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Molbank, Volume 2018, Issue 1 (March 2018) – 17 articles

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6 pages, 4383 KiB  
Short Note
Cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine
by Alessandra Casnati, Elena Motti and Nicola Della Ca’
Molbank 2018, 2018(1), M988; https://doi.org/10.3390/M988 - 12 Mar 2018
Cited by 2 | Viewed by 2952
Abstract
The title compound—cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine—was synthesized in 83% isolated yield by a palladium-catalyzed one-pot strategy from 1-iodo-2-isopropoxybenzene and ortho-bromoaniline. The azepine derivative was fully characterized (FT-IR, MS, 1H and 13C-NMR, elemental analysis) [...] Read more.
The title compound—cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine—was synthesized in 83% isolated yield by a palladium-catalyzed one-pot strategy from 1-iodo-2-isopropoxybenzene and ortho-bromoaniline. The azepine derivative was fully characterized (FT-IR, MS, 1H and 13C-NMR, elemental analysis) and all proton and carbon signals have been completely assigned by 2D NMR experiments. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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5 pages, 567 KiB  
Short Note
5,5′-Bis[5-(9-decyl-9H-carbazol-3-yl)thien-2-yl]-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2018, 2018(1), M987; https://doi.org/10.3390/M987 - 8 Mar 2018
Cited by 2 | Viewed by 2832
Abstract
Stille coupling of 5,5′-dichloro-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione (8) with 9-decyl-3-[5-(tributylstannyl)thien-2-yl]-9H-carbazole and Pd(Ph3P)2Cl2 in PhMe, at ca. 110 °C, for 2 h, gave 5,5′-bis[5-(9-decyl-9H-carbazol-3-yl)thien-2-yl]-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione (7) in 51% yield. The latter is investigated as an oligomer donor for organic photovoltaics. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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4 pages, 350 KiB  
Short Note
1,3-Bis{[(E)-(9-ethyl-9H-carbazol-3-yl)methylene]amino}propan-2-ol
by Ismail Warad, Nisreen Amer, Huda Abedalrazeq, Anas Al Ali, Nabil Al-Zaqri, Hicham Elmsellem and Abdelkader Zarrouk
Molbank 2018, 2018(1), M986; https://doi.org/10.3390/M986 - 7 Mar 2018
Cited by 1 | Viewed by 3619
Abstract
Condensation of 1,3-diaminopropan-2-ol with 9-ethyl-9H-carbazole-3-carbaldehyde in absolute ethanol under stirring condition resulted in the formation of 1,3-bis{[(E)-(9-ethyl-9H-carbazol-3-yl)methylidene]amino}propan-2-ol within 0.5 in an excellent yield. The structure of the desired Schiff base was physically analyzed via CHN-elemental analysis, TOF-MS, [...] Read more.
Condensation of 1,3-diaminopropan-2-ol with 9-ethyl-9H-carbazole-3-carbaldehyde in absolute ethanol under stirring condition resulted in the formation of 1,3-bis{[(E)-(9-ethyl-9H-carbazol-3-yl)methylidene]amino}propan-2-ol within 0.5 in an excellent yield. The structure of the desired Schiff base was physically analyzed via CHN-elemental analysis, TOF-MS, UV-vis, FT-IR, and 1H & 13C-NMR. Computational studies of the structure were performed at the DFT/B3LYP/6-311++G(d) level of theory. Molecular electrostatic potential (MEP), Mulliken charge, IR-B3LYP, and structure optimization were performed. Full article
(This article belongs to the Special Issue Heterocycles)
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9 pages, 1858 KiB  
Communication
Gold-Catalyzed Synthesis of 2-Sulfenylspiroindolenines via Spirocyclizations
by Valentin Magné, Pascal Retailleau, Angela Marinetti, Arnaud Voituriez and Xavier Guinchard
Molbank 2018, 2018(1), M985; https://doi.org/10.3390/M985 - 23 Feb 2018
Cited by 8 | Viewed by 3446
Abstract
2-Phenylsulfenyl-N-propargyl tryptamines have been prepared by electrophilic sulfuration of the corresponding tryptamines. These compounds undergo gold-catalyzed spirocyclizations to the corresponding 2-phenylthiospiroindolenines in good yields. The compounds were analyzed by NMR experiments, infrared, mass spectra and X-ray diffraction. This method provides a [...] Read more.
2-Phenylsulfenyl-N-propargyl tryptamines have been prepared by electrophilic sulfuration of the corresponding tryptamines. These compounds undergo gold-catalyzed spirocyclizations to the corresponding 2-phenylthiospiroindolenines in good yields. The compounds were analyzed by NMR experiments, infrared, mass spectra and X-ray diffraction. This method provides a new efficient entry to the synthesis of 2-sulfenyl spiroindolic compounds. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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4 pages, 1452 KiB  
Short Note
1-Fluoro-2,5-dimethoxy-4-nitrobenzene
by Martin Sweeney, Patrick McArdle and Fawaz Aldabbagh
Molbank 2018, 2018(1), M984; https://doi.org/10.3390/M984 - 20 Feb 2018
Viewed by 4655
Abstract
1-Fluoro-2,5-dimethoxy-4-nitrobenzene was synthesized in 90% yield by the reaction of commercial 2-fluoro-1,4-dimethoxybenzene with nitric acid. The structure was confirmed by X-ray crystallography. The new title compound was characterized by 1H and 13C-NMR, elemental analysis, EI-MS and FT-IR. Full article
(This article belongs to the Section Structure Determination)
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3 pages, 551 KiB  
Short Note
Dimethyl 2,2′-[Carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate]
by Raffaella Mancuso, Katia F. Gioia, Antonio Palumbo Piccionello, Nicola Della Ca’, Carla Carfagna and Bartolo Gabriele
Molbank 2018, 2018(1), M983; https://doi.org/10.3390/M983 - 19 Feb 2018
Cited by 1 | Viewed by 2888
Abstract
The thus-far unknown ureic derivative dimethyl 2,2′-[carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate] has been efficiently synthesized by enantiospecific oxidative carbonylation of readily available l-tyrosine methyl ester, using a very simple catalytic system (PdI2 in conjunction with KI) under relatively mild conditions (100 °C [...] Read more.
The thus-far unknown ureic derivative dimethyl 2,2′-[carbonylbis(azanediyl)](2S,2′S)-bis[3-(4-hydroxyphenyl)propanoate] has been efficiently synthesized by enantiospecific oxidative carbonylation of readily available l-tyrosine methyl ester, using a very simple catalytic system (PdI2 in conjunction with KI) under relatively mild conditions (100 °C for 5 h in DME as the solvent and under 20 atm of a 4:1 mixture CO-air). Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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3 pages, 359 KiB  
Short Note
4,7-Dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide
by Timofey Chmovzh, Ekaterina Knyazeva, Vadim Popov and Oleg Rakitin
Molbank 2018, 2018(1), M982; https://doi.org/10.3390/M982 - 18 Feb 2018
Cited by 4 | Viewed by 3416
Abstract
Dihalogenated derivatives of [1,2,5]chalcogenadiazolo[3,4-d]pyridazines are of interest as precursors for both photovoltaic materials and biologically active compounds. In this communication, 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide was prepared via the reaction of 3,6-dichloro-5-nitropyridazin-4-amine with oxidizing agents; the best yield of the target compound [...] Read more.
Dihalogenated derivatives of [1,2,5]chalcogenadiazolo[3,4-d]pyridazines are of interest as precursors for both photovoltaic materials and biologically active compounds. In this communication, 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide was prepared via the reaction of 3,6-dichloro-5-nitropyridazin-4-amine with oxidizing agents; the best yield of the target compound was achieved in the reaction with (diacetoxyiodo)benzene in benzene by heating at reflux for two hours. The structure of the newly synthesized compound was established by means of 13C-NMR and IR spectroscopy, mass-spectrometry and elemental analysis. Full article
(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)
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Scheme 1

9 pages, 798 KiB  
Communication
A Novel Disulfide-Containing Polycationic Amphiphile: 1,28-Di[(cholest-5-en-3β-yl)disulfanyl]-4,25-dioxo-3,8,12,17,21,26-hexaazaoctacosane Tetrahydrochloride
by Pavel A. Puchkov, Elena V. Shmendel, Valeria D. Andreeva, Nina G. Morozova, Marina A. Zenkova and Mikhail A. Maslov
Molbank 2018, 2018(1), M981; https://doi.org/10.3390/M981 - 18 Feb 2018
Cited by 4 | Viewed by 3739
Abstract
The absence of highly effective delivery systems is a major challenge for gene therapy. Our work was aimed at the development of novel cationic liposomes possessing high transfection efficiency. For this purpose, a novel disulfide polycationic amphiphile 2S4 was synthesized. Cationic liposomes based [...] Read more.
The absence of highly effective delivery systems is a major challenge for gene therapy. Our work was aimed at the development of novel cationic liposomes possessing high transfection efficiency. For this purpose, a novel disulfide polycationic amphiphile 2S4 was synthesized. Cationic liposomes based on 2S4 and a helper lipid DOPE were formed by the thin film hydration method and exhibited effective plasmid DNA delivery into the HEK293 cells, with a transfection activity superior to that of the commercial agent Lipofectamine® 2000. Our results suggest that the polycationic amphiphile 2S4 is a promising candidate for in vitro nucleic acid delivery. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 703 KiB  
Communication
N-Vinylation of Imidazole and Benzimidazole with a Paramagnetic Vinyl Bromide
by Györgyi Úr, Gergely Gulyás Fekete, Kálmán Hideg and Tamás Kálai
Molbank 2018, 2018(1), M980; https://doi.org/10.3390/M980 - 1 Feb 2018
Cited by 1 | Viewed by 3555
Abstract
An N-vinylation of imidazole and benzimidazole with a paramagnetic vinyl bromide was investigated. Among the tested procedures, Pd-catalyzed reaction was the most powerful one. The N-vinylation of 2-aminobenzimidazole with a β-bromo-α,β-unsaturated pyrroline nitroxide aldehyde offered 1,1,3,3-tetramethyl-1H-benzimidazo[1,2-a]pyrrolo[3,4-e [...] Read more.
An N-vinylation of imidazole and benzimidazole with a paramagnetic vinyl bromide was investigated. Among the tested procedures, Pd-catalyzed reaction was the most powerful one. The N-vinylation of 2-aminobenzimidazole with a β-bromo-α,β-unsaturated pyrroline nitroxide aldehyde offered 1,1,3,3-tetramethyl-1H-benzimidazo[1,2-a]pyrrolo[3,4-e]pyrimidin-2(3H)-yloxyl radical and the corresponding non-cyclized Schiff base. The reaction of a β-bromo-α,β-unsaturated pyrroline nitroxide aldehyde with imidazole gave β-imidazo-α,β-unsaturated pyrroline nitroxide aldehyde, which was reduced to the alcohol and converted to an unstable allyl chloride. Full article
(This article belongs to the Special Issue Heterocycles)
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7 pages, 2042 KiB  
Communication
N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imid-azol-2-yl)benzeneamine
by Monika Dziełak, Damian Trzybiński, Jolanta Czerwińska, Bartosz Majchrzak, Barbara Tudek, Krzysztof Woźniak and Adam Mieczkowski
Molbank 2018, 2018(1), M979; https://doi.org/10.3390/M979 - 30 Jan 2018
Cited by 1 | Viewed by 3553
Abstract
N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)benzeneamine was obtained by condensation of N-(4-bromobenzyl)-3,1-benzoxazine-2,4-dione (N-(4-bromobenzyl)isatoic anhydride) with 4,5-dimethyl-1,2-phenylenediamine in refluxing acetic acid. This is a rare example of condensation of N-substituted 3,1-benzoxazine-2,4-dione with 1,2-phenylenediamine, which resulted in the formation of a [...] Read more.
N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)benzeneamine was obtained by condensation of N-(4-bromobenzyl)-3,1-benzoxazine-2,4-dione (N-(4-bromobenzyl)isatoic anhydride) with 4,5-dimethyl-1,2-phenylenediamine in refluxing acetic acid. This is a rare example of condensation of N-substituted 3,1-benzoxazine-2,4-dione with 1,2-phenylenediamine, which resulted in the formation of a benzimidazole derivative with a moderate yield. Crystallographic studies and initial biological screening were performed for the obtained product. Full article
(This article belongs to the Special Issue Heterocycles)
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5 pages, 650 KiB  
Short Note
5-Methyl-3,8-di-(2-amino-4-bromophenyl)-4,9-dioxa-1,2,6,7-tetraaza-5λ5-phosphaspiro[4.4]nona-2,7-diene
by Sławomir Kasperowicz, Jolanta Czerwińska, Bartosz Majchrzak, Barbara Tudek and Adam Mieczkowski
Molbank 2018, 2018(1), M978; https://doi.org/10.3390/M978 - 30 Jan 2018
Viewed by 3156
Abstract
5-Methyl-3,8-di-(2-amino-4-bromophenyl)-4,9-dioxa-1,2,6,7-tetraaza-5λ5-phosphaspiro[4.4]nona-2,7-diene was obtained by condensation of 2-amino-5-bromobenzohydrazide and methylphosphonyl dichloride in the presence of triethylamine. An initial biological screening was performed for the resulting product. The synthesized compound showed relatively strong cytotoxic activity, which was, however, similar for cancer and non-cancer [...] Read more.
5-Methyl-3,8-di-(2-amino-4-bromophenyl)-4,9-dioxa-1,2,6,7-tetraaza-5λ5-phosphaspiro[4.4]nona-2,7-diene was obtained by condensation of 2-amino-5-bromobenzohydrazide and methylphosphonyl dichloride in the presence of triethylamine. An initial biological screening was performed for the resulting product. The synthesized compound showed relatively strong cytotoxic activity, which was, however, similar for cancer and non-cancer cell lines. Full article
(This article belongs to the Special Issue Heterocycles)
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6 pages, 1341 KiB  
Communication
Straightforward Synthesis of N-Methyl-4-(pin)B-2(3H)-benzothiazol-2-one: A Promising Cross-Coupling Reagent
by Shotaro Izawa, Hidefumi Nakatsuji and Yoo Tanabe
Molbank 2018, 2018(1), M976; https://doi.org/10.3390/M976 - 23 Jan 2018
Cited by 2 | Viewed by 3838
Abstract
Cyclo-condensation of N-methyl-2-bromoaniline with chlorocarbonylsulfenyl chloride (CCSC) promoted by PhNMe2 and AlCl3, afforded N-methyl-2-bromo-2(3H)-benzothiazol-2-one in good yield. Miyaura–Ishiyama cross-coupling of this brominated 2(3H)-benzothiazol-2-one with bis(pinacolato)diborone [(pin)2B2] produced a novel N [...] Read more.
Cyclo-condensation of N-methyl-2-bromoaniline with chlorocarbonylsulfenyl chloride (CCSC) promoted by PhNMe2 and AlCl3, afforded N-methyl-2-bromo-2(3H)-benzothiazol-2-one in good yield. Miyaura–Ishiyama cross-coupling of this brominated 2(3H)-benzothiazol-2-one with bis(pinacolato)diborone [(pin)2B2] produced a novel N-methyl-4-(pin)B-2(3H)-benzothiazol-2-one (3) using (pin)2B2 in the presence of the PdCl2(PPh3)2 catalyst. The obtained 4-(pin)B compound is regarded as a new entry for the library of Suzuki–Miyaura cross-coupling reactions. Full article
(This article belongs to the Special Issue Heterocycles)
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5 pages, 1305 KiB  
Short Note
5-Amino-3-methyl-1,2,4-thiadiazole
by R. Alan Aitken and Alexandra M. Z. Slawin
Molbank 2018, 2018(1), M977; https://doi.org/10.3390/M977 - 21 Jan 2018
Cited by 1 | Viewed by 4624
Abstract
An improved procedure for isolation of 5-amino-3-methyl-1,2,4-thiadiazole in pure form on a multi-gram scale without chromatography is reported. Its 1H and 13C-NMR and IR data are presented and previously published erroneous data corrected. The molecular structure is confirmed by X-ray diffraction [...] Read more.
An improved procedure for isolation of 5-amino-3-methyl-1,2,4-thiadiazole in pure form on a multi-gram scale without chromatography is reported. Its 1H and 13C-NMR and IR data are presented and previously published erroneous data corrected. The molecular structure is confirmed by X-ray diffraction which shows layers consisting of an elaborate two-dimensional hydrogen bonded network of molecules. Full article
(This article belongs to the Special Issue Heterocycles)
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5 pages, 324 KiB  
Short Note
N-(3-Chloro-2-methylphenyl)-4-(4-fluorophenyl)-1,3-thiazol-2-amine
by Nadine Uwabagira, Balladka Kunhana Sarojini and Boja Poojary
Molbank 2018, 2018(1), M975; https://doi.org/10.3390/M975 - 19 Jan 2018
Cited by 2 | Viewed by 3254
Abstract
The two precursors 3-chloro-2-methylphenylthiourea 2 and 4-fluorophenacyl bromide 4 are reacted under Hantzsch thiazole synthesis condition to yield the new compound N-(3-chloro-2-methylphenyl)-4-(4-fluorophenyl)-1,3-thiazol-2-amine 5. The IR, 1H-NMR, 13C-NMR and mass spectral data are presented, along with its in vitro antibacterial [...] Read more.
The two precursors 3-chloro-2-methylphenylthiourea 2 and 4-fluorophenacyl bromide 4 are reacted under Hantzsch thiazole synthesis condition to yield the new compound N-(3-chloro-2-methylphenyl)-4-(4-fluorophenyl)-1,3-thiazol-2-amine 5. The IR, 1H-NMR, 13C-NMR and mass spectral data are presented, along with its in vitro antibacterial activity against Staphylococcus aureus and Chromobacterium violaceum. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 378 KiB  
Communication
3-[2-(Oxiran-2-yl)ethyl]-1-{4-[(2-oxiran-2-yl)ethoxy]benzyl}imidazolium bis(Trifluoromethane)sulfonimide
by Charline Chardin, Jacques Rouden, Sébastien Livi and Jérôme Baudoux
Molbank 2018, 2018(1), M974; https://doi.org/10.3390/M974 - 13 Jan 2018
Cited by 7 | Viewed by 3825
Abstract
The synthesis of 3-[2-(oxiran-2-yl)ethyl]-1-{4-[(2-oxiran-2-yl)ethoxy]benzyl}imidazolium bis(trifluoromethane)sulfonimide was achieved in seven steps with an overall yield of 63%. This ionic liquid monomer is based on an imidazolium core containing a phenoxy moiety and aliphatic chains with a reactive epoxide at both ends. This imidazolium was [...] Read more.
The synthesis of 3-[2-(oxiran-2-yl)ethyl]-1-{4-[(2-oxiran-2-yl)ethoxy]benzyl}imidazolium bis(trifluoromethane)sulfonimide was achieved in seven steps with an overall yield of 63%. This ionic liquid monomer is based on an imidazolium core containing a phenoxy moiety and aliphatic chains with a reactive epoxide at both ends. This imidazolium was obtained by an efficient, reproducible, and scalable synthesis from inexpensive reagents. In the last step, a powerful oxidative agent was successfully used to generate two epoxy functions with only acetone as a byproduct. The monomer structure and intermediates were analyzed by NMR experiments, infrared, and mass spectra. In addition, the thermal properties of the diepoxide were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Full article
(This article belongs to the Special Issue Heterocycles)
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6 pages, 689 KiB  
Communication
Synthesis of All Stereoisomers of 1-(4-Methoxyphenyl)-2,3,4,9-tetrahydro-N-methyl-1H-pyrido[3,4-b]indole-3-carboxamide
by Momoko Onda, Ayaka Higashida, Takako Hirano, Toshiyuki Nishio and Wataru Hakamata
Molbank 2018, 2018(1), M973; https://doi.org/10.3390/M973 - 10 Jan 2018
Viewed by 3046
Abstract
In this study, all four stereoisomers of tryptoline or tetrahydro-β-carboline were synthesized in high yields by the catalyst-free amidation of methyl ester using methylamine under mild conditions. All isomers of the obtained amide and the precursor methyl ester were subjected to cell viability [...] Read more.
In this study, all four stereoisomers of tryptoline or tetrahydro-β-carboline were synthesized in high yields by the catalyst-free amidation of methyl ester using methylamine under mild conditions. All isomers of the obtained amide and the precursor methyl ester were subjected to cell viability measurements on HeLa cells. The results indicated that the stereochemistry of the derivatives is clearly related to cell viability. Full article
(This article belongs to the Section Organic Synthesis)
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2 pages, 279 KiB  
Editorial
Acknowledgement to Reviewers of Molbank in 2017
by Molbank Editorial Office
Molbank 2018, 2018(1), M972; https://doi.org/10.3390/M972 - 9 Jan 2018
Viewed by 1895
Abstract
Peer review is an essential part in the publication process, ensuring that Molbank maintains high quality standards for its published papers. In 2017, a total of 46 papers were published in the journal.[...] Full article
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