Molbank

7 pages, 1544 KiB

Open AccessShort Note

N-(1-azido-2-(azidomethyl)butan-2-yl)-4-methylbenzenesulfonamide

by Sara Hajib, Younas Aouine, Hassane Faraj and Anouar Alami

Molbank 2022, 2022(3), M1448; https://doi.org/10.3390/M1448 - 19 Sep 2022

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A new bi-triazole precursor, N-(1-azido-2-(azidomethyl)butan-2-yl)-4-methylbenzenesulfonamide, was synthesized in two steps from 2-amino-2-ethyl-1,3-propanediol, with an overall yield of 80%. The chemical structures of the products obtained were established based on 1D and 2D NMR, IR spectroscopy, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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8 pages, 2921 KiB

Open AccessCommunication

Synthesis, Characterization, and Structure of Mixed-Ligand Cobalt (II) Complex with N, O Donor Sites

by Debdas Mandal, Anwesha Haldar, Priyanka Chakraborty and Rakesh Ganguly

Molbank 2022, 2022(3), M1447; https://doi.org/10.3390/M1447 - 16 Sep 2022

Cited by 2 | Viewed by 1870

Abstract

A mononuclear octahedral mixed-ligand cobalt (II) complex [Co(H₂L)(PhCOO)₂] (1) has been prepared by using H₂L (N,N′-dimethyl-N,N′-bi(2-hydroxy-3,5-di methyl benzyl)-ethylenediamine) as a facially coordinating tetradentate ligand with a N [...] Read more.

A mononuclear octahedral mixed-ligand cobalt (II) complex [Co(H₂L)(PhCOO)₂] (1) has been prepared by using H₂L (N,N′-dimethyl-N,N′-bi(2-hydroxy-3,5-di methyl benzyl)-ethylenediamine) as a facially coordinating tetradentate ligand with a N₂O₂ donor center along with sodium benzoate as an ancillary ligand. Complex 1 has been characterized by a single-crystal X-ray diffraction study, as well as by other spectroscopic tools. The complex crystallizes in the monoclinic space group C₂ with a = 31.73(3) Å, b = 7.868(3) Å, c = 19.131(15) Å, and β = 125.25(3)°. The single-crystal X-ray diffraction study shows that in the mononuclear cobalt (II) complex [Co(H₂L)(PhCOO)₂] (1), the metal center adopts an octahedral environment. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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5 pages, 903 KiB

Open AccessShort Note

Allobetulin

by Mirosława Grymel and Jakub Adamek

Molbank 2022, 2022(3), M1446; https://doi.org/10.3390/M1446 - 15 Sep 2022

Cited by 3 | Viewed by 1781

Abstract

Allobetulin was synthesized at room temperature, starting from betulin by Wagner–Meerwein rearrangement in the presence of tetrafluoroboric acid diethyl ether complex. The structure of the compound obtained was confirmed by spectroscopic methods (¹H, ¹³C NMR and IR). Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1948 KiB

Open AccessCommunication

X-ray Structures of 3-Acetyloxazolidin-2-one, 3-Acetyloxazolin-2-one and Oxazolin-2(3H)-one

by R. Alan Aitken, Joe S. Logan and Alexandra M. Z. Slawin

Molbank 2022, 2022(3), M1445; https://doi.org/10.3390/M1445 - 14 Sep 2022

Viewed by 1529

Abstract

The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one 1 and its unsaturated analogue 3-acetyloxazolin-2-one 3 show a planar imide nitrogen with the exocyclic C=O oriented anti to the ring N–C(=O) bond and [...] Read more.

The X-ray structures of three simple heterocyclic compounds have been obtained for the first time. Structures of both 3-acetyloxazolidin-2-one 1 and its unsaturated analogue 3-acetyloxazolin-2-one 3 show a planar imide nitrogen with the exocyclic C=O oriented anti to the ring N–C(=O) bond and negligible intermolecular interactions, a pattern consistent with previously reported analogues. In contrast the parent NH heterocycle, oxazolin-2(3H)-one 4, exists as hydrogen bonded dimers of two closely similar independent molecules but an unusual type of disorder involving exchange of the ring O and NH positions results in a very high R factor. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

6 pages, 661 KiB

Open AccessShort Note

Ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine)

by Roberto E. Blanco-Carapia, Enrique A. Aguilar-Rangel, Alejandro Islas-Jácome and Eduardo González-Zamora

Molbank 2022, 2022(3), M1444; https://doi.org/10.3390/M1444 - 13 Sep 2022

Cited by 1 | Viewed by 1630

Abstract

The new bis-heterocyclic compound ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine) (1) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a [...] Read more.

The new bis-heterocyclic compound ferrocenyl-bis-(1-(4-benzyl-5-morpholinooxazol-2-yl)-N-(4-(trifluoromethyl)benzyl)methanamine) (1) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a Lewis-acid catalyst, microwaves as a heat source, and toluene as a solvent. The synthesized compound was characterized by 1D (¹H, ¹³C, and ¹⁹F) and 2D (COSY, HSQC, and HMBC) NMR, HRMS, and FT-IR. Full article

(This article belongs to the Collection Heterocycle Reactions)

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8 pages, 2545 KiB

Open AccessShort Note

Tris(μ₂-carbonyl)octacarbonyl(triphenylphosphite)tetracobalt

by Isabelle Jourdain, Michael Knorr, Carsten Strohmann and Rebecca Scheel

Molbank 2022, 2022(3), M1443; https://doi.org/10.3390/M1443 - 10 Sep 2022

Viewed by 1824

Abstract

In toluene solution, the reaction of [Co₂(CO)₈] with an equimolar amount of [P(OPh)₃] yields first [Co₂(CO)₇{P(OPh)₃}] 1. Following heating of 1, an alternative synthetic access to the tetranuclear cluster [...] Read more.

In toluene solution, the reaction of [Co₂(CO)₈] with an equimolar amount of [P(OPh)₃] yields first [Co₂(CO)₇{P(OPh)₃}] 1. Following heating of 1, an alternative synthetic access to the tetranuclear cluster [{Co₄(μ₂-CO)₃(CO)₈{P(OPh)₃}] 2 is provided in a condensation reaction. Compound 2 has been characterized by IR and ³¹P NMR spectroscopy. The tetranuclear cluster framework has been ascertained by a single-crystal X-ray diffraction study performed at 100 K. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 675 KiB

Open AccessShort Note

3-(Phenylethynyl)-7H-benzo[de]anthracen-7-one

by Armands Maļeckis, Evans Griškjāns, Marija Cvetinska and Elena Kirilova

Molbank 2022, 2022(3), M1442; https://doi.org/10.3390/M1442 - 8 Sep 2022

Cited by 2 | Viewed by 1921

Abstract

The present work describes the facile synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one via a Sonogashira coupling reaction. The structure of the synthesized benzanthrone derivative is characterized by ¹H- and ¹³C-NMR spectroscopy and high-resolution mass spectrometry. The photophysical properties of the [...] Read more.

The present work describes the facile synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one via a Sonogashira coupling reaction. The structure of the synthesized benzanthrone derivative is characterized by ¹H- and ¹³C-NMR spectroscopy and high-resolution mass spectrometry. The photophysical properties of the title compound are investigated by means of UV-Vis and fluorescence spectroscopy in various organic solvents. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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4 pages, 361 KiB

Open AccessShort Note

4,7-Bis(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine

by Timofey N. Chmovzh and Oleg A. Rakitin

Molbank 2022, 2022(3), M1441; https://doi.org/10.3390/M1441 - 8 Sep 2022

Cited by 1 | Viewed by 1587

Abstract

Donor-acceptor-donor (D-A-D) type molecules are of interest as components in organic light emitting diodes (OLEDs). In this communication, 4,7-bis(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine was obtained by two successive reactions—aromatic nucleophilic substitution S_NAr and Buchwald-Hartwig cross-coupling reaction. The structure of [...] Read more.

Donor-acceptor-donor (D-A-D) type molecules are of interest as components in organic light emitting diodes (OLEDs). In this communication, 4,7-bis(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine was obtained by two successive reactions—aromatic nucleophilic substitution S_NAr and Buchwald-Hartwig cross-coupling reaction. The structure of newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR, IR and UV spectroscopy and mass-spectrometry. The luminescent properties of the title compound were studied. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

7 pages, 1961 KiB

Open AccessCommunication

Synthesis of Bisoxazole and Bromo-substituted Aryloxazoles

by Sambasivarao Kotha and Subba Rao Cheekatla

Molbank 2022, 2022(3), M1440; https://doi.org/10.3390/M1440 - 6 Sep 2022

Viewed by 1874

Abstract

Herein, we report a bisoxazole derivative as well as a bromo-substituted oxazole derivatives via a simple approach. The synthesis begins with an inexpensive and readily available starting material, such as 2,5-dimethoxybenzaldehyde, hydroquinone, and p-toluenesulfonylmethyl isocyanide (TosMIC). This approach relies on the Van [...] Read more.

Herein, we report a bisoxazole derivative as well as a bromo-substituted oxazole derivatives via a simple approach. The synthesis begins with an inexpensive and readily available starting material, such as 2,5-dimethoxybenzaldehyde, hydroquinone, and p-toluenesulfonylmethyl isocyanide (TosMIC). This approach relies on the Van Leusen oxazole method and electrophilic aromatic bromination. The structures of bisoxazole and bromosubstituted aryloxazoles were fully supported by spectroscopic methods (IR, NMR, and HRMS) and further established using single crystal X-ray diffraction studies. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1364 KiB

Open AccessShort Note

Dichloro{4-(4-chlorophenoxy)phthalazin-1-yl} methylphosphonic dichloride

by Dyhia Amrane, Omar Khoumeri, Patrice Vanelle and Nicolas Primas

Molbank 2022, 2022(3), M1439; https://doi.org/10.3390/M1439 - 5 Sep 2022

Viewed by 1737

Abstract

As part of our ongoing scaffold-hopping work on an antiplasmodial 2-trichloromethylquinazoline scaffold, we aimed to explore the 1-trichloromethylphthalazine scaffold as a potential new antimalarial series. Using previously chlorination conditions described by our lab to obtain a trichloromethyl group from a methyl group, we [...] Read more.

As part of our ongoing scaffold-hopping work on an antiplasmodial 2-trichloromethylquinazoline scaffold, we aimed to explore the 1-trichloromethylphthalazine scaffold as a potential new antimalarial series. Using previously chlorination conditions described by our lab to obtain a trichloromethyl group from a methyl group, we did not obtain the target compound; instead, we obtained a dichloro methylphosphonic dichloride side product 3. The nature of this compound was then characterized by NMR, HRMS and X-ray crystallography. The same issue was previously reported by Kato et al., starting from the 2-methyl-3-nitropyridine. Finally, compound 3, although not cytotoxic, was not active against P. falciparum, the parasite responsible for human malaria. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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9 pages, 612 KiB

Open AccessShort Note

1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide

by Reinis Ozolins, Mara Plotniece, Karlis Pajuste, Reinis Putralis, Nadiia Pikun, Arkadij Sobolev, Aiva Plotniece and Martins Rucins

Molbank 2022, 2022(3), M1438; https://doi.org/10.3390/M1438 - 2 Sep 2022

Cited by 3 | Viewed by 2117

Abstract

A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of [...] Read more.

A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of bromine with 4-(anthracen-9-yl)pyridine, produced the desired 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide. The obtained target compound was fully characterized by the IR, ¹H NMR, ¹³C NMR and HRMS data. Studies of the self-assembling properties and characterization of the nanoparticles obtained by the ethanol injection method were performed using dynamic light scattering (DLS) measurements. DLS measurement data showed that 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide produced liposomes that had average diameters of 200 nm when the samples were freshly prepared, and 140 nm after 7 days or 1 month storage. The PDI values of the samples were approximately 0.50 and their zeta-potential values were approximately 41 mV when the samples were freshly prepared, and 33 mV after storage. The obtained nanoparticles were stored at room temperature for one month and remained stable during that period. The mean molecular area of the cationic 1,4-DHP-anthracene hybrid 4 was 118 Å², while the mean molecular area of the cationic 1,4-DHP 5 without anthracene substituents was only 83 Å². The photoluminescence quantum yield (PLQY) value for the EtOH solution of the 1,4-DHP derivative 4 was 10.8%, but for the 1,4-DHP derivative 5 it was only 1.8%. These types of compounds could be used as synthetic lipids in the further development of prospective theranostic delivery systems. Full article

(This article belongs to the Collection Heterocycle Reactions)

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6 pages, 1497 KiB

Open AccessShort Note

(S)-3-(3-((7-Ethynyl-9H-pyrimido[4,5-b]indol-4-yl)amino)piperidin-1-yl)propanenitrile

by Stanislav Andreev, Nicole Plank, Dieter Schollmeyer and Pierre Koch

Molbank 2022, 2022(3), M1437; https://doi.org/10.3390/M1437 - 31 Aug 2022

Viewed by 1724

Abstract

The title compound (S)-3-(3-((7-ethynyl-9H-pyrimido[4,5-b]indol-4-yl)amino)piperidin-1-yl)propanenitrile (2) was synthesized in five steps, starting from 4-chloro-7-iodo-9H-pyrimido[4,5-b]indole (3), and was characterized by ¹H-NMR, ¹³C-NMR, MS and HPLC. Moreover, its structure was [...] Read more.

The title compound (S)-3-(3-((7-ethynyl-9H-pyrimido[4,5-b]indol-4-yl)amino)piperidin-1-yl)propanenitrile (2) was synthesized in five steps, starting from 4-chloro-7-iodo-9H-pyrimido[4,5-b]indole (3), and was characterized by ¹H-NMR, ¹³C-NMR, MS and HPLC. Moreover, its structure was confirmed by single crystal X-ray diffraction. Pyrimido[4,5-b]indole 2 demonstrated an IC₅₀ value of 2.24 µM in a NanoBRET^TM TE intracellular glycogen synthase kinase-3β assay. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

4 pages, 530 KiB

Open AccessShort Note

N′¹,N′⁴-bis(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylidene)succinohydrazide

by Taishu Kawada, Katsuhito Kino, Yoshihiko Matsuzawa, Masayuki Morikawa, Yasuko Okamoto, Takanobu Kobayashi and Yoshiyuki Tanaka

Molbank 2022, 2022(3), M1436; https://doi.org/10.3390/M1436 - 30 Aug 2022

Cited by 1 | Viewed by 1620

Abstract

The title compound, N′¹,N′⁴-bis(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylidene)succinohydrazide (1), was obtained by the reaction of formylmethylflavin and succinic acid dihydrazide. The product 1 was characterized by ¹H-NMR, ¹³C-NMR, HRMS and UV. Full article

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6 pages, 1664 KiB

Open AccessShort Note

(9R,9aS,12aR,13S)-9,13-Diphenyl-9,9a,12a,13-tetrahydro-9,13-methanotriphenyleno[2,3-c]furan-10,12,14-trione

by Corrin Blake, Brian A. Chalmers, Lewis A. Clough, Dylan Clunie, David B. Cordes, Tomas Lebl, Timothy R. McDonald, Siobhan R. Smith, Elliott Stuart-Morrison and Iain A. Smellie

Molbank 2022, 2022(3), M1435; https://doi.org/10.3390/M1435 - 28 Aug 2022

Cited by 1 | Viewed by 1969

Abstract

X-ray crystallography was used to characterise the title compound for the first time, and the ¹H NMR, ¹³C NMR and IR spectroscopic data from earlier reports were also updated. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

5 pages, 382 KiB

Open AccessShort Note

Methyl 2-((3-(3-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)thio)acetate

by Maja Molnar, Mario Komar and Igor Jerković

Molbank 2022, 2022(3), M1434; https://doi.org/10.3390/M1434 - 25 Aug 2022

Cited by 1 | Viewed by 1861

Abstract

A green synthetic procedure was developed for the two-step synthesis of methyl 2-((3-(3-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)thio)acetate from anthranilic acid, using two green chemistry approaches: utilization of the DES and microwave-induced synthesis. The first step includes a synthesis of 2-mercapto-3-(3-methoxyphenyl)quinazolin-4(3H)-one which was performed in choline [...] Read more.

A green synthetic procedure was developed for the two-step synthesis of methyl 2-((3-(3-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)thio)acetate from anthranilic acid, using two green chemistry approaches: utilization of the DES and microwave-induced synthesis. The first step includes a synthesis of 2-mercapto-3-(3-methoxyphenyl)quinazolin-4(3H)-one which was performed in choline chloride:urea DES. In the second step S-alkylation of 2-mercapto-3-(3-methoxyphenyl)quinazolin-4(3H)-one was performed in a microwave-induced reaction. The desired compound was successfully obtained in a yield of 59% and was characterized by different spectral methods. Full article

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6 pages, 955 KiB

Open AccessShort Note

[N,N′-Di-tert-butyl-P,P-diphenylphosphinimidic Amidato-κN,κN′]chlorosilicon-κSi-tetracarbonyliron

by Shintaro Takahashi, Kazuki Nakaya, Akihiko Ishii and Norio Nakata

Molbank 2022, 2022(3), M1433; https://doi.org/10.3390/M1433 - 25 Aug 2022

Cited by 2 | Viewed by 1710

Abstract

The title complex {[Ph₂P(tBuN)₂](Cl)Si:->Fe(CO)₄} (2) was synthesized via the reaction of chlorosilylene [Ph₂P(tBuN)₂]SiCl (1), supported by an iminophosphonamide ligand with Fe(CO)₅ in THF. The [...] Read more.

The title complex {[Ph₂P(tBuN)₂](Cl)Si:->Fe(CO)₄} (2) was synthesized via the reaction of chlorosilylene [Ph₂P(tBuN)₂]SiCl (1), supported by an iminophosphonamide ligand with Fe(CO)₅ in THF. The molecular structure of 2 was fully characterized by NMR (¹H, ¹³C, ²⁹Si, and ³¹P) and IR spectroscopies, as well as single-crystal X-ray diffraction (SCXRD) analysis. In the SCXRD analysis of 2, the silylene ligand was located in the axial positions of the coordination sphere of the central iron atom and other sites were occupied by carbonyl ligands. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 821 KiB

Open AccessShort Note

3-Phenyl-3H-naphtho[1,2-e][1,2,3]oxadiazine

by Alia D. Aouant and George Varvounis

Molbank 2022, 2022(3), M1432; https://doi.org/10.3390/M1432 - 24 Aug 2022

Viewed by 1905

Abstract

In this study, we considered the reaction of (E)-1-[(2-phenylhydrazono)methyl]naphthalen-2-ol with iodobenzene diacetate in dichloromethane-produced novel 3-phenyl-3H-naphtho[1,2-e][1,2,3]oxadiazine in 11% yield. By analogy to previously published work, we suggested that the reaction proceeds via the intermediacy of an o [...] Read more.

In this study, we considered the reaction of (E)-1-[(2-phenylhydrazono)methyl]naphthalen-2-ol with iodobenzene diacetate in dichloromethane-produced novel 3-phenyl-3H-naphtho[1,2-e][1,2,3]oxadiazine in 11% yield. By analogy to previously published work, we suggested that the reaction proceeds via the intermediacy of an o-naphthoquinone azomethide that undergoes conjugated 6π-electrocylization to produce the product. 1D, 2D NMR, HRMS, IR, and UV-VIS spectra provided information that supported the structure of the product. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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4 pages, 462 KiB

Open AccessShort Note

3-Methoxy-5-methyl-12-phenylbenzacridinium Iodide

by Malokhat Uktamova, Rintaro Koga, Fotima Mukhamedjonova, Tursunali Kholikov, Bakhtiyor Ibragimov, Kohei Torikai and Khamid Khodjaniyazov

Molbank 2022, 2022(3), M1431; https://doi.org/10.3390/M1431 - 22 Aug 2022

Viewed by 1816

Abstract

N-alkylacridinium derivatives are some of the most popular azo dye templates. Herein, we report the synthesis of 3-methoxy-5-methyl-12-phenylbenzacridinium iodide (MMPBAI) via N-alkylation. The structure of MMPBAI was elucidated using ¹H Nuclear magnetic resonance (NMR), ¹³C NMR, Electronspray ionization mass [...] Read more.

N-alkylacridinium derivatives are some of the most popular azo dye templates. Herein, we report the synthesis of 3-methoxy-5-methyl-12-phenylbenzacridinium iodide (MMPBAI) via N-alkylation. The structure of MMPBAI was elucidated using ¹H Nuclear magnetic resonance (NMR), ¹³C NMR, Electronspray ionization mass spectrometry (ESI-MS), and Fourier-transform infrared spectroscopy (FT-IR). MMPBAI could not visualize double-stranded DNA in agarose gel, although the structural core would still be interesting as a template for new azo dyes. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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5 pages, 1563 KiB

Open AccessShort Note

1-(4-Fluorobenzoyl)-9H-carbazole

by Markus Laube, Jonas König, Martin Köckerling and Torsten Kniess

Molbank 2022, 2022(3), M1430; https://doi.org/10.3390/M1430 - 19 Aug 2022

Viewed by 1939

Abstract

1-(4-Fluorobenzoyl)-9H-carbazole (1) was synthesized, starting from 9H-carbazole and 4-fluorobenzonitrile, by Friedel–Crafts acylation, using boron trichloride to direct the substitution in 1-position. Single-crystal X-ray diffraction analysis unambiguously revealed the molecular structure of 1. Full article

(This article belongs to the Section Structure Determination)

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9 pages, 2028 KiB

Open AccessShort Note

Chlorido-(η⁶-p-cymene)-(bis(pyrazol-1-yl)methane-κ²N,N′)Osmium(II) Tetrafluoroborate, C₁₇H₂₂BClF₄N₄Os

by Allen Mambanda, Amos K. Kanyora, Peter Ongoma, Joel Gichumbi and Reinner O. Omondi

Molbank 2022, 2022(3), M1429; https://doi.org/10.3390/M1429 - 18 Aug 2022

Viewed by 1831

Abstract

The powder of the arene osmium(II) complex, [Os(II)(dpzm)(η⁶-p-cym)Cl]BF₄ (dpzm = di(1H-pyrazol-1-yl)methane; η⁶-p-cym = para-cymene), with a formula of C₁₇H₂₂BClF₄N₄Os (referred to herein [...] Read more.

The powder of the arene osmium(II) complex, [Os(II)(dpzm)(η⁶-p-cym)Cl]BF₄ (dpzm = di(1H-pyrazol-1-yl)methane; η⁶-p-cym = para-cymene), with a formula of C₁₇H₂₂BClF₄N₄Os (referred to herein as 1) was isolated from the reaction of [(η⁶-p-cym)Os(μ-Cl)(Cl)]₂ with dpzm dissolved in acetonitrile and under a flow of nitrogen gas. It was characterized by spectroscopic techniques (viz., FTIR, ¹H NMR, UV-Visible absorption). Yellow crystal blocks of 1 were grown by the slow evaporation from the methanolic solution of its powder. The single-crystal X-ray structure of 1 was solved by diffraction analysis on a Bruker APEX Duo CCD area detector diffractometer using the Cu(K_α), λ = 1.54178 Å as the radiation source, and 1 crystallizes in the monoclinic crystal system and the C2/c (no. 15) space group. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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Graphical abstract

4 pages, 510 KiB

Open AccessShort Note

4,7-Di(9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine

by Timofey N. Chmovzh, Timofey A. Kudryashev, Karim S. Gaisin and Oleg A. Rakitin

Molbank 2022, 2022(3), M1428; https://doi.org/10.3390/M1428 - 17 Aug 2022

Viewed by 1682

Abstract

Donor–acceptor–donor (D–A–D)-type molecules are considered as a promising class of NIR fluorescence materials. In this communication, 4,7-di(9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained by dehydrogenation of 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in toluene. The structure of the synthesized compound was established [...] Read more.

Donor–acceptor–donor (D–A–D)-type molecules are considered as a promising class of NIR fluorescence materials. In this communication, 4,7-di(9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained by dehydrogenation of 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in toluene. The structure of the synthesized compound was established by elemental analysis; high-resolution mass spectrometry; ¹H, ¹³C NMR, IR, and UV spectroscopy; and mass spectrometry. The photophysical properties of the title compound were studied and compared with spectral data of the [1,2,5]thiadiazolo[3,4-d]pyridazine analogue. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1118 KiB

Open AccessCommunication

Synthesis of 4-(tert-Butyldimethylsilyl)-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine

by Rasma Kroņkalne, Rūdolfs Beļaunieks and Māris Turks

Molbank 2022, 2022(3), M1427; https://doi.org/10.3390/M1427 - 16 Aug 2022

Cited by 1 | Viewed by 2053

Abstract

S_N2 rection between 4-(tert-butyldimethylsilyl)hex-5-yn-1-yl 4-methylbenzenesulfonate and NaN₃ in DMF at 80 °C provided (6-azidohex-1-yn-3-yl)(tert-butyl)dimethylsilane intermediate, which underwent in situ intramolecular thermal Huisgen azide–alkyne cycloaddition reaction. This one-pot process gave 4-(tert-butyldimethylsilyl)-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine in 78% yield. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1146 KiB

Open AccessCommunication

S_NAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde

by Jorge Trilleras, Alfredo Pérez-Gamboa and Jairo Quiroga

Molbank 2022, 2022(3), M1426; https://doi.org/10.3390/M1426 - 12 Aug 2022

Cited by 1 | Viewed by 2856

Abstract

We report the experimental results of unexpected aromatic nucleophilic substitution reaction products on 2-amino-4,6-dichloropyrimidine-5-carbaldehyde. The isolated compounds are products of amination, solvolysis, and condensation processes under mild and environmentally friendly conditions, due to the influence of structural factors of the starting pyrimidine and [...] Read more.

We report the experimental results of unexpected aromatic nucleophilic substitution reaction products on 2-amino-4,6-dichloropyrimidine-5-carbaldehyde. The isolated compounds are products of amination, solvolysis, and condensation processes under mild and environmentally friendly conditions, due to the influence of structural factors of the starting pyrimidine and a high concentration of alkoxide ions. This method allows the building of pyrimidine-based compound precursors of N-heterocyclic systems. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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4 pages, 374 KiB

Open AccessShort Note

4-Amino-3-(1-{[amino(3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)methylene]hydrazinylidene}ethyl)-1,2,5-oxadiazole 2-Oxide

by Margarita A. Epishina, Alexander S. Kulikov and Leonid L. Fershtat

Molbank 2022, 2022(3), M1425; https://doi.org/10.3390/M1425 - 12 Aug 2022

Viewed by 1895

Abstract

Functionally substituted 1,2,5-oxadiazole 2-oxides (furoxans) are important pharmaceutical scaffolds used for the preparation of various pharmacologically active substances. Furoxans bearing hydrazone functionality are considered as promising drug candidates for the treatment of neglected diseases. However, pharmacologically oriented hydrazones derived from (furoxanyl)amidrazones and acetylfuroxans [...] Read more.

Functionally substituted 1,2,5-oxadiazole 2-oxides (furoxans) are important pharmaceutical scaffolds used for the preparation of various pharmacologically active substances. Furoxans bearing hydrazone functionality are considered as promising drug candidates for the treatment of neglected diseases. However, pharmacologically oriented hydrazones derived from (furoxanyl)amidrazones and acetylfuroxans have remained unknown so far. In this communication, a simple method for the synthesis of 4-amino-3-(1-{[amino(3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)methylene]hydrazinylidene}ethyl)-1,2,5-oxadiazole 2-oxide is described. The structure of the synthesized compound was established by elemental analysis, high-resolution mass spectrometry, ¹H, ¹³C NMR and IR spectroscopy. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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6 pages, 1117 KiB

Open AccessShort Note

Diethyl(benzamido(diisopropoxyphosphoryl)methyl) phosphonate

by Adrián López-Francés, Francisco Palacios, Aitor Maestro and Javier Vicario

Molbank 2022, 2022(3), M1424; https://doi.org/10.3390/M1424 - 11 Aug 2022

Viewed by 1880

Abstract

Bisphosphonates are widely used in medicine and related areas, mainly for the treatment of bone diseases, such as osteoporosis. However, their synthesis is usually performed under harsh reaction conditions. In order to overcome this limitation, the present work illustrates a new synthetic route [...] Read more.

Bisphosphonates are widely used in medicine and related areas, mainly for the treatment of bone diseases, such as osteoporosis. However, their synthesis is usually performed under harsh reaction conditions. In order to overcome this limitation, the present work illustrates a new synthetic route to access the title α-aminobisphosphonate in milder reaction conditions using α-phosphorylated imines as key intermediates. Full article

(This article belongs to the Topic Organocatalysis and Transition-Metal Catalysis: Key Trends in Synthetic Chemistry and Challenges)

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3 pages, 365 KiB

Open AccessShort Note

N,N-Bis(7-nitrobenz[c][1,2,5]oxadiazol-4-yl)cystamine

by Iulia Matei, Dana C. Culita, Victorita Tecuceanu, Anamaria Hanganu and Petre Ionita

Molbank 2022, 2022(3), M1423; https://doi.org/10.3390/M1423 - 8 Aug 2022

Cited by 2 | Viewed by 1607

Abstract

Background: New amino derivatives of NBD type are of high interest due to their strong fluorescence, while compounds containing a disulphide moiety are of high interest in nano-chemistry due to their easiness of attaching to noble nanoparticles. Therefore, in this work a new [...] Read more.

Background: New amino derivatives of NBD type are of high interest due to their strong fluorescence, while compounds containing a disulphide moiety are of high interest in nano-chemistry due to their easiness of attaching to noble nanoparticles. Therefore, in this work a new fluorescent derivative of NBD and cystamine was obtained. Methods: The reaction between cystamine and NBD-chloride occurs straightforwardly, and the isolated new compound was characterized by IR, UV-Vis, fluorescence, ¹H- and ¹³C-NMR, MS, etc. Results: Structural analysis confirmed the proposed structure and highlighted the fluorescence behavior. Conclusions: A new fluorescent derivative of cystamine was obtained and characterized by different means. Full article

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6 pages, 1007 KiB

Open AccessCommunication

Placovinane: 1″β-Ethoxy-6,4′-dimethoxy-3″,3″-dimethyl-1″,2″-dihydropyranoisoflavone, a New Isoflavone Derivative

by Tuyet T. N. Huynh, Lien T. M. Do and Jirapast Sichaem

Molbank 2022, 2022(3), M1422; https://doi.org/10.3390/M1422 - 5 Aug 2022

Viewed by 1619

Abstract

Isoflavonoids possess a 3-phenylchroman skeleton and are the biologically active secondary metabolites of various plants that are used for different health promoting and restoring effects through a variety of mechanisms. Chromatographic separation of the n-hexane extract from the stems of Placolobium vietnamense [...] Read more.

Isoflavonoids possess a 3-phenylchroman skeleton and are the biologically active secondary metabolites of various plants that are used for different health promoting and restoring effects through a variety of mechanisms. Chromatographic separation of the n-hexane extract from the stems of Placolobium vietnamense led to the isolation of a new isoflavone derivative, placovinane (1), together with four known compounds (2–5). The structures of isolated compounds were identified from their spectroscopic data and by comparison with the literature. All isolated compounds were evaluated for their α-glucosidase inhibition. They all exhibited potent α-glucosidase inhibition with IC₅₀ values ranging from 11.0 to 87.3 µM, which was significantly less than the positive control acarbose (IC₅₀ 179 µM). The cytotoxicity of 1 was evaluated against KB, Hep G2, and MCF7 cell lines, and displayed weak cytotoxicity toward KB and Hep G2 cell lines, with the IC₅₀ values of 89.6 and 93.8 μM, respectively. Full article

(This article belongs to the Section Natural Product Chemistry)

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4 pages, 926 KiB

Open AccessShort Note

3-(1-Cyclohexyl-2-(cyclohexylamino)-4-(4-ethoxyphenyl)-6-oxo-1,6-dihydropyrimidin-5-yl)-1-methylquinoxalin-2(1H)-one

by Ekaterina E. Khramtsova, Svetlana O. Kasatkina, Maksim V. Dmitriev and Andrey N. Maslivets

Molbank 2022, 2022(3), M1421; https://doi.org/10.3390/M1421 - 5 Aug 2022

Viewed by 1958

Abstract

The reaction of 3-cyclohexyl-2-(cyclohexylimino)-6-(4-ethoxyphenyl)-5-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)-2,3-dihydro-4H-1,3-oxazin-4-one with ammonium acetate afforded 3-(1-cyclohexyl-2-(cyclohexylamino)-4-(4-ethoxyphenyl)-6-oxo-1,6-dihydropyrimidin-5-yl)-1-methylquinoxalin-2(1H)-one in a good yield. The compound was fully characterized. Full article

(This article belongs to the Collection Heterocycle Reactions)

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8 pages, 3774 KiB

Open AccessShort Note

2,5-Bis((E)-2-ferrocenylvinyl)-N,N,N′,N′-tetrapropylbenzene-1,4-diamine

by Matthias Jochem, Igor Proz, Dieter Schollmeyer and Heiner Detert

Molbank 2022, 2022(3), M1420; https://doi.org/10.3390/M1420 - 4 Aug 2022

Viewed by 1520

Abstract

The synthesis and spectroscopic investigation of an acidochromic phenylenevinylene dye with two ferrocene groups is presented. Full article

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10 pages, 1818 KiB

Open AccessShort Note

3-[(1H-Benzo[d][1,2,3]triazol-1-yl)oxy]propyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

by Ai Jiang, Margrate Anyanwu, Kafai Leong, Jinxin Li, Alessandra Gianoncelli, Paolo Coghi and Giovanni Ribaudo

Molbank 2022, 2022(3), M1419; https://doi.org/10.3390/M1419 - 4 Aug 2022

Cited by 1 | Viewed by 2220

Abstract

We herein report on the synthesis of a pentacyclic triterpene functionalized through derivation of betulinic acid with hydroxybenzotriazole. The compound was fully characterized by proton (¹H-NMR), carbon-13 (¹³C-NMR), heteronuclear single quantum coherence (HSQC) and distortionless enhancement by polarization transfer [...] Read more.

We herein report on the synthesis of a pentacyclic triterpene functionalized through derivation of betulinic acid with hydroxybenzotriazole. The compound was fully characterized by proton (¹H-NMR), carbon-13 (¹³C-NMR), heteronuclear single quantum coherence (HSQC) and distortionless enhancement by polarization transfer (DEPT-135 and DEPT-90) nuclear magnetic resonance. Ultraviolet (UV), and Fourier-transform infrared (FTIR) spectroscopies as well as and high-resolution mass spectrometry (HRMS) were also adopted. Computational studies were conducted to foresee the interactions between compound 3 and phosphodiesterase 9, a relevant target in the field of neurodegenerative diseases. Additionally, preliminary calculation of physico-chemical descriptors was performed to evaluate the drug-likeness of compound 3. Full article

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Molbank, Volume 2022, Issue 3 (September 2022) – 56 articles

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