Pub Date : 2020-11-24DOI: 10.1080/10426507.2020.1854258
G. Sravya, A. Balakrishna, G. Zyryanov, G. Mohan, C. S. Reddy, N. Bakthavatchala Reddy
Abstract The review discusses recent achievements in the development of more ecofriendly and economically viable processes for the synthesis of biologically potent α-aminophosphonates via Kabachnik-Fields reaction by three-component coupling of carbonyl, amine and hydrophosphoryl compounds. These α-aminophosphonates exhibited promising antioxidant, antimicrobial and anticancer activity. Some recent developments on the synthesis of biologically active α-aminophosphonates in the presence of various catalysts, in catalytic solvent medium, in catalyst-free solvent medium, under solvent-free conditions, and reactions in solution are discussed. Miscellaneous reactions are also included. Graphical Abstract
{"title":"Synthesis of α-aminophosphonates by the Kabachnik-Fields reaction","authors":"G. Sravya, A. Balakrishna, G. Zyryanov, G. Mohan, C. S. Reddy, N. Bakthavatchala Reddy","doi":"10.1080/10426507.2020.1854258","DOIUrl":"https://doi.org/10.1080/10426507.2020.1854258","url":null,"abstract":"Abstract The review discusses recent achievements in the development of more ecofriendly and economically viable processes for the synthesis of biologically potent α-aminophosphonates via Kabachnik-Fields reaction by three-component coupling of carbonyl, amine and hydrophosphoryl compounds. These α-aminophosphonates exhibited promising antioxidant, antimicrobial and anticancer activity. Some recent developments on the synthesis of biologically active α-aminophosphonates in the presence of various catalysts, in catalytic solvent medium, in catalyst-free solvent medium, under solvent-free conditions, and reactions in solution are discussed. Miscellaneous reactions are also included. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"2 1","pages":"353 - 381"},"PeriodicalIF":0.0,"publicationDate":"2020-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75394635","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 : 2020-11-12DOI: 10.1080/10426507.2020.1845680
Roqayeh Khadem Moghaddam, Ghasem Aghapour
Abstract A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry. Graphical Abstract
{"title":"One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system","authors":"Roqayeh Khadem Moghaddam, Ghasem Aghapour","doi":"10.1080/10426507.2020.1845680","DOIUrl":"https://doi.org/10.1080/10426507.2020.1845680","url":null,"abstract":"Abstract A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"73 2 1","pages":"398 - 406"},"PeriodicalIF":0.0,"publicationDate":"2020-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72677590","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 : 2020-11-10DOI: 10.1080/10426507.2020.1845679
Sk. Md. Altaff, T. Raja Rajeswari, Ch. Subramanyam
Abstract We have synthesized a series of phosphoramidates containing a heterocyclic moiety with good yields (88–95%) by the reaction of (E)-5-benzylidene-3-((2-hydroxyethoxy)methyl)thiazolidine-2,4-dione with ethyl phosphorodichloridate followed by the reaction with various heterocyclic amines. The designed compounds were primarily screened for their ability to inhibit pancreatic α-amylase enzyme using in silico molecular docking approach. The compounds with good binding energies (−8.0 to −6.9 kcal/mol) when compared with standard drug, acarbose (−8.0 kcal/mol) were prompted for the synthesis. The structures of the newly prepared compounds were confirmed by their spectroscopic analyses. They were further screened in vitro for their inhibition toward α-amylase enzyme using acarbose as standard drug. All compounds exhibited moderate to good inhibition potential with IC50 values in the range of 54.14 ± 0.35 to 185.04 ± 0.53 µg/mL when compared with the standard drug (IC50, 50.47 ± 0.28 µg/mL). Especially, the compound (E)-2-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methoxy)ethyl ethyl 1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylphosphoramidate (6f) (IC50, 54.14 ± 0.35 µg/mL) and (E)-2-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methoxy)ethyl ethyl benzo[d]thiazol-2-ylphosphoramidate (6c) (IC50, 57.02 ± 0.32 µg/mL) exhibited the best inhibition among the synthesized compounds. Graphical abstract
{"title":"Synthesis, α-amylase inhibitory activity evaluation and in silico molecular docking study of some new phosphoramidates containing heterocyclic ring","authors":"Sk. Md. Altaff, T. Raja Rajeswari, Ch. Subramanyam","doi":"10.1080/10426507.2020.1845679","DOIUrl":"https://doi.org/10.1080/10426507.2020.1845679","url":null,"abstract":"Abstract We have synthesized a series of phosphoramidates containing a heterocyclic moiety with good yields (88–95%) by the reaction of (E)-5-benzylidene-3-((2-hydroxyethoxy)methyl)thiazolidine-2,4-dione with ethyl phosphorodichloridate followed by the reaction with various heterocyclic amines. The designed compounds were primarily screened for their ability to inhibit pancreatic α-amylase enzyme using in silico molecular docking approach. The compounds with good binding energies (−8.0 to −6.9 kcal/mol) when compared with standard drug, acarbose (−8.0 kcal/mol) were prompted for the synthesis. The structures of the newly prepared compounds were confirmed by their spectroscopic analyses. They were further screened in vitro for their inhibition toward α-amylase enzyme using acarbose as standard drug. All compounds exhibited moderate to good inhibition potential with IC50 values in the range of 54.14 ± 0.35 to 185.04 ± 0.53 µg/mL when compared with the standard drug (IC50, 50.47 ± 0.28 µg/mL). Especially, the compound (E)-2-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methoxy)ethyl ethyl 1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-ylphosphoramidate (6f) (IC50, 54.14 ± 0.35 µg/mL) and (E)-2-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methoxy)ethyl ethyl benzo[d]thiazol-2-ylphosphoramidate (6c) (IC50, 57.02 ± 0.32 µg/mL) exhibited the best inhibition among the synthesized compounds. Graphical abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"32 1","pages":"389 - 397"},"PeriodicalIF":0.0,"publicationDate":"2020-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84393484","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 : 2020-11-07DOI: 10.1080/10426507.2020.1845682
Sabrieh Lashkari, M. Shahraki, Mahdieh Darijani, F. Mahmoudi
Abstract The [4 + 2] cycloaddition reaction (McCormack reaction) of 1,3-butadiene with dichloromethylphosphine (DCMP) yielding 3-phospholene oxide has been studied by density functional theory (DFT) at the M06-2x/6-311++G(2d,2p) computational level. This reaction is a cheletropic process that comprises two steps with the formation an ionic intermediate in the first step and subsequently, its hydrolysis, in the second step. For the first step of this reaction, three paths were considered as a stepwise pathway with a diradical intermediate and an assumed path with a trigonal intermediate that compared with the concerted path in terms of energy. Analysis of the reactivity indices showed that the 1,3-butadiene and DCMP behaved as nucleophile and electrophile, respectively. Graphical abstract
{"title":"A density functional theory study of the synthesis of 3-phospholene oxide through the McCormack cycloaddition reaction","authors":"Sabrieh Lashkari, M. Shahraki, Mahdieh Darijani, F. Mahmoudi","doi":"10.1080/10426507.2020.1845682","DOIUrl":"https://doi.org/10.1080/10426507.2020.1845682","url":null,"abstract":"Abstract The [4 + 2] cycloaddition reaction (McCormack reaction) of 1,3-butadiene with dichloromethylphosphine (DCMP) yielding 3-phospholene oxide has been studied by density functional theory (DFT) at the M06-2x/6-311++G(2d,2p) computational level. This reaction is a cheletropic process that comprises two steps with the formation an ionic intermediate in the first step and subsequently, its hydrolysis, in the second step. For the first step of this reaction, three paths were considered as a stepwise pathway with a diradical intermediate and an assumed path with a trigonal intermediate that compared with the concerted path in terms of energy. Analysis of the reactivity indices showed that the 1,3-butadiene and DCMP behaved as nucleophile and electrophile, respectively. Graphical abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"33 1","pages":"414 - 421"},"PeriodicalIF":0.0,"publicationDate":"2020-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79749870","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 : 2020-10-20DOI: 10.1080/10426507.2020.1831499
S. Amin, M. M. Alam, M. Akhter, A. Najmi, N. Siddiqui, A. Husain, Mohammed Shaquiquzzaman
Abstract Phosphorus oxychloride, POCl3, an important phosphorus compound, has diverse applications in synthetic chemistry. It plays an important role in chlorination, Vilsmeier Haack reaction, dehydration and cyclization which have been highlighted here. Moreover, different reaction conditions implied and reported in the literature along with the general mechanism are provided briefly in this review. This review provides an insight into the recent applications of phosphorus oxychloride as a reagent in organic syntheses in the last two year i.e. 2018–19. Graphic abstract
{"title":"A review on synthetic procedures and applications of phosphorus oxychloride (POCl3) in the last biennial period (2018–19)","authors":"S. Amin, M. M. Alam, M. Akhter, A. Najmi, N. Siddiqui, A. Husain, Mohammed Shaquiquzzaman","doi":"10.1080/10426507.2020.1831499","DOIUrl":"https://doi.org/10.1080/10426507.2020.1831499","url":null,"abstract":"Abstract Phosphorus oxychloride, POCl3, an important phosphorus compound, has diverse applications in synthetic chemistry. It plays an important role in chlorination, Vilsmeier Haack reaction, dehydration and cyclization which have been highlighted here. Moreover, different reaction conditions implied and reported in the literature along with the general mechanism are provided briefly in this review. This review provides an insight into the recent applications of phosphorus oxychloride as a reagent in organic syntheses in the last two year i.e. 2018–19. Graphic abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"59 1","pages":"211 - 274"},"PeriodicalIF":0.0,"publicationDate":"2020-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84922726","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 : 2020-05-03DOI: 10.1080/10426507.2019.1708360
M. Melnik, P. Mikuš
Abstract In this review, the structural data of monomeric platinum(II) complexes with inner coordination spheres of Pt(η2-P2L)(SiL)2, Pt(η2-P2L)(η2-Si2L) and Pt(η2-P,SiL)2 are classified and analyzed. These complexes crystallize in three crystal systems: monoclinic (8 examples), triclinic (4 examples) and orthorhombic (4 examples). Distorted square-planar environments about the Pt(II) atoms are built up by combination of homobi-P,P with two monodentate Si donor ligands; homobi-PP with homo-Si,Si donor ligands, or heterobi-P,Si donor ligands. The chelating ligands create metallacycles with the following angles: 65.0° (SiOSi) < 83.1° (SiC2Si) < 85.2° (PC2P) < 88.8° (SiSi2Si)). The mean Pt-P and Pt-Si bond distances in Pt(η2-P2L)·(SiL)2 complexes are 2.319 and 2.365 Å; in Pt(η2-P2L)(η2-Si2L) the values are 2.316 and 2.360 Å. The complex [Pt{η2-Me2P(C2B10H10)SiMe2}2] exists in two isomeric forms, a monoclinic cis- and a triclinic trans-isomer. The structural data are compared and discussed with the complexes of inner coordination spheres: Pt(η2-P2L)(XL)2 (X = O, N, CN, BL, Cl, SL, SeL, Br, or I) and Pt(η2-P2L)(η2-X2L) (X = OL, NL, SL or SeL). Graphical Abstract
{"title":"Organophosphines in PtP2Si2 derivatives – structural aspects","authors":"M. Melnik, P. Mikuš","doi":"10.1080/10426507.2019.1708360","DOIUrl":"https://doi.org/10.1080/10426507.2019.1708360","url":null,"abstract":"Abstract In this review, the structural data of monomeric platinum(II) complexes with inner coordination spheres of Pt(η2-P2L)(SiL)2, Pt(η2-P2L)(η2-Si2L) and Pt(η2-P,SiL)2 are classified and analyzed. These complexes crystallize in three crystal systems: monoclinic (8 examples), triclinic (4 examples) and orthorhombic (4 examples). Distorted square-planar environments about the Pt(II) atoms are built up by combination of homobi-P,P with two monodentate Si donor ligands; homobi-PP with homo-Si,Si donor ligands, or heterobi-P,Si donor ligands. The chelating ligands create metallacycles with the following angles: 65.0° (SiOSi) < 83.1° (SiC2Si) < 85.2° (PC2P) < 88.8° (SiSi2Si)). The mean Pt-P and Pt-Si bond distances in Pt(η2-P2L)·(SiL)2 complexes are 2.319 and 2.365 Å; in Pt(η2-P2L)(η2-Si2L) the values are 2.316 and 2.360 Å. The complex [Pt{η2-Me2P(C2B10H10)SiMe2}2] exists in two isomeric forms, a monoclinic cis- and a triclinic trans-isomer. The structural data are compared and discussed with the complexes of inner coordination spheres: Pt(η2-P2L)(XL)2 (X = O, N, CN, BL, Cl, SL, SeL, Br, or I) and Pt(η2-P2L)(η2-X2L) (X = OL, NL, SL or SeL). Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"12 1","pages":"367 - 370"},"PeriodicalIF":0.0,"publicationDate":"2020-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85793428","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 : 2020-05-03DOI: 10.1080/10426507.2019.1700412
Tianfeng Cai, Yueru Tian, Jie Zhang
Abstract A series of heterojunction catalysts (CuCN-X) were successfully fabricated by loading the different amounts of Keggin type Cu mono-substituted heteropoly acid (HPW11Cu) on the surface of hollow nanospheres g-C3N4 (HSCN). The HSCNs were prepared by using SiO2 as a hard template. The chemical structure, porosity, morphology and electronic property of the prepared catalysts were investigated using XRD, SEM, N2-absorption isotherm and XPS. The results indicated that the modified HSCN show prominent absorption in the visible light range and decrease the band gap. The greatly enhanced photocatalytic activity of obtained CuCN-X have been shown by the degradation of Rhodamine B (RhB), reduction of CO2 and production of photocatalytic hydrogen under visible light irradiation. More significantly, CuCN-15 has shown significantly improved photocatalytic performance at 4.5, 3.5 and 3.3 times higher that of than HSCN for the degradation of RhB, reduction of CO2 and production of photocatalytic hydrogen, respectively. Furthermore, the mechanism for the enhanced photocatalytic activity of CuCN-X is proposed to be due to the formation of heterojunction. The electrons can be rapidly transferred from HSCN to HPW11Cu, in which facilitate charge separation and charge transfer. Graphical Abstract
{"title":"Preparation of hollow nanospheres g-C3N4 loaded by Keggin type Cu mono-substituted heteropoly acid with enhanced visible-light harvesting and electron transfer properties for high-efficiency photocatalysis","authors":"Tianfeng Cai, Yueru Tian, Jie Zhang","doi":"10.1080/10426507.2019.1700412","DOIUrl":"https://doi.org/10.1080/10426507.2019.1700412","url":null,"abstract":"Abstract A series of heterojunction catalysts (CuCN-X) were successfully fabricated by loading the different amounts of Keggin type Cu mono-substituted heteropoly acid (HPW11Cu) on the surface of hollow nanospheres g-C3N4 (HSCN). The HSCNs were prepared by using SiO2 as a hard template. The chemical structure, porosity, morphology and electronic property of the prepared catalysts were investigated using XRD, SEM, N2-absorption isotherm and XPS. The results indicated that the modified HSCN show prominent absorption in the visible light range and decrease the band gap. The greatly enhanced photocatalytic activity of obtained CuCN-X have been shown by the degradation of Rhodamine B (RhB), reduction of CO2 and production of photocatalytic hydrogen under visible light irradiation. More significantly, CuCN-15 has shown significantly improved photocatalytic performance at 4.5, 3.5 and 3.3 times higher that of than HSCN for the degradation of RhB, reduction of CO2 and production of photocatalytic hydrogen, respectively. Furthermore, the mechanism for the enhanced photocatalytic activity of CuCN-X is proposed to be due to the formation of heterojunction. The electrons can be rapidly transferred from HSCN to HPW11Cu, in which facilitate charge separation and charge transfer. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"1 1","pages":"399 - 408"},"PeriodicalIF":0.0,"publicationDate":"2020-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82981489","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 : 2020-05-03DOI: 10.1080/10426507.2019.1700376
V. Uvarov, D. A. de Vekki
Abstract Using a “chiral pool” approach, a number of chiral thiolate and sulfide ligands based on natural terpenes and terpenoids have been synthesized in a few simple steps. Two new Rh-thiolate complexes with the formula [Rh(CO)2(μ-SR)]2 were obtained. The influence of these complexes and catalytic systems formed by combining the synthesized ligands with [Rh(CO)2(μ-Cl)]2 and [Rh(cod)(μ-Cl)]2, on the reaction rate, chemoselectivity, stereoselectivity and formation of tetraphenyldisiloxane in Rh-catalyzed asymmetric hydrosilylation of acetophenone as a model reaction have been studied. Mechanistic aspects of formation of silyl enol ether as a side product in the presence of S-containing ligands are presented. Graphical Abstract
{"title":"First study of rhodium(I) complexes with chiral sulfur-containing terpenoids as catalytic systems for ketone hydrosilylation","authors":"V. Uvarov, D. A. de Vekki","doi":"10.1080/10426507.2019.1700376","DOIUrl":"https://doi.org/10.1080/10426507.2019.1700376","url":null,"abstract":"Abstract Using a “chiral pool” approach, a number of chiral thiolate and sulfide ligands based on natural terpenes and terpenoids have been synthesized in a few simple steps. Two new Rh-thiolate complexes with the formula [Rh(CO)2(μ-SR)]2 were obtained. The influence of these complexes and catalytic systems formed by combining the synthesized ligands with [Rh(CO)2(μ-Cl)]2 and [Rh(cod)(μ-Cl)]2, on the reaction rate, chemoselectivity, stereoselectivity and formation of tetraphenyldisiloxane in Rh-catalyzed asymmetric hydrosilylation of acetophenone as a model reaction have been studied. Mechanistic aspects of formation of silyl enol ether as a side product in the presence of S-containing ligands are presented. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"10 4 1","pages":"376 - 387"},"PeriodicalIF":0.0,"publicationDate":"2020-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82705136","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 : 2020-05-03DOI: 10.1080/10426507.2019.1700260
Hui Li, Aoyun Lu, Yanqiu Zhang, Yanqing Peng, G. Song
Abstract To explore a new skeleton with nematicidal activity, a series of novel azabicyclo derivatives containing a thiazole moiety were designed, synthesized and evaluated for their nematicidal activities. The bioassay results against pine-wood nematodes (Bursaphelenchus xylophilus) showed that most of the title compounds displayed nematicidal activity at a concentration of 40 mg/L. Especially, the title compounds2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)oxy)-4-(4-chlorophenyl)thiazole (7e), 2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)-4-phenylthiazole (10a) and 2-((8-methyl-8-azabicyclo [3.2.1]octan-3-yl)thio)-4-(4-chlorophenyl)thiazole (10e) exhibited more than 90% mortality against Bursaphelenchus xylophilus. Graphical Abstract
{"title":"Synthesis of novel azabicyclo derivatives containing a thiazole moiety and their biological activity against pine-wood nematodes","authors":"Hui Li, Aoyun Lu, Yanqiu Zhang, Yanqing Peng, G. Song","doi":"10.1080/10426507.2019.1700260","DOIUrl":"https://doi.org/10.1080/10426507.2019.1700260","url":null,"abstract":"Abstract To explore a new skeleton with nematicidal activity, a series of novel azabicyclo derivatives containing a thiazole moiety were designed, synthesized and evaluated for their nematicidal activities. The bioassay results against pine-wood nematodes (Bursaphelenchus xylophilus) showed that most of the title compounds displayed nematicidal activity at a concentration of 40 mg/L. Especially, the title compounds2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)oxy)-4-(4-chlorophenyl)thiazole (7e), 2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)-4-phenylthiazole (10a) and 2-((8-methyl-8-azabicyclo [3.2.1]octan-3-yl)thio)-4-(4-chlorophenyl)thiazole (10e) exhibited more than 90% mortality against Bursaphelenchus xylophilus. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"20 4 1","pages":"371 - 375"},"PeriodicalIF":0.0,"publicationDate":"2020-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83540889","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 : 2020-05-03DOI: 10.1080/10426507.2019.1700415
Siti Syaida Sirat, Hafiz Malik Hussien Abdelnasir, O. Shawkataly
Abstract The solid-state structures of compounds PPh2CH2SPh (1) and PPh2C6H4SMe (2) were determined by single crystal X-ray diffraction. Experimental results on the molecular structures of compounds 1 and 2 were supported by Hirshfeld surface analysis and Density Functional Theory (DFT). The computed values calculated at DFT level using B3LYP function with 6-311++G (3df, 3pd) (P, S) and 6-31G* (C, H) basis sets are in good agreement with the experimental results. Graphical Abstract
{"title":"A combined X-ray crystallography and theoretical study of PPh2CH2SPh and PPh2C6H4SMe ligands","authors":"Siti Syaida Sirat, Hafiz Malik Hussien Abdelnasir, O. Shawkataly","doi":"10.1080/10426507.2019.1700415","DOIUrl":"https://doi.org/10.1080/10426507.2019.1700415","url":null,"abstract":"Abstract The solid-state structures of compounds PPh2CH2SPh (1) and PPh2C6H4SMe (2) were determined by single crystal X-ray diffraction. Experimental results on the molecular structures of compounds 1 and 2 were supported by Hirshfeld surface analysis and Density Functional Theory (DFT). The computed values calculated at DFT level using B3LYP function with 6-311++G (3df, 3pd) (P, S) and 6-31G* (C, H) basis sets are in good agreement with the experimental results. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"1 1","pages":"429 - 436"},"PeriodicalIF":0.0,"publicationDate":"2020-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73334685","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}
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