Bakr F. Abdel-Wahab, A. Mabied, J. Fettinger, Ahmed H. E. Hassan, A. Farahat
A promising imidazole compound was synthesized through the following route. The reaction of 5-methyl-2-phenyl-1H-imidazole-4-carbohydrazide (1) with carbon disulfide and potassium hydroxide in ethanol (80%) afforded potassium salt (2). Refluxing of (2) with phenacyl bromide (3) in ethanol/water (1:1) gave 2-((5-(5-methyl-2-phenyl-1H-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one (4) in a 76% yield. The structure of the title heterocycle (4) was confirmed by single-crystal X-ray diffraction and nuclear magnetic resonance.
{"title":"2-((5-(5-Methyl-2-phenyl-1H-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one","authors":"Bakr F. Abdel-Wahab, A. Mabied, J. Fettinger, Ahmed H. E. Hassan, A. Farahat","doi":"10.3390/m1666","DOIUrl":"https://doi.org/10.3390/m1666","url":null,"abstract":"A promising imidazole compound was synthesized through the following route. The reaction of 5-methyl-2-phenyl-1H-imidazole-4-carbohydrazide (1) with carbon disulfide and potassium hydroxide in ethanol (80%) afforded potassium salt (2). Refluxing of (2) with phenacyl bromide (3) in ethanol/water (1:1) gave 2-((5-(5-methyl-2-phenyl-1H-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one (4) in a 76% yield. The structure of the title heterocycle (4) was confirmed by single-crystal X-ray diffraction and nuclear magnetic resonance.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41520283","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}
Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki, Gamal A. El-Hiti
The reaction of a 1:1 mixture of 3-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (1) and 2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (2) in anhydrous ethanol containing piperidine as a catalyst under reflux for 4 h gave (2Z,5Z)-5-((3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (3), C34H24N4O3F, in 82% yield. The structure of the newly synthesized heterocycle was confirmed via X-ray diffraction and spectral analyses.
{"title":"(2Z,5Z)-5-((3-(Benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one","authors":"Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki, Gamal A. El-Hiti","doi":"10.3390/m1665","DOIUrl":"https://doi.org/10.3390/m1665","url":null,"abstract":"The reaction of a 1:1 mixture of 3-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde (1) and 2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (2) in anhydrous ethanol containing piperidine as a catalyst under reflux for 4 h gave (2Z,5Z)-5-((3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one (3), C34H24N4O3F, in 82% yield. The structure of the newly synthesized heterocycle was confirmed via X-ray diffraction and spectral analyses.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45795728","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}
Shakira I. Colon-Madera, Abby R. Jennings, Scott T. Iacono, Gary J. Balaich
Reaction of triplet O2 with the bridged dipotassium dicyclopentadienyl salt, ansa-[(CHBut)2(Ph2C5H2)2]K2(THF)3 1, in dry MeCN facilitated an intramolecular cyclopentadienyl ring-C to ring-C bond formation and the precipitation of the crude product 4,5-di-tert-butyl-1,3,6,8-tetraphenyl-4,5,8a,8b-tetrahydro-as-indacene 2 as an off-white solid in a 73% yield (>95% pure, 1H NMR). Characterization of 2 was carried out using multinuclear NMR spectroscopy (1H and 13C), single-crystal X-ray crystallography, FTIR spectroscopy, and thermal analytical techniques (SDT, DSC). The molecular structure consisted of a rigid, C2-symmetric six-membered ring in a chair conformation with four of the ring-C atoms fused to 1,3-diphenylcyclopentadiene rings and the other two ring-C atoms substituted with trans di-axial But groups.
{"title":"4,5-Di-tert-butyl-1,3,6,8-tetraphenyl-4,5,8a,8b-tetrahydro-as-indacene","authors":"Shakira I. Colon-Madera, Abby R. Jennings, Scott T. Iacono, Gary J. Balaich","doi":"10.3390/m1663","DOIUrl":"https://doi.org/10.3390/m1663","url":null,"abstract":"Reaction of triplet O2 with the bridged dipotassium dicyclopentadienyl salt, ansa-[(CHBut)2(Ph2C5H2)2]K2(THF)3 1, in dry MeCN facilitated an intramolecular cyclopentadienyl ring-C to ring-C bond formation and the precipitation of the crude product 4,5-di-tert-butyl-1,3,6,8-tetraphenyl-4,5,8a,8b-tetrahydro-as-indacene 2 as an off-white solid in a 73% yield (>95% pure, 1H NMR). Characterization of 2 was carried out using multinuclear NMR spectroscopy (1H and 13C), single-crystal X-ray crystallography, FTIR spectroscopy, and thermal analytical techniques (SDT, DSC). The molecular structure consisted of a rigid, C2-symmetric six-membered ring in a chair conformation with four of the ring-C atoms fused to 1,3-diphenylcyclopentadiene rings and the other two ring-C atoms substituted with trans di-axial But groups.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"56 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135449411","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. Aragoni, V. Lippolis, A. Mancini, Anna Pintus, E. Podda, J. Orton, S. Coles, M. Arca
2-(5,6-diphenyl-1,2,4-triazin-3-yl)pyridinium dichloroiodate (I) (1) was synthesized by reacting 3-(2-pyridyl)-5,6-diphenyl-1,2,4-triazine with ICl in dichloromethane solution. The structural characterization of 1 by SC-XRD analysis was accompanied by elemental analysis, FT-IR, and FT-Raman spectroscopy measurements.
{"title":"2-(5,6-Diphenyl-1,2,4-Triazin-3-yl)pyridinium Dichloroiodate (I)","authors":"M. Aragoni, V. Lippolis, A. Mancini, Anna Pintus, E. Podda, J. Orton, S. Coles, M. Arca","doi":"10.3390/m1662","DOIUrl":"https://doi.org/10.3390/m1662","url":null,"abstract":"2-(5,6-diphenyl-1,2,4-triazin-3-yl)pyridinium dichloroiodate (I) (1) was synthesized by reacting 3-(2-pyridyl)-5,6-diphenyl-1,2,4-triazine with ICl in dichloromethane solution. The structural characterization of 1 by SC-XRD analysis was accompanied by elemental analysis, FT-IR, and FT-Raman spectroscopy measurements.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45004628","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}
Lingsen Li, Jingjing Wang, Tianhao Gong, Kunming Liu, Juanhua Li
In this short note, we elaborate on a synthetic method for a new terpyridine Schiff base-bearing vanillin motif. The structure of the product was confirmed via 1H and 13C-NMR spectroscopy and FT-IR spectroscopy. Due to the peculiar coordination nature and optical property of the synthesized compound, this work presents a promising colorimetric sensing molecular compound.
{"title":"2-(((4-([2,2′:6′,2″-Terpyridin]-4′-yl)phenyl)imino)methyl)-6-methoxyphenol","authors":"Lingsen Li, Jingjing Wang, Tianhao Gong, Kunming Liu, Juanhua Li","doi":"10.3390/m1664","DOIUrl":"https://doi.org/10.3390/m1664","url":null,"abstract":"In this short note, we elaborate on a synthetic method for a new terpyridine Schiff base-bearing vanillin motif. The structure of the product was confirmed via 1H and 13C-NMR spectroscopy and FT-IR spectroscopy. Due to the peculiar coordination nature and optical property of the synthesized compound, this work presents a promising colorimetric sensing molecular compound.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":"23 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135449410","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}
Edoardo Armano, A. Giraudo, Camillo Morano, M. Pallavicini, C. Bolchi
2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible to further synthetically useful conversions is the condensation of commercially available methyl 2,3-dibromopropionate with already suitably functionalized catechol. Here, we obtain methyl 8- and 5-nitro-1,4-benzodioxane-2-carboxylate by reaction of methyl 2,3-dibromopropionate with 3-nitrocatechol. After separation, the two positional isomers could be unequivocally identified by HMBC NMR analysis.
{"title":"Methyl 8- and 5-Nitro-1,4-Benzodioxane-2-Carboxylate","authors":"Edoardo Armano, A. Giraudo, Camillo Morano, M. Pallavicini, C. Bolchi","doi":"10.3390/m1661","DOIUrl":"https://doi.org/10.3390/m1661","url":null,"abstract":"2-Substituted 1,4-benzodioxanes bearing one or more substituents at benzene are important templates in the design and synthesis of a large variety of biologically active compounds. One of the most straightforward synthetic strategies to prepare them in racemic form and with a 2-substituent susceptible to further synthetically useful conversions is the condensation of commercially available methyl 2,3-dibromopropionate with already suitably functionalized catechol. Here, we obtain methyl 8- and 5-nitro-1,4-benzodioxane-2-carboxylate by reaction of methyl 2,3-dibromopropionate with 3-nitrocatechol. After separation, the two positional isomers could be unequivocally identified by HMBC NMR analysis.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47607832","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 six-coordinated indium(III) complex (APMe)(imSQMe)In(bipy) (1), bearing two types of redox-active ligands—mono- (imSQMe) and dianion (APMe) of 4,6-di-tert-butyl-N-(2,6-dimethylphenyl)-o-iminobenzoquinone and 2,2′-bipyridyl—was synthesized and characterized in detail. The intense, well-resolved ESR spectrum of 1 in dichloromethane solution clearly indicates the spin density delocalization between both AP and imSQ ligands. The UV-vis spectrum of 1 possesses an absorption band in the NIR region. The molecular structure of compound 1 was established by single-crystal X-ray diffraction analysis.
合成了一种六配位铟(III)配合物(APMe)(imSQMe)In(bipy)(1)，含4,6-二叔丁基- n -(2,6-二甲基苯基)-o-亚氨基苯醌和2,2 ' -联吡啶两种氧化还原活性配体-单(imSQMe)和双离子(APMe)。二氯甲烷溶液中1的强分辨ESR谱清楚地表明AP和imSQ配体之间的自旋密度离域。1的紫外-可见光谱在近红外区有一个吸收带。通过单晶x射线衍射分析确定了化合物1的分子结构。
{"title":"[4,6-Di-tert-butyl-N-(2,6-Dimethylphenyl)-o-Amidophenolato][4,6-Di-tert-butyl-N-(2,6-Dimethylphenyl)-o-Iminobenzosemiquinolato](2,2′-Bipyridyl)Indium(III)","authors":"I. Ershova, A. Cherkasov, A. Piskunov","doi":"10.3390/m1660","DOIUrl":"https://doi.org/10.3390/m1660","url":null,"abstract":"A six-coordinated indium(III) complex (APMe)(imSQMe)In(bipy) (1), bearing two types of redox-active ligands—mono- (imSQMe) and dianion (APMe) of 4,6-di-tert-butyl-N-(2,6-dimethylphenyl)-o-iminobenzoquinone and 2,2′-bipyridyl—was synthesized and characterized in detail. The intense, well-resolved ESR spectrum of 1 in dichloromethane solution clearly indicates the spin density delocalization between both AP and imSQ ligands. The UV-vis spectrum of 1 possesses an absorption band in the NIR region. The molecular structure of compound 1 was established by single-crystal X-ray diffraction analysis.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42686130","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}
Copper methoxide compound IPrCuOMe was unexpectedly formed in a reaction of IPrCuPPh2 with methyl acrylate. The alkoxide product was identified from the reaction mixture spectroscopically and structurally characterized. This C–O bond cleavage reaction likely depends on nucleophilicity of the Cu–P bond of IPrCuPPh2.
{"title":"Unexpected C–O Bond Cleavage by a Copper–Phosphido Compound","authors":"Steven G Dannenberg, R. Waterman","doi":"10.3390/m1659","DOIUrl":"https://doi.org/10.3390/m1659","url":null,"abstract":"Copper methoxide compound IPrCuOMe was unexpectedly formed in a reaction of IPrCuPPh2 with methyl acrylate. The alkoxide product was identified from the reaction mixture spectroscopically and structurally characterized. This C–O bond cleavage reaction likely depends on nucleophilicity of the Cu–P bond of IPrCuPPh2.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42640806","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}
Reaction of 3-aminobenzenesulfonic acid (HL1) with Cu(NO3)2·2.5H2O in H2O/DMF leads to the formation of the new bis(3-aminobenzenesulfonato-κN)-diaqua-bis(dimethylformamide-κO)-copper(II) complex [Cu(L1)2(DMF)2(H2O)2] (1) (HL1 = 3-aminobenzenesulfonic acid and DMF = N,N-dimethylformamide). Single crystal X-ray analysis reveals that the hexacoordinated copper(II) center adopts a distorted octahedral geometry with trans-oriented two 3-aminobenzenesulfonate ligands (L1−), two water and two dimethylformamide (DMF) molecules. Comparison of its crystal structure with that of the known bis(4-aminobenzenesulfonato-κN)diaquabis(dimethylformamide-κO)-copper(II) complex [Cu(L2)2(DMF)2(H2O)2] (2) (HL2 = 4-aminobenzenesulfonic acid) discloses that 1 and 2 are the isomers with an identical empirical formula (C18H30CuN4O10S2) and equal numbers of same coordinated solvents (DMF and water). H-bonded supramolecular structures and their corresponding topological analyses revealed a 2D with 6-connected hxl/Shubnikov plane net (3,6) for 1 and a 3D with 8-connected bcu; 8/4/c1; sqc3 net for 2, which are completely different.
{"title":"Bis(3-aminobenzenesulfonato-N)-diaqua-bis(N,N’-dimethylformamide-O)-copper(II)","authors":"S. Hazra, A. Karmakar","doi":"10.3390/m1658","DOIUrl":"https://doi.org/10.3390/m1658","url":null,"abstract":"Reaction of 3-aminobenzenesulfonic acid (HL1) with Cu(NO3)2·2.5H2O in H2O/DMF leads to the formation of the new bis(3-aminobenzenesulfonato-κN)-diaqua-bis(dimethylformamide-κO)-copper(II) complex [Cu(L1)2(DMF)2(H2O)2] (1) (HL1 = 3-aminobenzenesulfonic acid and DMF = N,N-dimethylformamide). Single crystal X-ray analysis reveals that the hexacoordinated copper(II) center adopts a distorted octahedral geometry with trans-oriented two 3-aminobenzenesulfonate ligands (L1−), two water and two dimethylformamide (DMF) molecules. Comparison of its crystal structure with that of the known bis(4-aminobenzenesulfonato-κN)diaquabis(dimethylformamide-κO)-copper(II) complex [Cu(L2)2(DMF)2(H2O)2] (2) (HL2 = 4-aminobenzenesulfonic acid) discloses that 1 and 2 are the isomers with an identical empirical formula (C18H30CuN4O10S2) and equal numbers of same coordinated solvents (DMF and water). H-bonded supramolecular structures and their corresponding topological analyses revealed a 2D with 6-connected hxl/Shubnikov plane net (3,6) for 1 and a 3D with 8-connected bcu; 8/4/c1; sqc3 net for 2, which are completely different.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45956424","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}
Bakr F. Abdel-Wahab, M. Bekheit, Benson M. Kariuki, Gamal A. El-Hiti
The reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and 2-acetylbenzofuran (2) in anhydrous ethanol containing a catalytic amount of concentrated hydrochloric acid under reflux for 2 h gave (E)-N’-(1-(benzofuran-2-yl)ethylidene)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (3) in 86% yield. The structure of the title heterocycle 3 was confirmed using nuclear magnetic resonance and X-ray diffraction.
{"title":"(E)-N’-(1-(Benzofuran-2-yl)ethylidene)-1-(4-Methoxyphenyl)-5-Methyl-1H-1,2,3-Triazole-4-Carbohydrazide","authors":"Bakr F. Abdel-Wahab, M. Bekheit, Benson M. Kariuki, Gamal A. El-Hiti","doi":"10.3390/m1657","DOIUrl":"https://doi.org/10.3390/m1657","url":null,"abstract":"The reaction of equimolar equivalents of 1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (1) and 2-acetylbenzofuran (2) in anhydrous ethanol containing a catalytic amount of concentrated hydrochloric acid under reflux for 2 h gave (E)-N’-(1-(benzofuran-2-yl)ethylidene)-1-(4-methoxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide (3) in 86% yield. The structure of the title heterocycle 3 was confirmed using nuclear magnetic resonance and X-ray diffraction.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" ","pages":""},"PeriodicalIF":0.6,"publicationDate":"2023-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44599196","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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