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8 pages, 996 KiB  
Short Note
4,4’-(Thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(1-methyl-1-pyridinium) Iodide
by Lorenza Romagnoli, Alessandro Latini and Andrea D’Annibale
Molbank 2024, 2024(2), M1817; https://doi.org/10.3390/M1817 (registering DOI) - 06 May 2024
Viewed by 141
Abstract
In the vast field of organic functional materials, viologens are widely recognized as an extremely versatile family of substances, due in part to the possibility of extending conjugation between the terminal pyridinium rings, for instance through the insertion of additional aromatic moieties. In [...] Read more.
In the vast field of organic functional materials, viologens are widely recognized as an extremely versatile family of substances, due in part to the possibility of extending conjugation between the terminal pyridinium rings, for instance through the insertion of additional aromatic moieties. In this work, a new, extended viologen with a thiophene core and two acetylene bonds is presented. It was synthesized through a straightforward route, using well-established Sonogashira coupling reactions, and its optical properties were investigated by UV–visible absorption and fluorescence spectroscopy, revealing a very interesting material for diverse fluorescence-related applications. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 860 KiB  
Short Note
Di-µ-(1-(3-(1H-imidazol-1-yl)propyl)-2-methyl-4-oxo-1,4-dihydropyridin-3-olate)-bis[(η5-pentamethylcyclopentadienyl)iridium(III)] Chloride
by Ilya A. Shutkov, Nikolai A. Melnichuk, Konstantin A. Lyssenko, Nataliya E. Borisova, Olga N. Kovaleva and Alexey A. Nazarov
Molbank 2024, 2024(2), M1816; https://doi.org/10.3390/M1816 (registering DOI) - 05 May 2024
Viewed by 363
Abstract
A metallacyclic maltol-tethered organometallic Ir(III) half-sandwich complex was synthesized as an analog of the ruthenium anticancer complexes (RAPTA/RAED) to evaluate its in vitro antiproliferative activity against various human cancer cell lines. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 1019 KiB  
Communication
Synthesis and Spectroscopic Study of New 1H-1-Alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4]triazoles
by Ion Burcă, Valentin Badea, Vasile-Nicolae Bercean and Francisc Péter
Molbank 2024, 2024(2), M1815; https://doi.org/10.3390/M1815 - 24 Apr 2024
Viewed by 266
Abstract
The nitrosation of 1H-1-alkyl-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazoles leads to new 1H-1-alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4] triazoles that react in acidic media, giving rise to 1H-1-alkyl-7-hydroxyimino-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazolium salts. These compounds were characterized by FT-IR, UV-Vis, 1H-NMR, 13C-NMR, and 15N-NMR spectroscopic techniques. Full article
(This article belongs to the Collection Heterocycle Reactions)
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6 pages, 1469 KiB  
Short Note
5,6-Diphenyl-1,3,4,7-tetra-p-tolyl-1,3,3a,7a-tetrahydropentaleno[1,2-c]furan
by Shu-Kai Chen, Yi-Hung Liu and Shiuh-Tzung Liu
Molbank 2024, 2024(2), M1814; https://doi.org/10.3390/M1814 - 24 Apr 2024
Viewed by 259
Abstract
The reaction of (Z)-5-phenyl-1,3-di-p-tolylpent-2-en-4-yn-1-ol (1) with trimethylsilyl chloride in dichloromethane at ambient temperature gave a dimeric ether compound 2 in 30% yield. Subsequently, heating 2 in toluene under refluxing temperature rendered the title compound quantitatively. The structure [...] Read more.
The reaction of (Z)-5-phenyl-1,3-di-p-tolylpent-2-en-4-yn-1-ol (1) with trimethylsilyl chloride in dichloromethane at ambient temperature gave a dimeric ether compound 2 in 30% yield. Subsequently, heating 2 in toluene under refluxing temperature rendered the title compound quantitatively. The structure of this tricyclic-fused compound was characterized using NMR, mass spectroscopy, and X-ray crystallography. This unique linear tricyclic fused furan framework is reported for the first time. Full article
(This article belongs to the Section Organic Synthesis)
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5 pages, 946 KiB  
Short Note
5,5′-Thiobis(3-bromoisothiazole-4-carbonitrile)
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2024, 2024(2), M1813; https://doi.org/10.3390/M1813 - 24 Apr 2024
Viewed by 285
Abstract
The reaction of sodium 2,2-dicyanoethene-1,1-bis(thiolate) with bromine (2 equiv.) in CCl4 gave 3,5-dibromoisothiazole-3-carbonitrile and 5,5′-thiobis(3-bromoisothiazole-4-carbonitrile) in 7% and 18% yields, respectively. The latter novel compound was fully characterized. Full article
(This article belongs to the Section Organic Synthesis)
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8 pages, 1315 KiB  
Short Note
2S-(1RS-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine
by Angelica Artasensi and Laura Fumagalli
Molbank 2024, 2024(2), M1812; https://doi.org/10.3390/M1812 - 24 Apr 2024
Viewed by 357
Abstract
In medicinal chemistry, the precise configuration of molecules is a crucial determinant of their pharmacological properties. Hence, the introduction of a new chiral center during the synthetic pathway involves the assignment of configuration. Herein we assign, by means of molecular modeling 1H [...] Read more.
In medicinal chemistry, the precise configuration of molecules is a crucial determinant of their pharmacological properties. Hence, the introduction of a new chiral center during the synthetic pathway involves the assignment of configuration. Herein we assign, by means of molecular modeling 1H and 2D Nuclear Overhauser Effect NMR techniques, the configuration of the two diastereomers 2S-(1R-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine and 2S-(1S-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine, which are useful to synthetize analogs of the potent and highly selective dipeptidyl peptidase IV and carbonic anhydrase inhibitor recently published. Full article
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5 pages, 552 KiB  
Short Note
Chloro(η22-cycloocta-1,5-diene){1-benzyl-3-[(S)-2-hydroxy-1-methylethyl]benzimidazol-2-ylidene}rhodium(I)
by Satoshi Sakaguchi and Shogo Matsuo
Molbank 2024, 2024(2), M1811; https://doi.org/10.3390/M1811 - 19 Apr 2024
Viewed by 305
Abstract
Previously, we demonstrated the synthesis of a well-defined hydroxyalkyl-functionalized N-heterocyclic carbene (NHC)/Ru(II) complex through the transmetalation reaction between [RuCl2(p-cymene)]2 and the corresponding NHC/Ag(I) complex derived from a chiral benzimidazolium salt using the Ag2O method. In [...] Read more.
Previously, we demonstrated the synthesis of a well-defined hydroxyalkyl-functionalized N-heterocyclic carbene (NHC)/Ru(II) complex through the transmetalation reaction between [RuCl2(p-cymene)]2 and the corresponding NHC/Ag(I) complex derived from a chiral benzimidazolium salt using the Ag2O method. In this study, we successfully synthesized [RhX(cod)(NHC)] complexes through a one-pot deprotonation route. The hydroxyalkyl-substituted benzimidazolium salt reacted with [Rh(OH)(cod)]2 in THF at room temperature, affording the corresponding monodentate NHC/Rh(I) complex in nearly quantitative yield. The rhodium complex was characterized using NMR, HRMS measurement, and elemental analysis. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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5 pages, 640 KiB  
Short Note
Chloro(η22-cycloocta-1,5-diene){1-[(2-[(S)-1-(hydroxymethyl)-3-methylbutyl]amino)-2-oxoethyl]-3-(1-naphthalenylmethyl)benzimidazol-2-ylidene}rhodium(I)
by Satoshi Sakaguchi and Shogo Matsuo
Molbank 2024, 2024(2), M1810; https://doi.org/10.3390/M1810 - 19 Apr 2024
Viewed by 319
Abstract
Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]2 (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H [...] Read more.
Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]2 (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H bond of the azolium ring in the hydroxyamide-substituted benzimidazolium salt 1. This reaction between 1 and 2 proceeded in THF at room temperature without temperature control, affording the desired NHC/Rh complex 3 in excellent yield. The characterization of complex 3 was accomplished through NMR and HRMS analyses, revealing its existence as a diastereomeric mixture of two NHC/Rh complexes. Furthermore, its catalytic performance was briefly evaluated in the reaction between 2-naphthaldehyde (5) and phenylboronic acid (6). Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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4 pages, 656 KiB  
Short Note
1-(3-Chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea
by Daria Zapravdina and Vladimir Burmistrov
Molbank 2024, 2024(2), M1809; https://doi.org/10.3390/M1809 - 18 Apr 2024
Viewed by 346
Abstract
The compound 1-(3-chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea was synthesized for the first time from 6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexan-1-amine and 3-chlorophenylisothiocyanate in DMF with a 60% yield. It was characterized by 1H, 13C{1H} NMR, FT-IR, MS, and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis)
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7 pages, 1059 KiB  
Short Note
Diiodido-bis{N-[2-(diphenylphosphino)benzylidene]benzylamine-κ2N,P}dicopper(I)
by Julian Süß, Uwe Monkowius and Manfred Zabel
Molbank 2024, 2024(2), M1808; https://doi.org/10.3390/M1808 - 18 Apr 2024
Viewed by 372
Abstract
The one-pot template reaction between 2-(diphenylphosphino)benzaldehyde, benzylamine and copper(I) iodide yields the dinuclear copper complex (P∩N)2Cu2I2, as revealed by single-crystal X-ray diffraction. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1274 KiB  
Short Note
3,3’-(4,11-Bis(4-(trifluoromethyl)benzyl)-1,4,8,11-Tetraazacyclotetradecane-1,8-diyl)dipropanenitrile
by Inês M. Nunes, Elisabete R. Silva and Luis G. Alves
Molbank 2024, 2024(2), M1807; https://doi.org/10.3390/M1807 - 17 Apr 2024
Viewed by 391
Abstract
The cyclam derivative (NCCH2CH2)2(4-CF3PhCH2)2Cyclam was prepared by the reaction of H2(4-CF3PhCH2)2Cyclam with acrylonitrile in methanol. The compound was fully characterized by elemental analysis, [...] Read more.
The cyclam derivative (NCCH2CH2)2(4-CF3PhCH2)2Cyclam was prepared by the reaction of H2(4-CF3PhCH2)2Cyclam with acrylonitrile in methanol. The compound was fully characterized by elemental analysis, mass spectrometry as well as IR and NMR spectroscopy. Crystals of (NCCH2CH2)2(4-CF3PhCH2)2Cyclam suitable for single-crystal X-ray diffraction were obtained by the slow evaporation of a chloroform solution of the compound. The establishment of non-classical hydrogen bonds and unusual nitrile–nitrile and π(CN)π interactions determined the solid-state supramolecular architecture of (NCCH2CH2)2(4-CF3PhCH2)2Cyclam. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 954 KiB  
Communication
Synthesis and Analytical Characterization of Cyclization Products of 3-Propargyloxy-5-benzyloxy-benzoic Acid Methyl Ester
by Matteo Mori, Giulia Cazzaniga, Donatella Nava and Elena Pini
Molbank 2024, 2024(2), M1806; https://doi.org/10.3390/M1806 - 16 Apr 2024
Viewed by 389
Abstract
In the context of our ongoing studies on chromane derivatives as inhibitors of the salicylate synthase from M. tuberculosis, we isolated a new, unexpected compound from the cyclization of 3-(propargyloxy)-5-benzyloxy-benzoic acid methyl ester. Its molecular structure was elucidated by means of 1D [...] Read more.
In the context of our ongoing studies on chromane derivatives as inhibitors of the salicylate synthase from M. tuberculosis, we isolated a new, unexpected compound from the cyclization of 3-(propargyloxy)-5-benzyloxy-benzoic acid methyl ester. Its molecular structure was elucidated by means of 1D and 2D NMR analyses, FT-IR, ESI-MS, and HRMS. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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7 pages, 4214 KiB  
Communication
The Synthesis and Structure of Scandium Dichloride of Sterically Demanding Aminopyridinato Ligands
by Sadaf Qayyum
Molbank 2024, 2024(2), M1805; https://doi.org/10.3390/M1805 - 10 Apr 2024
Viewed by 525
Abstract
The reaction of the potassium salt of (2,6-diisopropylphenyl)-[6-(2,4,6-triisopropylphenyl)-pyridine-2-yl]-amine (Ap*H) with the equimolar ratio of [ScCl3] in tetrahydrofuran (thf) resulted in the mononuclear mono(aminopyridinato) scandium dichloride complex [Ap*ScCl2(thf)2]. An X-ray analysis showed the title compound to be monomeric. [...] Read more.
The reaction of the potassium salt of (2,6-diisopropylphenyl)-[6-(2,4,6-triisopropylphenyl)-pyridine-2-yl]-amine (Ap*H) with the equimolar ratio of [ScCl3] in tetrahydrofuran (thf) resulted in the mononuclear mono(aminopyridinato) scandium dichloride complex [Ap*ScCl2(thf)2]. An X-ray analysis showed the title compound to be monomeric. The compound [C40H59Cl2N2O2Sc] crystallized in the monoclinic space group, P21/n, and possessed the following cell parameters: a  =  12.4441(8) b  =  22.9975(10) c  =  13.9971(8) Å, β  =  92.297(5)°, V  =  4002.5(4) A3, and Z  =  4. Hirshfeld analyses show that H…H (91.1%), H…C/C…H (5.0%), and H…Cl/Cl…H (3.9%) are the contributing interactions in the solid-state structure. The compound was further characterized by NMR spectroscopy, and its purity was confirmed by elemental analysis. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 382 KiB  
Short Note
1,2-Dibenzoylthiosemicarbazide
by Burcă Ion, Badea Valentin, Todea Anamaria and Bercean Vasile-Nicolae
Molbank 2024, 2024(2), M1804; https://doi.org/10.3390/M1804 - 09 Apr 2024
Viewed by 395
Abstract
When 1-benzoylthiosemicarbazide (2) or thiosemicarbazide (1) were treated with benzoyl chloride in a basic medium, a mixture of two compounds was obtained: 1,2-dibenzoylthiosemicarbazide (3) and 1,4-dibenzoylthiosemicarbazide (4). To determine the structure of the novel compounds, [...] Read more.
When 1-benzoylthiosemicarbazide (2) or thiosemicarbazide (1) were treated with benzoyl chloride in a basic medium, a mixture of two compounds was obtained: 1,2-dibenzoylthiosemicarbazide (3) and 1,4-dibenzoylthiosemicarbazide (4). To determine the structure of the novel compounds, 2D NMR spectroscopy techniques such as 1H-13C and 1H-15N were employed. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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6 pages, 2425 KiB  
Short Note
Benzo[d][1,2,3]oxadithiole 2-Oxide
by R. Alan Aitken, David B. Cordes, Arun Goyal and Aidan P. McKay
Molbank 2024, 2024(2), M1803; https://doi.org/10.3390/M1803 - 07 Apr 2024
Viewed by 550
Abstract
A simplified synthesis of the title compound is reported and its 1H and 13C NMR data are fully assigned including determination of H–H and C–H coupling constants. Its X-ray structure has been determined for the first time. NMR data are also [...] Read more.
A simplified synthesis of the title compound is reported and its 1H and 13C NMR data are fully assigned including determination of H–H and C–H coupling constants. Its X-ray structure has been determined for the first time. NMR data are also presented for the oxygen analogue. Full article
(This article belongs to the Section Structure Determination)
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