Pub Date : 2021-10-27DOI: 10.1080/10426507.2021.1990923
Can Zhang, Xiaojie Li, Ruwei Shen
Abstract The Cs2CO3-promoted P-N coupling reaction of H-phosphoryl compounds and N-tosylhydrazones is reported. Formally, this transformation represents an interesting example of exchanging the sulfur and phosphorus functionalities to convert N-tosylhydrazones to N-phosphorylhydrazones. The reaction may take place via the nucleophilic interception of the in-situ generated diazo intermediates by H-phosphoryl compounds at the terminal nitrogen atom. GRAPHICAL ABSTRACT
{"title":"Cs2CO3-promoted P-N coupling reaction of H-phosphoryl compounds with N-tosylhydrazones to afford N-phosphorylhydrazones via diazo intermediates","authors":"Can Zhang, Xiaojie Li, Ruwei Shen","doi":"10.1080/10426507.2021.1990923","DOIUrl":"https://doi.org/10.1080/10426507.2021.1990923","url":null,"abstract":"Abstract The Cs2CO3-promoted P-N coupling reaction of H-phosphoryl compounds and N-tosylhydrazones is reported. Formally, this transformation represents an interesting example of exchanging the sulfur and phosphorus functionalities to convert N-tosylhydrazones to N-phosphorylhydrazones. The reaction may take place via the nucleophilic interception of the in-situ generated diazo intermediates by H-phosphoryl compounds at the terminal nitrogen atom. GRAPHICAL ABSTRACT","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"51 2","pages":"1 - 6"},"PeriodicalIF":0.0,"publicationDate":"2021-10-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91435057","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}
Pub Date : 2021-10-20DOI: 10.1080/10426507.2021.1991344
Hadi Sedighian, Kaveh Imani, A. Bazgir
Abstract A novel and efficient three-component reaction of substituted benzoyl chlorides, potassium selenocyanate and vinyl malononitriles was developed for the synthesis of polycyclic selenopyrans via an ultrasound-assisted domino vinylogous nucleophilic reaction/intramolecular selenocyclization/imine-enamine tautomerization reaction. Introducing a simple one-step method and use of available starting materials and mild reaction conditions are the most important advantages of this strategy. Graphical Abstract
{"title":"Ultrasound-assisted a domino three-component reaction to polycyclic selenopyrans synthesis","authors":"Hadi Sedighian, Kaveh Imani, A. Bazgir","doi":"10.1080/10426507.2021.1991344","DOIUrl":"https://doi.org/10.1080/10426507.2021.1991344","url":null,"abstract":"Abstract A novel and efficient three-component reaction of substituted benzoyl chlorides, potassium selenocyanate and vinyl malononitriles was developed for the synthesis of polycyclic selenopyrans via an ultrasound-assisted domino vinylogous nucleophilic reaction/intramolecular selenocyclization/imine-enamine tautomerization reaction. Introducing a simple one-step method and use of available starting materials and mild reaction conditions are the most important advantages of this strategy. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"27 1","pages":"89 - 95"},"PeriodicalIF":0.0,"publicationDate":"2021-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74569867","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}
Pub Date : 2021-10-11DOI: 10.1080/10426507.2021.1987432
R. Shashi, N. Begum
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
{"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}
Pub Date : 2021-10-06DOI: 10.1080/10426507.2021.1986502
Arzu Binici, Aytuğ Okumuş, M. Yakut, Gamze Elmas, Z. Kılıç, Dila Koyunoğlu, L. Açık, H. Simsek
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
{"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}
Pub Date : 2021-07-23DOI: 10.1080/10426507.2021.1945062
Emre Biçer
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
{"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}
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
{"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}
Pub Date : 2021-06-07DOI: 10.1080/10426507.2021.1921775
A. Esmaeili, F. Mesbah, Abbas Moradi, A. Khojastehnezhad, M. Khalili
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
{"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}
Pub Date : 2021-05-21DOI: 10.1080/10426507.2021.1927032
Wafa Arar, A. Khatyr, M. Knorr, Lukas Brieger, A. Krupp, C. Strohmann, M. Efrit, A. Ben Akacha
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
摘要:硫代膦酸酯(EtO)2P(=O)C(=S)N(H)R (L1 R = Cy;通过K[(EtO)2P(=O)]与R - n = C=S的亲核加成制备了L2 R = Bz，并对其进行了晶体学分析。这两种化合物通过强大的分子间N-H···O键成对结合，形成10元超分子大环。这种分子间键也通过L1和L2的Hirshfeld分析进行了研究。L在MeCN溶液中与CuI络合得到双核菱形硫酮配合物[{Cu(μ2-I)2Cu}(η1-L)2] (1a,b)。1a的晶体学表征表明，L1完全通过硫酮函数连接到三角形Cu(I)中心，它们通过一个短的Cu - Cu键(2.6207(4)Å)相互连接。在固体状态下，单个二聚体配合物通过分子间的N-H···O键结合，形成超分子一维带。双核的复合物[{XHg(μ2 X) 2 hgx}(η1 L) 2] (2 X = Br, L = Cy;b X = Br, L = Bz;22c X = I, L = Bz)由L加入HgX2形成。通过x射线衍射研究证实了2b和2c的分子结构，表明单个配合物通过分子间N-H···O键连接，形成超分子一维带。用两种等价物HgBr2处理L1会产生四核化合物[Hg4Br8(κ1-L1)2] 3，其不寻常的溴桥结构已被x射线晶体学阐明。图形抽象
{"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}
Pub Date : 2021-05-18DOI: 10.1080/10426507.2021.1927031
Xinyun Liu, Hang Li, X. Yin
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
{"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}
Pub Date : 2021-05-11DOI: 10.1080/10426507.2021.2012676
M. Karabörk, Ban Abdullelah Muhammed, M. Tümer, Serhan Uruş
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
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