cost catalyst for hydrosilylation","authors":"Yingpeng Huo, Jiwen Hu, Feng Liu, Jiapei Wu, Yikun Zhang, Ya-lin Zhang, Qianyi Wang","doi":"10.1080/10426507.2021.1871733","DOIUrl":"https://doi.org/10.1080/10426507.2021.1871733","url":null,"abstract":"Abstract A heterogeneous platinum catalyst with tridentate pyridine Schiff base ligands supported on silica gel is reported. The catalyst was fully characterized via FTIR, solid-state 13C NMR spectroscopy, X-ray photoelectron spectroscopy (XPS), N2 adsorption/desorption analysis, X-ray diffraction (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The catalyst showed potential application in mediating hydrosilylation reactions between olefins and hydrosilanes, and it can be reused for at least five cycles. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"5 1","pages":"812 - 818"},"PeriodicalIF":0.0,"publicationDate":"2021-07-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89304817","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. Esmaeili, F. Mesbah, Abbas Moradi, A. Khojastehnezhad, M. Khalili
{"title":"Straightforward and simple synthesis of novel pyranodipyrimidine derivatives via reaction of aromatic aldehydes and heterocyclic-1,3-dicarbonyl compound","authors":"A. Esmaeili, F. Mesbah, Abbas Moradi, A. Khojastehnezhad, M. Khalili","doi":"10.1080/10426507.2021.1921775","DOIUrl":"https://doi.org/10.1080/10426507.2021.1921775","url":null,"abstract":"Abstract An efficient and simple procedure has been described for the synthesis of a novel series of polycyclic compounds containing pyranodipyrimidine core via cyclocondensation reaction of 2,3-dihydro-thiazolo[3,2-a]pyrimidine-5,7-dione and aromatic aldehyde derivatives in the presence of diisopropylethylamine as an organo-base catalyst. This procedure gave the desired products in high yields. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"110 1","pages":"819 - 825"},"PeriodicalIF":0.0,"publicationDate":"2021-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79247684","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Wafa Arar, A. Khatyr, M. Knorr, Lukas Brieger, A. Krupp, C. Strohmann, M. Efrit, A. Ben Akacha
{"title":"Synthesis, crystal structures and Hirshfeld analyses of phosphonothioamidates (EtO)2P(=O)C(=S)N(H)R (R = Cy, Bz) and their coordination on CuI and HgX2 (X = Br, I)","authors":"Wafa Arar, A. Khatyr, M. Knorr, Lukas Brieger, A. Krupp, C. Strohmann, M. Efrit, A. Ben Akacha","doi":"10.1080/10426507.2021.1927032","DOIUrl":"https://doi.org/10.1080/10426507.2021.1927032","url":null,"abstract":"Abstract The phosphonothioamidates (EtO)2P(=O)C(=S)N(H)R (L1 R = Cy; L2 R = Bz) have been prepared by nucleophilic addition of K[(EtO)2P(=O)] to R–N = C=S and crystallographically analyzed. Both compounds are associated pairwise through strong intermolecular N–H···O bonding giving rise to 10-membered supramolecular macrocycles. This intermolecular bonding has also been studied by Hirshfeld analysis of L1 and L2. Complexation of L on CuI in MeCN solution affords the dinuclear rhomboid-shaped thione complexes [{Cu(μ2-I)2Cu}(η1-L)2] (1a,b). Crystallographic characterization of 1a reveals that L1 is ligated exclusively via the thione function to the trigonal Cu(I) centers, which are interconnected through a short Cu–Cu bond of 2.6207(4) Å. In the solid state, individual dimeric complexes are associated through intermolecular N–H···O bonding generating a supramolecular 1D ribbon. The dinuclear complexes [{XHg(μ2-X)2HgX}(η1-L)2] (2a X = Br, L = Cy; 2b X = Br, L = Bz; 2c X = I, L = Bz) were formed by stoichiometric addition of L to HgX2. The molecular structures of 2b and 2c have been elucidated by X-ray diffraction studies, which show that individual complexes are connected through intermolecular N–H···O bonding generating a supramolecular 1D ribbon. Treatment of L1 with two equivalents of HgBr2 produces the tetranuclear compound [Hg4Br8(κ1-L1)2] 3, whose unusual bromide-bridged architecture has been elucidated by X-ray crystallography. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"01 1","pages":"845 - 858"},"PeriodicalIF":0.0,"publicationDate":"2021-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86089936","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"NaOH-promoted one-pot aryl isothiocyanate synthesis under mild benchtop conditions","authors":"Xinyun Liu, Hang Li, X. Yin","doi":"10.1080/10426507.2021.1927031","DOIUrl":"https://doi.org/10.1080/10426507.2021.1927031","url":null,"abstract":"Abstract In this work, we have established a green synthesis of aryl isothiocyanates promoted by the low-cost and readily available NaOH from aryl amines and carbon disulfide in a one-pot procedure. The developed protocol features no extra desulfurating reagents and mild benchtop conditions, in which NaOH serves as both the base and the desulfurating reagent to decompose the dithiocarbamate intermediate. Fourteen examples of aryl amines bearing electronic neutral, rich and poor substituents, as well as benzylamine, have proved to be compatible substrates in the developed method to furnish the corresponding isothiocyanates. The reaction has been performed on a gram scale to further demonstrate its synthetic utility. Compared to the reported base-promoted synthesis of aryl isothiocyanates that requires the use of special equipment, such as the ball mill or the microwave reactor, the simplicity in operation and scalability enables this method to efficiently access a variety of aryl isothiocyanates. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"51 1","pages":"839 - 844"},"PeriodicalIF":0.0,"publicationDate":"2021-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83295455","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. Karabörk, Ban Abdullelah Muhammed, M. Tümer, Serhan Uruş
{"title":"Organosilane-functionalized graphene oxide hybrid material: Efficient adsorbent for heavy metal ions in drinking water","authors":"M. Karabörk, Ban Abdullelah Muhammed, M. Tümer, Serhan Uruş","doi":"10.1080/10426507.2021.2012676","DOIUrl":"https://doi.org/10.1080/10426507.2021.2012676","url":null,"abstract":"Abstract Organosilane-functionalized and chemically activated graphene-supported Schiff base ligand were synthesized and characterized with XRD, SEM, EDX, TEM, UV–vis, FT-IR, and TG/DTA techniques. Graphene oxide (GO) obtained with the route of Hummer’s method was reacted with 3-(trimethoxysilyl)propylamine, then, the organosilane functionalized and amine-activated-GO was reacted with 3,5-di-tert-butylsalicylaldehyde obtained the hybrid material containing azomethine group on GO surface. The material was used as an adsorbent in order to remove cobalt(II) and zinc(II) ions in drinking water and standard solutions. The adsorption capacity of the material to cobalt(II) and zinc(II) ions were investigated by using batch method. The effect of pH, contact time, temperature, and concentration on the adsorption capacity of the material was also investigated. The enrichment factors were calculated as 441 and 675 for zinc(II) and cobalt(II), respectively. The recovery performance of the material was determined in 98.65–101.75% and 98.55–104.0% range for zinc(II) and cobalt(II) ions, respectively. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"12 1","pages":"133 - 143"},"PeriodicalIF":0.0,"publicationDate":"2021-05-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78876236","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A simple glucose route to nickel and cobalt phosphide catalysts","authors":"Wanting Zhang, Wei-Wei Ding, Zhiwei Yao, Yanlung. Shi, Yuejian Sun, Xiaoxue Kang","doi":"10.1080/10426507.2021.1924171","DOIUrl":"https://doi.org/10.1080/10426507.2021.1924171","url":null,"abstract":"Abstract In this work, we have developed a simple one-step synthesis of Ni2P and CoP phosphides based on a carbonization process. The current approach uses glucose as a reductant instead of H2 and employs inert gas as feed gas. The Ni2P/C and CoP/C obtained by the glucose route showed higher CH4-CO2 reforming performance than corresponding phosphides prepared by traditional H2 reduction method, which should be attributed to the fact that the phosphides prepared by glucose route had higher surface areas and smaller particle sizes than the ones prepared by traditional method. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"49 1","pages":"826 - 831"},"PeriodicalIF":0.0,"publicationDate":"2021-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84310049","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Fouzia Bouchareb, M. Berredjem, A. Bouzina, Meriem Guerfi
{"title":"Ultrasound-promoted, rapid and green synthesis of phosphonamide derivatives under catalyst and solvent-free conditions","authors":"Fouzia Bouchareb, M. Berredjem, A. Bouzina, Meriem Guerfi","doi":"10.1080/10426507.2020.1854254","DOIUrl":"https://doi.org/10.1080/10426507.2020.1854254","url":null,"abstract":"Abstract We report a rapid, efficient, economic, environmentally benign, and easy to scale-up method for the synthesis of phosphonamide derivatives using ultrasound irradiation, under catalyst and solvent-free conditions starting from the corresponding amine and phenyl phosphonic dichloride. The reaction was achieved in excellent isolated yield in a short reaction time at room temperature. The structures of the synthesized compounds are confirmed by elemental analysis as well as by IR and 1H, 13C, 31P NMR spectroscopic data and mass spectrometry. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"36 1","pages":"422 - 430"},"PeriodicalIF":0.0,"publicationDate":"2020-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90092916","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}