Pub Date : 2019-06-27DOI: 10.1080/10426507.2019.1633319
Shasha Zhang, X. Guo, Yuan Zhou, Yalan Yang, Hao Peng, H. He
Abstract Thirteen novel cyclic phosphates were rationally designed and synthesized by introducing diary ethers containing pyrimidine. All the target compounds were characterized by 1H, 13C, 31P NMR and HRMS. The test of herbicidal activity indicated that most of the compounds showed good herbicidal activities against Amaranthus retroflexus. The compounds IA-2 (1-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)propyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) and IA-3 ((5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)(phenyl)methyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) exhibited remarkable post-emergency herbicidal activity against the tested monocotyledonous weed at the dosage of 112.5 g ai/ha. Graphical Abstract
摘要通过引入含嘧啶的日记醚，合理设计合成了13种新型环状磷酸盐。所有目标化合物均通过1H、13C、31P NMR和HRMS进行了表征。除草活性试验表明，大部分化合物对红苋菜具有良好的除草活性。化合物IA-2(1-(5,5-二甲基-2-氧化-1,3,2-二氧磷-2-基)丙基-2-((4,6-二甲氧磷-2-基)氧)苯甲酸酯)和IA-3((5,5-二甲基-2-氧化-1,3,2-二氧磷-2-基)苯基)甲基-2-((4,6-二甲氧磷-2-基)苯甲酸酯)在112.5 g /ha剂量下对单子叶杂草表现出显著的灾后除草活性。图形抽象
{"title":"Design, synthesis and herbicidal activity of novel cyclic phosphonates with diaryl ethers containing pyrimidine","authors":"Shasha Zhang, X. Guo, Yuan Zhou, Yalan Yang, Hao Peng, H. He","doi":"10.1080/10426507.2019.1633319","DOIUrl":"https://doi.org/10.1080/10426507.2019.1633319","url":null,"abstract":"Abstract Thirteen novel cyclic phosphates were rationally designed and synthesized by introducing diary ethers containing pyrimidine. All the target compounds were characterized by 1H, 13C, 31P NMR and HRMS. The test of herbicidal activity indicated that most of the compounds showed good herbicidal activities against Amaranthus retroflexus. The compounds IA-2 (1-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)propyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) and IA-3 ((5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)(phenyl)methyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) exhibited remarkable post-emergency herbicidal activity against the tested monocotyledonous weed at the dosage of 112.5 g ai/ha. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"9 1","pages":"1158 - 1163"},"PeriodicalIF":0.0,"publicationDate":"2019-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87591122","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 : 2019-06-26DOI: 10.1080/10426507.2019.1633532
R. Mahesh, Rupali Sharma, P. Kour, Anil Kumar
Abstract A cerium(III) chloride-catalysed expeditious synthesis of α-hydroxyphosphonates via a modified Abramov synthetic protocol has been developed. The scope of the current protocol is broad, with a range of aromatic, α,β-unsaturated and heterocyclic aldehydes being efficiently converted to the anticipated products in very good to excellent yields (89–96%) in 15 min using low catalytic loading. The protocol was efficiently extended to hitherto unactivated cyclic ketones such as cyclopentanone and cyclohexanone to afford the required products in excellent yields. However, the reaction with cyclohexenone delivered a Michael product instead of the anticipated α-hydroxyphosphonates. The solvent-free conditions, low catalytic loadings, avoidance of toxic reagents and good to excellent yields are significant advantages of this protocol. Graphical Abstract
{"title":"CeCl3⋅7H2O-catalysed hydrophosphonylation of aldehydes and ketones: An expeditious route to α-hydroxyphosphonates under solvent-free conditions","authors":"R. Mahesh, Rupali Sharma, P. Kour, Anil Kumar","doi":"10.1080/10426507.2019.1633532","DOIUrl":"https://doi.org/10.1080/10426507.2019.1633532","url":null,"abstract":"Abstract A cerium(III) chloride-catalysed expeditious synthesis of α-hydroxyphosphonates via a modified Abramov synthetic protocol has been developed. The scope of the current protocol is broad, with a range of aromatic, α,β-unsaturated and heterocyclic aldehydes being efficiently converted to the anticipated products in very good to excellent yields (89–96%) in 15 min using low catalytic loading. The protocol was efficiently extended to hitherto unactivated cyclic ketones such as cyclopentanone and cyclohexanone to afford the required products in excellent yields. However, the reaction with cyclohexenone delivered a Michael product instead of the anticipated α-hydroxyphosphonates. The solvent-free conditions, low catalytic loadings, avoidance of toxic reagents and good to excellent yields are significant advantages of this protocol. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"32 1","pages":"1091 - 1097"},"PeriodicalIF":0.0,"publicationDate":"2019-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82058469","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 : 2019-06-24DOI: 10.1080/10426507.2019.1618300
H. Chauhan, Nitin Carpenter, S. Bhatiya, S. Joshi
Abstract Seven complexes of type [(C4H9i-O)2PS2]2SbR have been synthesized by the reaction of chlorobis(diisobutyldithiophosphato)antimony(III) with mixed thio and/or oxo donor ligands in 1:1 M stoichiometry, where R = SC6H5, OOCC6H5, SCH2COOH, SOCCH3, OOCCH3, SC6H4COOH and OOC(OH)C6H4. These newly synthesized derivatives have been characterized by different physicochemical (elemental analysis (C, H, S, Sb), melting point, molecular weight determination), spectral (UV, IR, NMR (1H, 13C and 31P)) studies, as well as ESI mass, thermal, powder XRD and biological studies. In the final step of weight loss in thermogravimetric analysis, occurring in the range of 245–505 °C, the degradation of the C6H3CO moieties takes place and antimony sulfide (1/2 Sb2S3) is obtained as remaining material, which is useful in various aspects. Bonded to antimony the diisobutyldithiophosphato substituent behaves as an anisobidentate ligand, which is confirmed through spectral analysis. Powder XRD studies indicate that these compounds crystallize in a monoclinic crystal system with an unit cell volume of ∼7074–7162 Å3 forming nano ranged (9.69–15.69 nm) crystallites. From the antimicrobial screening tests, bis(diisobutyldithiophosphato)antimony(III) thioglycolate (compound 3) has shown a maximum zone of inhibition (19 mm) against E. coli at 200 μg mL−1 concentration. Graphical Abstract
{"title":"Synthesis, characterization, structural elucidation and biological screening of some bis(diisobutyldithiophosphato)antimony(III) complexes","authors":"H. Chauhan, Nitin Carpenter, S. Bhatiya, S. Joshi","doi":"10.1080/10426507.2019.1618300","DOIUrl":"https://doi.org/10.1080/10426507.2019.1618300","url":null,"abstract":"Abstract Seven complexes of type [(C4H9i-O)2PS2]2SbR have been synthesized by the reaction of chlorobis(diisobutyldithiophosphato)antimony(III) with mixed thio and/or oxo donor ligands in 1:1 M stoichiometry, where R = SC6H5, OOCC6H5, SCH2COOH, SOCCH3, OOCCH3, SC6H4COOH and OOC(OH)C6H4. These newly synthesized derivatives have been characterized by different physicochemical (elemental analysis (C, H, S, Sb), melting point, molecular weight determination), spectral (UV, IR, NMR (1H, 13C and 31P)) studies, as well as ESI mass, thermal, powder XRD and biological studies. In the final step of weight loss in thermogravimetric analysis, occurring in the range of 245–505 °C, the degradation of the C6H3CO moieties takes place and antimony sulfide (1/2 Sb2S3) is obtained as remaining material, which is useful in various aspects. Bonded to antimony the diisobutyldithiophosphato substituent behaves as an anisobidentate ligand, which is confirmed through spectral analysis. Powder XRD studies indicate that these compounds crystallize in a monoclinic crystal system with an unit cell volume of ∼7074–7162 Å3 forming nano ranged (9.69–15.69 nm) crystallites. From the antimicrobial screening tests, bis(diisobutyldithiophosphato)antimony(III) thioglycolate (compound 3) has shown a maximum zone of inhibition (19 mm) against E. coli at 200 μg mL−1 concentration. Graphical Abstract","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"1 1","pages":"1116 - 1125"},"PeriodicalIF":0.0,"publicationDate":"2019-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91270208","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 : 2019-05-27DOI: 10.1080/10426507.2019.1627057
G. Keglevich
I am happy to introduce this special issue of Phosphorus, Sulfur, and Silicon and the Related Elements, which presents voluntarily submitted papers from the 22 International Conference on Phosphorus Chemistry (www.icpc22.mke.org. hu) held in Budapest, Hungary from 8–13 July 2018. The venue for the conference was the Hotel Flamenco located in the heart of the Buda part of Budapest (Figure 1). It was a great honor for us, as Hungarian organophosphorus chemists, to have the pleasure of organizing this prestigious event in Hungary. ICPCs are always highly-ranked events held in the past every 3 years, and biannually, more recently. Prestigious gatherings, such as this one remain in great demand, and represent a continuum of high quality during a time when we receive many invitations to predatory conferences. ICPCs are indeed different kinds of events. My first such conference was the 10 ICPC in Bonn organized by
{"title":"Foreword for the special issue of phosphorus, sulfur, and silicon and the related elements dedicated to ICPC 22 – 2018","authors":"G. Keglevich","doi":"10.1080/10426507.2019.1627057","DOIUrl":"https://doi.org/10.1080/10426507.2019.1627057","url":null,"abstract":"I am happy to introduce this special issue of Phosphorus, Sulfur, and Silicon and the Related Elements, which presents voluntarily submitted papers from the 22 International Conference on Phosphorus Chemistry (www.icpc22.mke.org. hu) held in Budapest, Hungary from 8–13 July 2018. The venue for the conference was the Hotel Flamenco located in the heart of the Buda part of Budapest (Figure 1). It was a great honor for us, as Hungarian organophosphorus chemists, to have the pleasure of organizing this prestigious event in Hungary. ICPCs are always highly-ranked events held in the past every 3 years, and biannually, more recently. Prestigious gatherings, such as this one remain in great demand, and represent a continuum of high quality during a time when we receive many invitations to predatory conferences. ICPCs are indeed different kinds of events. My first such conference was the 10 ICPC in Bonn organized by","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"54 1","pages":"270 - 274"},"PeriodicalIF":0.0,"publicationDate":"2019-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78617393","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 : 2019-05-27DOI: 10.1080/10426507.2019.1627055
M. Rudd
{"title":"Foreword for international conference on phosphorus chemistry – ICPC 22","authors":"M. Rudd","doi":"10.1080/10426507.2019.1627055","DOIUrl":"https://doi.org/10.1080/10426507.2019.1627055","url":null,"abstract":"","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"12 1","pages":"269 - 269"},"PeriodicalIF":0.0,"publicationDate":"2019-05-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86782095","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 : 2018-04-19DOI: 10.1080/10426507.2018.1452228
Xiao-yan Li, Q. Kang, Qing-Qing Zhao, Jian-Chun Ma, W. Dong
GRAPHICAL ABSTRACT ABSTRACT Two homotrinuclear Co(II) and Ni(II) complexes, [{CoL(OAc)(DMSO)}2Co]·2DMSO and [{NiL(OAc)(DMSO)}2Ni] have been synthesized by the reaction of 4,4′-dichloro-2,2′-[(1,3-propylene)dioxybis(nitrilomethylidyne)]diphenol (H2L) with cobalt(II) and nickel(II) acetate tetrahydrate in the solution of DMSO, respectively, and characterized by elemental analyses, IR, UV–Vis spectra and X-ray crystallography. In the Co(II) complex, terminal Co2 and Co2#1 atoms located in the N2O2 sites, and are both hexa-coordinated with slightly distorted octahedral geometries. While the central Co1 atom is also hexa-coordinated by six oxygen atoms, four are phenoxy oxygen atoms from two (L)2− units, and two oxygen atoms from µ2-acetate ions, which has formed a octahedral geometry. In the Ni(II) complex, coordination environments of the Ni(II) atoms are similar to those of the Co(II) atoms. Infinite 1D supramolecular structure is formed via abundant intermolecular hydrogen bonding interactions in the Co(II) complex.
{"title":"Dimethylsulfoxide-induced trinuclear Co(II) and Ni(II) salamo-type complexes: Syntheses, crystal structures and spectral properties","authors":"Xiao-yan Li, Q. Kang, Qing-Qing Zhao, Jian-Chun Ma, W. Dong","doi":"10.1080/10426507.2018.1452228","DOIUrl":"https://doi.org/10.1080/10426507.2018.1452228","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT Two homotrinuclear Co(II) and Ni(II) complexes, [{CoL(OAc)(DMSO)}2Co]·2DMSO and [{NiL(OAc)(DMSO)}2Ni] have been synthesized by the reaction of 4,4′-dichloro-2,2′-[(1,3-propylene)dioxybis(nitrilomethylidyne)]diphenol (H2L) with cobalt(II) and nickel(II) acetate tetrahydrate in the solution of DMSO, respectively, and characterized by elemental analyses, IR, UV–Vis spectra and X-ray crystallography. In the Co(II) complex, terminal Co2 and Co2#1 atoms located in the N2O2 sites, and are both hexa-coordinated with slightly distorted octahedral geometries. While the central Co1 atom is also hexa-coordinated by six oxygen atoms, four are phenoxy oxygen atoms from two (L)2− units, and two oxygen atoms from µ2-acetate ions, which has formed a octahedral geometry. In the Ni(II) complex, coordination environments of the Ni(II) atoms are similar to those of the Co(II) atoms. Infinite 1D supramolecular structure is formed via abundant intermolecular hydrogen bonding interactions in the Co(II) complex.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"28 1","pages":"464 - 469"},"PeriodicalIF":0.0,"publicationDate":"2018-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80525406","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 : 2018-04-18DOI: 10.1080/10426507.2018.1452230
Fatemeh Homayoun, Soheila Ghassamipour
GRAPHICAL ABSTRACT ABSTRACT We report a one-pot method for the synthesis of various substituted 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl phosphonate derivatives via phosphorus-carbon bond formation through domino Knoevenagel–phospha–Michael reaction. Multi-walled carbon nanotube‒CO‒NH(CH2)2NH-SO3H was used as an acidic heterogeneous catalyst. The catalyst could be used four times without losing its catalytic activity. The structures of the products were determined by FT-IR spectra, 1H-, 13C- and 31P- Nuclear Magnetic Resonance and elemental analysis. Recovery and reusability of catalyst, simplicity, applicability, good reaction time and good yields of products are the benefits of this work.
{"title":"A domino knoevenagel-phospha-michael reaction: One-pot synthesis of novel organophosphonates in the presence of multi-walled carbon nanotube‒CO‒NH(CH2)2NH-SO3H as catalyst","authors":"Fatemeh Homayoun, Soheila Ghassamipour","doi":"10.1080/10426507.2018.1452230","DOIUrl":"https://doi.org/10.1080/10426507.2018.1452230","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT We report a one-pot method for the synthesis of various substituted 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl phosphonate derivatives via phosphorus-carbon bond formation through domino Knoevenagel–phospha–Michael reaction. Multi-walled carbon nanotube‒CO‒NH(CH2)2NH-SO3H was used as an acidic heterogeneous catalyst. The catalyst could be used four times without losing its catalytic activity. The structures of the products were determined by FT-IR spectra, 1H-, 13C- and 31P- Nuclear Magnetic Resonance and elemental analysis. Recovery and reusability of catalyst, simplicity, applicability, good reaction time and good yields of products are the benefits of this work.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"24 1","pages":"475 - 480"},"PeriodicalIF":0.0,"publicationDate":"2018-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79199146","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 : 2018-03-14DOI: 10.1080/10426507.2018.1452229
Sk. Nayab Rasool, Ch. Subramanyam, D. B. Janakiramudu, P. Supraja, R. Usha, C. N. Raju
GRAPHICAL ABSTRACT ABSTRACT A series of new phosphoramidates and phosphonates were synthesized in single step by reacting diethyl phosphorochloridate with various bioactive amines. The newly synthesized compounds 3a-j were tested for antibacterial activity against Gram-positive and Gram-negative bacteria. All the title compounds exhibited good activity. Amongst all the tested compounds, 3b (diethyl(4-(6-fluorobenzo(d)isoxazol-3-yl)piperidin-1-yl)phosphonate), 3c (diethyl 4, 6-difluorobenzo(d)thiazole-2-ylphosphoramidate) and 3d (diethyl 5-nitro-1H-indazol-1-yl- phosphonate) displayed promising antimicrobial activity against Pseudomonas aeruginosa and Trichoderma viride due to the presence of electron with drawing fluoro and nitro groups respectively.
{"title":"Convenient one-pot synthesis and biological evaluation of phosphoramidates and phosphonates containing heterocycles","authors":"Sk. Nayab Rasool, Ch. Subramanyam, D. B. Janakiramudu, P. Supraja, R. Usha, C. N. Raju","doi":"10.1080/10426507.2018.1452229","DOIUrl":"https://doi.org/10.1080/10426507.2018.1452229","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A series of new phosphoramidates and phosphonates were synthesized in single step by reacting diethyl phosphorochloridate with various bioactive amines. The newly synthesized compounds 3a-j were tested for antibacterial activity against Gram-positive and Gram-negative bacteria. All the title compounds exhibited good activity. Amongst all the tested compounds, 3b (diethyl(4-(6-fluorobenzo(d)isoxazol-3-yl)piperidin-1-yl)phosphonate), 3c (diethyl 4, 6-difluorobenzo(d)thiazole-2-ylphosphoramidate) and 3d (diethyl 5-nitro-1H-indazol-1-yl- phosphonate) displayed promising antimicrobial activity against Pseudomonas aeruginosa and Trichoderma viride due to the presence of electron with drawing fluoro and nitro groups respectively.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"14 1","pages":"470 - 474"},"PeriodicalIF":0.0,"publicationDate":"2018-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75254868","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 : 2018-03-06DOI: 10.1080/10426507.2018.1436545
Efeturi A. Onoabedje, Obioma Chinwe Chinwuko, B. Ezema, M. A. Ezeokonkwo
GRAPHICAL ABSTRACT ABSTRACT A convenient synthesis of new polycyclic mixed phenothiazine-phenoxazine compounds is described. The cross-coupling of 2,4-diaminothiophenol with 2,3-dichloro-1,4-naphthoquin one at room temperature gave reddish brown 10-amino-6-chlorobenzo[a]phenoxazin-5-one which was converted into a benzoxazinophenothiazin-12-amine in 58% yield via reaction with 2-aminothiophenol under anhydrous basic conditions. A three-component one-pot synthesis improved the yield of benzoxazinophenothia-12-amine to 81% a in shorter time compared to two steps reactions. The synthesis of new azomethine derivatives of benzo[a]benzo[5,6] [1,4] oxazino [3,2-c] phenothiazin-12-amine with extended conjugations and excellent yields were also reported. The structural assignments of the prepared compounds were established by combine Ultraviolet-Visible, Fourier Transform Infrared, 1H and 13C Nuclear Magnetic Resonance Spectroscopies, Mass Spectrometry and elemental analytical data. The ease of preparations in high yields and their intense colourations make these compounds applicable as dyestuffs.
{"title":"Synthesis of polycyclic mixed phenothiazine-phenoxazine organic dyes","authors":"Efeturi A. Onoabedje, Obioma Chinwe Chinwuko, B. Ezema, M. A. Ezeokonkwo","doi":"10.1080/10426507.2018.1436545","DOIUrl":"https://doi.org/10.1080/10426507.2018.1436545","url":null,"abstract":"GRAPHICAL ABSTRACT ABSTRACT A convenient synthesis of new polycyclic mixed phenothiazine-phenoxazine compounds is described. The cross-coupling of 2,4-diaminothiophenol with 2,3-dichloro-1,4-naphthoquin one at room temperature gave reddish brown 10-amino-6-chlorobenzo[a]phenoxazin-5-one which was converted into a benzoxazinophenothiazin-12-amine in 58% yield via reaction with 2-aminothiophenol under anhydrous basic conditions. A three-component one-pot synthesis improved the yield of benzoxazinophenothia-12-amine to 81% a in shorter time compared to two steps reactions. The synthesis of new azomethine derivatives of benzo[a]benzo[5,6] [1,4] oxazino [3,2-c] phenothiazin-12-amine with extended conjugations and excellent yields were also reported. The structural assignments of the prepared compounds were established by combine Ultraviolet-Visible, Fourier Transform Infrared, 1H and 13C Nuclear Magnetic Resonance Spectroscopies, Mass Spectrometry and elemental analytical data. The ease of preparations in high yields and their intense colourations make these compounds applicable as dyestuffs.","PeriodicalId":20043,"journal":{"name":"Phosphorus Sulfur and Silicon and The Related Elements","volume":"38 1","pages":"437 - 442"},"PeriodicalIF":0.0,"publicationDate":"2018-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82313734","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 : 2018-02-26DOI: 10.1080/10426507.2018.1436546
Jin-Lin Wan, Yiyuan Gan, Wei-nan Hu, Jiao Meng, Kun Tian, Xiao-qin Li, Shou-Qun Wu, Yang Xu, Gui-ping Ouyang, Zhenchao Wang
GRAPHICAL ABSTRACT ABSTRACT Novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety were prepared and evaluated for their anti-bacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) by performing a turbidimetre test. The products were structurally characterised by IR, 1H NMR, 13C NMR, 19F NMR and HRMS. Anti-bacterial testing showed that most of the evaluated compounds (6a-6s) exhibited excellent activity (≥74.19%) against Xoo at a concentration of 200 µg/mL, with 50% effective concentration (EC50) values ranging from 12.21 to 67.20 µg/mL, which were superior to the commercial antibacterial agent bismerthiazol (92.23 µg/mL). Among them, compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((2-chlorobenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6b) demonstrated good inhibitory activity against Xac (89.46% at 200 µg/mL) and Xoo (EC50 = 18.28 µg/mL); compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((4-methoxybenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6g) displayed excellent activity against Xoo with EC50 value of 12.21 µg/mL.
摘要本文制备了含有缩氨基脲基团的新型1,3,4-噻二唑衍生物，并对其抑菌活性进行了评价。稻瘟病菌(Xoo)和轴尾黄单胞菌(Xanthomonas axonopodis pv)。柠檬酸(Xac)进行浊度计试验。通过IR、1H NMR、13C NMR、19F NMR和HRMS对产物进行了结构表征。抑菌试验结果表明，大部分化合物(6a-6s)在200µg/mL的浓度下对Xoo具有良好的抑菌活性(≥74.19%)，50%有效浓度(EC50)在12.21 ~ 67.20µg/mL之间，优于市售抗菌剂双硫噻唑(92.23µg/mL)。其中，化合物2-((2-氯- 1h -吲哚-3-基)亚甲基)- n -(5-(2-氯苯基)硫)-1,3,4-噻二唑-2-基)肼-1-羧酰胺(6b)对Xac和Xoo具有良好的抑制活性(200µg/mL时为89.46%)(EC50 = 18.28µg/mL);化合物2-((2-氯- 1h -吲哚-3-基)亚甲基)- n -(5-(4-甲氧基苄基)硫)-1,3,4-噻二唑-2-基)肼-1-羧酰胺(6g)对Xoo具有良好的抑菌活性，EC50值为12.21µg/mL。
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