N. Li-Zhulanov, A. Rogachev, Yu. V. Gatilov, K. Volcho, N. Salakhutdinov
The reaction of (−)-nopol mesylate with piperazine in acetonitrile under reflux, afforded symmetric 1,4-bis(2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine in a good yield. The compound was fully characterized and its structure was confirmed using X-ray diffraction analysis.
在回流条件下，(-)-甲磺酸诺波尔酯与哌嗪在乙腈中发生反应，得到了对称的 1,4-双(2-((1R,5S)-6,6-二甲基双环[3.1.1]庚-2-烯-2-基)乙基)哌嗪，收率良好。利用 X 射线衍射分析对该化合物进行了全面表征并确认了其结构。
{"title":"1,4-Bis(2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine","authors":"N. Li-Zhulanov, A. Rogachev, Yu. V. Gatilov, K. Volcho, N. Salakhutdinov","doi":"10.3390/m1780","DOIUrl":"https://doi.org/10.3390/m1780","url":null,"abstract":"The reaction of (−)-nopol mesylate with piperazine in acetonitrile under reflux, afforded symmetric 1,4-bis(2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine in a good yield. The compound was fully characterized and its structure was confirmed using X-ray diffraction analysis.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"95 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140421868","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}
2-Methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid phenylamide was obtained as a single product in an experiment on the cyclization modes of a glycine-derived enamino amide. High yield and operational simplicity are the main features of the presented synthetic procedure. Additionally, this result extends our previous observations on the cyclization reactions of similarly functionalized enamines, by revealing the preferred cyclization pathway under Boc-deprotection conditions.
{"title":"2-Methyl-4-Oxo-4,5-Dihydro-1H-Pyrrole-3-Carboxylic Acid Phenylamide","authors":"P. Angelov, Pavel Yanev","doi":"10.3390/m1778","DOIUrl":"https://doi.org/10.3390/m1778","url":null,"abstract":"2-Methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid phenylamide was obtained as a single product in an experiment on the cyclization modes of a glycine-derived enamino amide. High yield and operational simplicity are the main features of the presented synthetic procedure. Additionally, this result extends our previous observations on the cyclization reactions of similarly functionalized enamines, by revealing the preferred cyclization pathway under Boc-deprotection conditions.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"24 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140421507","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}
Chadron M. Friesen, Nathan J. Weeks, Scott T. Iacono
The title compound was synthesized at a near-quantitative yield using the nucleophilic aromatic substitution of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with perfluoropyridine (PFP). The purity and structure were determined by NMR (1H, 13C, 19F), GC-EIMS, and single-crystal X-ray crystallography.
利用全氟吡啶（PFP）对 1,8-二氮杂双环[5.4.0]十一-7-烯（DBU）的亲核芳香取代作用，合成了标题化合物，产量接近定量。该化合物的纯度和结构是通过核磁共振（1H、13C、19F）、气相色谱-质谱和单晶 X 射线晶体学测定的。
{"title":"2,3,5,6-Tetrafluoro-[N-(3-aminopropyl)-ε-caprolactam]-4-pyridine","authors":"Chadron M. Friesen, Nathan J. Weeks, Scott T. Iacono","doi":"10.3390/m1777","DOIUrl":"https://doi.org/10.3390/m1777","url":null,"abstract":"The title compound was synthesized at a near-quantitative yield using the nucleophilic aromatic substitution of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with perfluoropyridine (PFP). The purity and structure were determined by NMR (1H, 13C, 19F), GC-EIMS, and single-crystal X-ray crystallography.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"14 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140438736","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}
K. A. Gomonov, V. V. Pelipko, Igor A. Litvinov, R. Baichurin, S. V. Makarenko
The synthesis of previously unknown 4,5-dimethylfuro[3,4-d]pyridazin-1(2H)-one has been proposed and structurally characterized via a single-crystal X-ray diffraction analysis, 1H, 13C–{1H}, 1H–13C HMQC, and 1H–13C HMBC NMR spectroscopy, and IR spectroscopy.
通过单晶 X 射线衍射分析、1H、13C-{1H}、1H-13C HMQC 和 1H-13C HMBC NMR 光谱以及红外光谱分析，提出了之前未知的 4,5-二甲基呋喃并[3,4-d]哒嗪-1(2H)-酮的合成方法和结构特征。
{"title":"4,5-Dimethylfuro[3,4-d]pyridazin-1(2H)-one","authors":"K. A. Gomonov, V. V. Pelipko, Igor A. Litvinov, R. Baichurin, S. V. Makarenko","doi":"10.3390/m1776","DOIUrl":"https://doi.org/10.3390/m1776","url":null,"abstract":"The synthesis of previously unknown 4,5-dimethylfuro[3,4-d]pyridazin-1(2H)-one has been proposed and structurally characterized via a single-crystal X-ray diffraction analysis, 1H, 13C–{1H}, 1H–13C HMQC, and 1H–13C HMBC NMR spectroscopy, and IR spectroscopy.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"327 ","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140448101","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}
Petr A. Buikin, A. Vologzhanina, Alexander A. Korlyukov
1-(3-(2-(Dimethylammonio)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate (sumatriptan succinate, HSum+·HSucc−) is a serotonin receptor agonist used to treat migraines. By the recrystallization of this substance from ethanol, its hemi(ethanol solvate), HSum+·HSucc−·0.5EtOH, was obtained. The solid was characterized by X-ray diffraction and FT-IR spectroscopy. In HSum+·HSucc−·0.5EtOH, solvent molecules link succinate anions into infinite O–H…O bonded chains, which are further connected by N–H…O interactions with cations into H-bonded layers.
1-(3-(2-(二甲基氨基)乙基)-1H-吲哚-5-基)-N-甲基甲磺酰胺琥珀酸盐（琥珀酸舒马曲普坦，HSum+-HSucc-）是一种血清素受体激动剂，用于治疗偏头痛。通过从乙醇中重结晶这种物质，得到了它的半乙醇溶物 HSum+-HSucc--0.5EtOH。通过 X 射线衍射和傅立叶变换红外光谱对这种固体进行了表征。在 HSum+-HSucc--0.5EtOH 中，溶剂分子将琥珀酸阴离子连接成无限的 O-H...O 键链，这些链通过 N-H...O 与阳离子的相互作用进一步连接成 H 键层。
{"title":"Sumatriptan Succinate Hemi(Ethanol Solvate)","authors":"Petr A. Buikin, A. Vologzhanina, Alexander A. Korlyukov","doi":"10.3390/m1766","DOIUrl":"https://doi.org/10.3390/m1766","url":null,"abstract":"1-(3-(2-(Dimethylammonio)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate (sumatriptan succinate, HSum+·HSucc−) is a serotonin receptor agonist used to treat migraines. By the recrystallization of this substance from ethanol, its hemi(ethanol solvate), HSum+·HSucc−·0.5EtOH, was obtained. The solid was characterized by X-ray diffraction and FT-IR spectroscopy. In HSum+·HSucc−·0.5EtOH, solvent molecules link succinate anions into infinite O–H…O bonded chains, which are further connected by N–H…O interactions with cations into H-bonded layers.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"45 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140494261","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}
Ildar R. Iusupov, V. Tafeenko, A. Altieri, A. Kurkin
This work describes the synthesis of spirocyclic compounds based on 8-azaspiro[5.6]dodec-10-ene. Diastereomerically pure pyrrole derivatives were prepared from the spirocyclic 1,2,3-triazole using a coupling reaction. The resulting compounds were characterized via 1H and 13C NMR spectroscopy and HRMS, and the crystallographic characteristics of one of them were studied via X-ray diffraction.
{"title":"Synthesis of Substituted Pyrrole Derivatives Based on 8-Azaspiro[5.6]dodec-10-ene Scaffold","authors":"Ildar R. Iusupov, V. Tafeenko, A. Altieri, A. Kurkin","doi":"10.3390/m1765","DOIUrl":"https://doi.org/10.3390/m1765","url":null,"abstract":"This work describes the synthesis of spirocyclic compounds based on 8-azaspiro[5.6]dodec-10-ene. Diastereomerically pure pyrrole derivatives were prepared from the spirocyclic 1,2,3-triazole using a coupling reaction. The resulting compounds were characterized via 1H and 13C NMR spectroscopy and HRMS, and the crystallographic characteristics of one of them were studied via X-ray diffraction.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"32 23","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139598206","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}
Tatiana S. Vlasova, Yulia E. Romanova, Ilya V. Taidakov, Stanislav A. Paveliev
In this work, the title compound was synthesized via the reaction of an aryl-substituted pyrazole with potassium tetrachloroplatinate, followed by the reaction of the postulated intermediate chloro-bridged dimer with a pyrazole-containing 1,3-diketonate ligand. The structure of the synthesized complex was established by 1H, 13C NMR spectroscopy and mass spectrometry. According to UV-Vis spectrometry studies, the obtained complex exhibits green fluorescence with a maximum at 514 nm. Based on cyclic voltammetry studies, the HOMO, LUMO and band gap values were calculated.
{"title":"(2-[4-Methylpyrazol-1-yl]phenyl)platinum(II) (1,3-bis[1-methyl-1H-pyrazol-4-yl]propane-1,3-dione)","authors":"Tatiana S. Vlasova, Yulia E. Romanova, Ilya V. Taidakov, Stanislav A. Paveliev","doi":"10.3390/m1764","DOIUrl":"https://doi.org/10.3390/m1764","url":null,"abstract":"In this work, the title compound was synthesized via the reaction of an aryl-substituted pyrazole with potassium tetrachloroplatinate, followed by the reaction of the postulated intermediate chloro-bridged dimer with a pyrazole-containing 1,3-diketonate ligand. The structure of the synthesized complex was established by 1H, 13C NMR spectroscopy and mass spectrometry. According to UV-Vis spectrometry studies, the obtained complex exhibits green fluorescence with a maximum at 514 nm. Based on cyclic voltammetry studies, the HOMO, LUMO and band gap values were calculated.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"34 12","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139599501","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}
R. Rusew, Kostadin Iliev, V. Kurteva, B. Shivachev
The title compound 1-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl) quinolin-1-ium bromide was obtained in good yield by a facile one-pot, one-step synthetic procedure involving quinoline and an aromatic α-bromo ketone. The product was isolated using hot recrystallization from acetone/acetonitrile solution and characterized using powder and single-crystal XRD, 1D and 2D NMR, DSC, FT-IR, and HRMS analyses.
{"title":"1-(2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl) Quinolin-1-ium Bromide","authors":"R. Rusew, Kostadin Iliev, V. Kurteva, B. Shivachev","doi":"10.3390/m1763","DOIUrl":"https://doi.org/10.3390/m1763","url":null,"abstract":"The title compound 1-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl) quinolin-1-ium bromide was obtained in good yield by a facile one-pot, one-step synthetic procedure involving quinoline and an aromatic α-bromo ketone. The product was isolated using hot recrystallization from acetone/acetonitrile solution and characterized using powder and single-crystal XRD, 1D and 2D NMR, DSC, FT-IR, and HRMS analyses.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"10 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139601234","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}
Cosimo Antonini, Franca M. Cordero, Fabrizio Machetti
We describe here the palladium hydrogenation of ethyl 5-(benzoyloxymethyl)isoxazole-3-carboxylate. The presence of two reducible sites in the molecule, namely the benzylic-like position and the isoxazole N–O bond, creates a possible competition. The results show that under the applied conditions, ethyl (Z)-2-amino-4-oxo-2-pentanoate is obtained as the only product. Accordingly, a domino process occurs, consisting of deoxygenation to the 5-methylisoxazole derivative followed by reductive opening of the isoxazole ring. The isoxazole substrate was prepared by NaOH-catalyzed cycloaddition-condensation of ethyl nitroacetate and propargyl benzoate in water. Complete characterizations of the isoxazole and Z-enaminone derivatives are reported.
{"title":"5-(Benzoyloxymethyl)isoxazole-3-carboxylic Acid Ethyl Ester","authors":"Cosimo Antonini, Franca M. Cordero, Fabrizio Machetti","doi":"10.3390/m1762","DOIUrl":"https://doi.org/10.3390/m1762","url":null,"abstract":"We describe here the palladium hydrogenation of ethyl 5-(benzoyloxymethyl)isoxazole-3-carboxylate. The presence of two reducible sites in the molecule, namely the benzylic-like position and the isoxazole N–O bond, creates a possible competition. The results show that under the applied conditions, ethyl (Z)-2-amino-4-oxo-2-pentanoate is obtained as the only product. Accordingly, a domino process occurs, consisting of deoxygenation to the 5-methylisoxazole derivative followed by reductive opening of the isoxazole ring. The isoxazole substrate was prepared by NaOH-catalyzed cycloaddition-condensation of ethyl nitroacetate and propargyl benzoate in water. Complete characterizations of the isoxazole and Z-enaminone derivatives are reported.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"37 23","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139528326","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}
Stille coupling between 5,5′-dibromo-4,4′-diphenyl-2,2′-bithiazole and 9-(2-ethylhexyl)-3-(tributylstannyl)-9H-carbazole in the presence of Pd(Ph3P)2Cl2 in toluene, heated at reflux for 2 h, gave 5,5′-bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole in 85% yield.
{"title":"5,5′-Bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole","authors":"Andreas S. Kalogirou, P. A. Koutentis","doi":"10.3390/m1761","DOIUrl":"https://doi.org/10.3390/m1761","url":null,"abstract":"Stille coupling between 5,5′-dibromo-4,4′-diphenyl-2,2′-bithiazole and 9-(2-ethylhexyl)-3-(tributylstannyl)-9H-carbazole in the presence of Pd(Ph3P)2Cl2 in toluene, heated at reflux for 2 h, gave 5,5′-bis[9-(2-ethylhexyl)-9H-carbazol-3-yl]-4,4′-diphenyl-2,2′-bithiazole in 85% yield.","PeriodicalId":509184,"journal":{"name":"Molbank","volume":"32 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139533420","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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