Molbank

8 pages, 723 KiB

Open AccessCommunication

Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline

by Deiby F. Aparicio Acevedo, Marlyn C. Ortiz Villamizar and Vladimir V. Kouznetsov

Molbank 2024, 2024(1), M1796; https://doi.org/10.3390/M1796 - 21 Mar 2024

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The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using a N-oxidation reaction/C2-amide formation reaction/C4 S_NAr reaction sequence. The structure of the compound was fully characterized by FT-IR, ¹H-, ¹³C-NMR, DEPT-135°, and ESI-MS [...] Read more.

The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using a N-oxidation reaction/C2-amide formation reaction/C4 S_NAr reaction sequence. The structure of the compound was fully characterized by FT-IR, ¹H-, ¹³C-NMR, DEPT-135°, and ESI-MS techniques. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the online SwissADME database. Such derivatives are relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, and antiparasitic properties. Full article

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

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Graphical abstract

8 pages, 1779 KiB

Open AccessCommunication

Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry

by Paul R. Palme, Richard Goddard, Peter Imming and Rüdiger W. Seidel

Molbank 2024, 2024(1), M1795; https://doi.org/10.3390/M1795 - 20 Mar 2024

Viewed by 1564

Abstract

4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title [...] Read more.

4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title compound by means of a nucleophilic aromatic substitution reaction of 4-fluoronitrobenzene and thiomorpholine and structurally characterized it by X-ray crystallography, DFT calculations, and Hirshfeld surface analysis. In the crystal, the molecule exhibits an approximately C_S-symmetric structure, with the nitrogen-bound 4-nitrophenyl group in a quasi axial position on the six-membered thiomorpholine ring in a low-energy chair conformation. The solid-state structure of the title compound is markedly different from that of its morpholine analogue. This can be ascribed to the formation of centrosymmetric dimers through intermolecular C–H···O weak hydrogen bonds involving the methylene groups adjacent to the sulfur atom and face-to-face aromatic stacking. Full article

(This article belongs to the Section Structure Determination)

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Figure 1

10 pages, 1899 KiB

Open AccessCommunication

Butyl (2,2-Dibutoxybutanoyl)-ʟ-Tryptophanate

by Diego Quiroga and Ericsson Coy-Barrera

Molbank 2024, 2024(1), M1794; https://doi.org/10.3390/M1794 - 19 Mar 2024

Viewed by 1334

Abstract

The multicomponent reaction between ʟ-tryptophan 1, 2-oxobutanoic acid 2, and 1-butanol in the presence of SiMe₃Cl was studied using microwave irradiation conditions. The main product was identified as an unreported acetal-containing compound, namely, butyl (2,2-dibutoxybutanoyl)-ʟ-tryptophanate (3), yielding [...] Read more.

The multicomponent reaction between ʟ-tryptophan 1, 2-oxobutanoic acid 2, and 1-butanol in the presence of SiMe₃Cl was studied using microwave irradiation conditions. The main product was identified as an unreported acetal-containing compound, namely, butyl (2,2-dibutoxybutanoyl)-ʟ-tryptophanate (3), yielding 89%. NMR experiments demonstrated that the adjacent methylene protons of the acetal group appeared as two signals exhibiting their behavior as diastereotopic protons. DFT/B3LYP calculations revealed an asymmetric molecular structure with specific angles, leading to an explanation of the NMR results. The calculated chemical shifts showed slight differences with the experimental values and suggested magnetic anisotropy and inductive deprotection around the methylene hydrogen atoms in the acetal location. The reaction mechanism was proposed in which SiMe₃Cl plays a crucial role by promoting water removal through key steps. Full article

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

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8 pages, 973 KiB

Open AccessCommunication

Synthesis and In Vitro Antibacterial Evaluation of Mannich Base Nitrothiazole Derivatives

by Phelelisiwe S. Dube, Dylan Hart, Lesetja J. Legoabe, Audrey Jordaan, Digby F. Warner and Richard M. Beteck

Molbank 2024, 2024(1), M1793; https://doi.org/10.3390/M1793 - 18 Mar 2024

Viewed by 1583

Abstract

Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we [...] Read more.

Nitrothiazole derivatives have been reported to exhibit activity against aerobic, anaerobic, and microaerophilic bacteria. This activity profile makes the nitrothiazole compound class an ideal lead source against Mycobacterium tuberculosis, which flourishes in varied environments with different oxygen concentrations. In this work, we investigated six nitrothiazole derivatives for antitubercular activity. The compounds exhibited potent activity, with compounds 9 and 10 possessing an equipotent MIC₉₀ value of 0.24 µM. The compounds were investigated for cytotoxicity against HEK293 cells and hemolysis against red blood cells, and they demonstrated no cytotoxicity nor hemolytic effects, suggesting they possess inherent antitubercular activity. Full article

(This article belongs to the Topic Towards the Sustainable Synthesis of Biologically Active Molecules in Green Solvents)

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4 pages, 338 KiB

Open AccessShort Note

5-(9-(p-Tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde

by Nikita S. Gudim, Ekaterina A. Knyazeva and Oleg A. Rakitin

Molbank 2024, 2024(1), M1792; https://doi.org/10.3390/M1792 - 14 Mar 2024

Cited by 1 | Viewed by 1371

Abstract

Donor–π spacer–acceptor (D–π–A) dyes are among the most attractive structures for the design of organic dye-sensitized solar cells (DSSCs). Typically, the key intermediates for these sensitizers are D–π compounds containing an aldehyde group to which an anchor acceptor group is attached via the [...] Read more.

Donor–π spacer–acceptor (D–π–A) dyes are among the most attractive structures for the design of organic dye-sensitized solar cells (DSSCs). Typically, the key intermediates for these sensitizers are D–π compounds containing an aldehyde group to which an anchor acceptor group is attached via the Knoevenagel reaction. In this communication, 5-(9-(p-tolyl)-2,3,4,4a,9,9a-hexahydro-1H-1,4-methanocarbazol-6-yl)thiophene-2-carbaldehyde was prepared via the Suzuki cross-coupling reaction. The structure of the newly synthesized compound was established by means of high-resolution mass spectrometry, ¹H NMR, ¹³C NMR, IR, and UV–Vis spectroscopy. The title compound would be used in the synthesis of sensitizers for DSSCs. Full article

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

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Scheme 1

6 pages, 688 KiB

Open AccessShort Note

1-(3,4-Dimethoxyphenyl)-3-(4-methoxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one

by Anna Nacher-Luis and Isidro M. Pastor

Molbank 2024, 2024(1), M1791; https://doi.org/10.3390/M1791 - 12 Mar 2024

Viewed by 1480

Abstract

The study of new catalytic protocols for the synthesis of organic compounds with a more sustainable perspective is of interest. The use of ionic organic solids, such as 1,3-bis(carboxymethyl)imidazolium chloride as a catalyst has allowed the Michael addition of N-heterocycles to chalcones. This [...] Read more.

The study of new catalytic protocols for the synthesis of organic compounds with a more sustainable perspective is of interest. The use of ionic organic solids, such as 1,3-bis(carboxymethyl)imidazolium chloride as a catalyst has allowed the Michael addition of N-heterocycles to chalcones. This methodology has been applied to the unique preparation of the potential bioactive compound 1-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one with moderate yield, due to the retro-Michael reaction. Both synthetic reactions (i.e., preparation of chalcone and triazole Michael-addition to chalcone) have good green metrics. Full article

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Scheme 1

6 pages, 1119 KiB

Open AccessShort Note

(E)-1-(1-(Benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine

by Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki and Gamal A. El-Hiti

Molbank 2024, 2024(1), M1790; https://doi.org/10.3390/M1790 - 11 Mar 2024

Viewed by 1378

Abstract

The reaction of a mixture of equimolar quantities of 2-acetylbenzofuran and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for two hours yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude product was purified by crystallization using dimethylformamide to provide the [...] Read more.

The reaction of a mixture of equimolar quantities of 2-acetylbenzofuran and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for two hours yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude product was purified by crystallization using dimethylformamide to provide the title heterocycle in a 90% yield. The structure of the new heterocycle was confirmed through X-ray diffraction and spectral analyses. Full article

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Graphical abstract

6 pages, 1080 KiB

Open AccessShort Note

1-(2,4-Dinitrophenyl)-2-((Z)-2-((E)-4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine

by Bakr F. Abdel-Wahab, Hanan A. Mohamed, Benson M. Kariuki and Gamal A. El-Hiti

Molbank 2024, 2024(1), M1789; https://doi.org/10.3390/M1789 - 11 Mar 2024

Viewed by 1403

Abstract

The reaction of (E)-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one and (2,4-dinitrophenyl)hydrazine in boiling ethanol containing hydrochloric acid (0.2 mL; 37%) for 1.5 h gave 1-(2,4-dinitrophenyl)-2-(2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine in a 90% yield. Various spectral analyses, including NMR, and X-ray crystallography established the structure of the newly synthesized hydrazone. Full article

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Graphical abstract

4 pages, 327 KiB

Open AccessCommunication

Bis(2,2,6,6-tetramethyl-1-(λ¹-oxidaneyl)piperidin-4-yl) 3,3′-((2-hydroxyethyl)azanediyl)dipropionate

by Roman P. Kustin, Oleg V. Levin, Sofia S. Filippova and Elena V. Alekseeva

Molbank 2024, 2024(1), M1788; https://doi.org/10.3390/M1788 - 8 Mar 2024

Viewed by 1437

Abstract

TEMPO-containing conductive polymers are used in organic electronics due to their electrochemical properties. One of significant limitations in developing such materials is the structural modification by several TEMPO moieties. Here, we report a synthesis of the first-generation dendrimer containing two TEMPO fragments, bis(2,2,6,6-tetramethyl-1-(λ [...] Read more.

TEMPO-containing conductive polymers are used in organic electronics due to their electrochemical properties. One of significant limitations in developing such materials is the structural modification by several TEMPO moieties. Here, we report a synthesis of the first-generation dendrimer containing two TEMPO fragments, bis(2,2,6,6-tetramethyl-1-(λ¹-oxidaneyl)piperidin-4-yl) 3,3′-((2-hydroxyethyl)azanediyl)dipropionate, that can be implemented into a conductive polymer structure. The resulting product was characterized using ¹H and ¹³C nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectroscopy (HRMS). Full article

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Scheme 1

7 pages, 1573 KiB

Open AccessCommunication

Synthesis and Monoamine Oxidase Inhibition Properties of 4-(2-Methyloxazol-4-yl)benzenesulfonamide

by Anton A. Shetnev, Julia A. Efimova, Mikhail K. Korsakov, Anél Petzer and Jacobus P. Petzer

Molbank 2024, 2024(1), M1787; https://doi.org/10.3390/M1787 - 6 Mar 2024

Cited by 1 | Viewed by 1553

Abstract

4-(2-Methyloxazol-4-yl)benzenesulfonamide was synthesized by the reaction of 4-(2-bromoacetyl)benzenesulfonamide with an excess of acetamide. The compound was evaluated as a potential inhibitor of human monoamine oxidase (MAO) A and B and was found to inhibit these enzymes with IC₅₀ values of 43.3 and [...] Read more.

4-(2-Methyloxazol-4-yl)benzenesulfonamide was synthesized by the reaction of 4-(2-bromoacetyl)benzenesulfonamide with an excess of acetamide. The compound was evaluated as a potential inhibitor of human monoamine oxidase (MAO) A and B and was found to inhibit these enzymes with IC₅₀ values of 43.3 and 3.47 μM, respectively. The potential binding orientation and interactions of the inhibitor with MAO-B were examined by molecular docking, and it was found that the sulfonamide group binds and interacts with residues of the substrate cavity. 4-(2-Methyloxazol-4-yl)benzenesulfonamide showed no cytotoxic effect against human stromal bone cell line (HS-5) in the concentration range of 1–100 µmol. Thus, the new selective MAO-B inhibitor was identified, which may be used as the lead compound for the development of antiparkinsonian agents. Full article

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5 pages, 1111 KiB

Open AccessShort Note

Bis(N-tert-butylacetamido)(dimethylamido)(chloro)titanium

by Dennis M. Seth, Jr. and Rory Waterman

Molbank 2024, 2024(1), M1786; https://doi.org/10.3390/M1786 - 6 Mar 2024

Viewed by 1449

Abstract

The titanium amidate compound bis(N-tert-butylacetamido)(dimethylamido)(chloro)titanium was synthesized by the protonolysis of tris(dimethylamido)(chloro)titanium and structurally characterized by ¹H and ¹³C NMR spectroscopy as well as X-ray diffraction. The compound does not appear to react cleanly nor readily with routine alkylating [...] Read more.

The titanium amidate compound bis(N-tert-butylacetamido)(dimethylamido)(chloro)titanium was synthesized by the protonolysis of tris(dimethylamido)(chloro)titanium and structurally characterized by ¹H and ¹³C NMR spectroscopy as well as X-ray diffraction. The compound does not appear to react cleanly nor readily with routine alkylating agents such as sec-butyllithium, benzyl potassium, or trimethylsilyl methyllithium. Full article

(This article belongs to the Section Structure Determination)

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7 pages, 558 KiB

Open AccessShort Note

2-((5-(3-(2-Fluorophenyl)acryloyl)-4-methylthiazol-2-yl)amino)isoindoline-1,3-dione

by Olha-Maria Fedusevych, Andrii Lozynskyi, Marta Sulyma and Roman Lesyk

Molbank 2024, 2024(1), M1785; https://doi.org/10.3390/M1785 - 6 Mar 2024

Cited by 1 | Viewed by 1536

Abstract

In this work, the title compound was synthesized via the Claisen–Schmidt condensation of a 2-((5-acetyl-4-methylthiazol-2-yl)amino)isoindoline-1,3-dione with 2-fluorobenzaldehyde. The structure of the synthesized compound (yield 62%) was confirmed by ¹H, ¹³C NMR, and LC–MS spectra. According to US NCI protocols, the compound [...] Read more.

In this work, the title compound was synthesized via the Claisen–Schmidt condensation of a 2-((5-acetyl-4-methylthiazol-2-yl)amino)isoindoline-1,3-dione with 2-fluorobenzaldehyde. The structure of the synthesized compound (yield 62%) was confirmed by ¹H, ¹³C NMR, and LC–MS spectra. According to US NCI protocols, the compound displayed a high level of antimitotic activity against tested human tumor cells, with mean GI₅₀/TGI values of 15.72/50.68 μM. The drug-like properties of the synthesized compound were evaluated using SwissAdme, revealing satisfactory drug-like parameters, and it presents interest for the design of new synthetic agents with biological activity. Full article

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5 pages, 620 KiB

Open AccessShort Note

(10E,15Z)-12-(Dimethylsulfonio)-9,13-dihydroxyoctadeca-10,15-dienoate

by Haruka Nishino, Bo-Tao Zhang, Hajime Uchida, Michiya Kamio, Hiroshi Nagai and Masayuki Satake

Molbank 2024, 2024(1), M1784; https://doi.org/10.3390/M1784 - 3 Mar 2024

Viewed by 1721

Abstract

A novel oxylipin, okeanoate (1), was isolated from the Okinawan cyanobacterium Okeania hirsuta. The structure of 1 was elucidated based on spectroscopic data including 1D and 2D NMR, as well as high-resolution mass spectrometry. This is the first oxylipin with [...] Read more.

A novel oxylipin, okeanoate (1), was isolated from the Okinawan cyanobacterium Okeania hirsuta. The structure of 1 was elucidated based on spectroscopic data including 1D and 2D NMR, as well as high-resolution mass spectrometry. This is the first oxylipin with a dimethylsulfonium moiety in the middle of the hydrocarbon chain. Full article

(This article belongs to the Section Natural Product Chemistry)

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Figure 1

9 pages, 3101 KiB

Open AccessCommunication

Synthesis of (Z)-3-Allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one and Determination of Its Crystal Structure

by Bastien Moreno, Isabelle Jourdain, Michael Knorr, Sarra Boudriga, Carsten Strohmann and Tobias Schrimpf

Molbank 2024, 2024(1), M1783; https://doi.org/10.3390/M1783 - 1 Mar 2024

Cited by 1 | Viewed by 1701

Abstract

To extend the existing library of arylidenerhodanines which display a potential biological activity, 3-N-allylrhodanine 1 was condensed under Knoevenagel conditions with p-nitrobenzaldehyde in acetic acid to afford the π-conjugated heterocyclic compound 3-allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 2. Compound 2 was characterized by IR [...] Read more.

To extend the existing library of arylidenerhodanines which display a potential biological activity, 3-N-allylrhodanine 1 was condensed under Knoevenagel conditions with p-nitrobenzaldehyde in acetic acid to afford the π-conjugated heterocyclic compound 3-allyl-5-(4-nitrobenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 2. Compound 2 was characterized by IR and NMR spectroscopy, and its UV-vis spectrum was compared with that of compound 3-allyl-5-(4-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one 3. The molecular structure is ascertained by a single-crystal X-ray diffraction study performed at 100 K. Full article

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

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5 pages, 561 KiB

Open AccessShort Note

3-(2-Chloroethoxy)-1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde

by Gabrielė Varvuolytė, Aurimas Bieliauskas, Neringa Kleizienė, Asta Žukauskaitė and Algirdas Šačkus

Molbank 2024, 2024(1), M1782; https://doi.org/10.3390/M1782 - 1 Mar 2024

Cited by 1 | Viewed by 1635

Abstract

Herein, we describe the synthesis of 3-(2-chloroethoxy)-1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde via the Vilsmeier-Haack reaction. The structure of this previously unreported compound is thoroughly elucidated through NMR, FT-IR spectroscopy and HRMS spectrometry. Full article

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

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6 pages, 1230 KiB

Open AccessShort Note

(N,N′-Di-tert-butyl-S-phenylsulfinimidamidato-κN,κN′)-chlorogermanium-κGe-chloro(η²,η²-cycloocta-1,5-diene)rhodium

by Narimi Hosoda, Akihiko Ishii and Norio Nakata

Molbank 2024, 2024(1), M1781; https://doi.org/10.3390/M1781 - 28 Feb 2024

Viewed by 1594

Abstract

The title complex [{PhS(tBuN)₂}(Cl)Ge:→RhCl(cod)] (2) was synthesized by the reaction of three-coordinated chlorogermylene, [PhS(tBuN)₂]GeCl (1), supported by a diimidosulfinate ligand with a half equivalent of [RhCl(cod)]₂ in benzene. The molecular [...] Read more.

The title complex [{PhS(tBuN)₂}(Cl)Ge:→RhCl(cod)] (2) was synthesized by the reaction of three-coordinated chlorogermylene, [PhS(tBuN)₂]GeCl (1), supported by a diimidosulfinate ligand with a half equivalent of [RhCl(cod)]₂ in benzene. The molecular structure of 2 was determined by ¹H and ¹³C NMR spectroscopies and single-crystal X-ray diffraction (SCXRD) analysis. The electronic property of germylene 1 was assessed by determining the Tolman electronic parameter of the corresponding cis-dicarbonyl Rh(I) complex, [{PhS(tBuN)₂}(Cl)Ge:→RhCl(CO)₂] (3), that was prepared by the treatment of 2 with carbon monoxide. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 2358 KiB

Open AccessShort Note

1,4-Bis(2-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine

by Nikolai S. Li-Zhulanov, Artem D. Rogachev, Yuri V. Gatilov, Konstantin P. Volcho and Nariman F. Salakhutdinov

Molbank 2024, 2024(1), M1780; https://doi.org/10.3390/M1780 - 28 Feb 2024

Viewed by 1328

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. Full article

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12 pages, 1766 KiB

Open AccessCommunication

5-Fluorouracil/Coumarin and 5-Fluorouracil/Chromone Hybrids: Synthesis and Drug-Likeness Modeling

by Laura Giraldo-Arroyave, Andrés F. Yepes and Wilson Cardona-Galeano

Molbank 2024, 2024(1), M1779; https://doi.org/10.3390/M1779 - 28 Feb 2024

Cited by 1 | Viewed by 1442

Abstract

A series of 5-fluorouracil/coumarin and 5-fluorouracil/chromone hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds and all intermediates were elucidated by spectroscopic analysis. Furthermore, pharmacokinetic and drug-like computations taken together indicated that the novel [...] Read more.

A series of 5-fluorouracil/coumarin and 5-fluorouracil/chromone hybrids were synthesized with good yields using click chemistry as the key step. The structures of these compounds and all intermediates were elucidated by spectroscopic analysis. Furthermore, pharmacokinetic and drug-like computations taken together indicated that the novel hybrids have a strong possibility to advance to further biological studies. Full article

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Graphical abstract

5 pages, 764 KiB

Open AccessShort Note

2-Methyl-4-Oxo-4,5-Dihydro-1H-Pyrrole-3-Carboxylic Acid Phenylamide

by Plamen Angelov and Pavel Yanev

Molbank 2024, 2024(1), M1778; https://doi.org/10.3390/M1778 - 28 Feb 2024

Viewed by 1487

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 [...] Read more.

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. Full article

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

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5 pages, 1296 KiB

Open AccessShort Note

2,3,5,6-Tetrafluoro-[N-(3-aminopropyl)-ε-caprolactam]-4-pyridine

by Chadron M. Friesen, Nathan J. Weeks and Scott T. Iacono

Molbank 2024, 2024(1), M1777; https://doi.org/10.3390/M1777 - 22 Feb 2024

Cited by 1 | Viewed by 1410

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. Full article

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

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6 pages, 1438 KiB

Open AccessShort Note

4,5-Dimethylfuro[3,4-d]pyridazin-1(2H)-one

by Kirill A. Gomonov, Vasilii V. Pelipko, Igor A. Litvinov, Ruslan I. Baichurin and Sergey V. Makarenko

Molbank 2024, 2024(1), M1776; https://doi.org/10.3390/M1776 - 20 Feb 2024

Viewed by 2621

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. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 1027 KiB

Open AccessShort Note

N-(2,2-Diphenylethyl)-4-nitrobenzamide

by Diyana Dimitrova, Stanimir Manolov, Iliyan Ivanov, Dimitar Bojilov, Lyusi Kasamova and Paraskev Nedialkov

Molbank 2024, 2024(1), M1775; https://doi.org/10.3390/M1775 - 12 Feb 2024

Viewed by 2367

Abstract

In this study, we outline the eco-friendly mechanosynthesis of N-(2,2-diphenylethyl)-4-nitrobenzamide by reacting 2,2-diphenylethan-1-amine with 4-nitrobenzoyl chloride. The resulting bio-functional hybrid compound was meticulously characterized through the analysis of ¹H-, ¹³C-NMR, UV, and detailed mass spectral analysis. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 1964 KiB

Open AccessShort Note

2-Benzoyl-4-phenyl-1,2,5-thiadiazol-3(2H)-one 1,1-Dioxide

by Emmanouil Broumidis, Samuel B. H. Patterson, Georgina M. Rosair, Panayiotis A. Koutentis and Andreas S. Kalogirou

Molbank 2024, 2024(1), M1774; https://doi.org/10.3390/M1774 - 12 Feb 2024

Viewed by 1585

Abstract

3,5-Diphenyl-4H-1,2,6-thiadiazin-4-one treated with meta-chloroperoxybenzoic acid undergoes an oxidative ring contraction to give 2-benzoyl-4-phenyl-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide in a 29% yield, the structure of which is supported by single-crystal X-ray diffraction analysis and the available spectroscopic data. Full article

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

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5 pages, 392 KiB

Open AccessCommunication

Four-Step Synthesis of 3-Allyl-2-(allyloxy)-5-bromoaniline from 2-Allylphenol

by Enrique B. Aparicio, Stephen R. Isbel and Alejandro Bugarin

Molbank 2024, 2024(1), M1773; https://doi.org/10.3390/M1773 - 7 Feb 2024

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Abstract

This communication reports a four-step protocol to produce 3-allyl-2-(allyloxy)-5-bromoaniline 5 from commercially available 2-allylphenol. The synthetic steps used were nitration, selective bromination, allylation, and reduction of the nitro group. Full article

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9 pages, 2545 KiB

Open AccessCommunication

Synthesis and Anti-Inflammatory Activity of (Z)-4-(2-(3-Oxopiperazin-2-ylidene)acetyl)benzoic Acid

by Maksim V. Dmitriev, Ekaterina E. Khramtsova, Danila Y. Apuskin, Alexander I. Andreev, Ilya I. Kovalenko, Irina V. Mashevskaya and Andrey N. Maslivets

Molbank 2024, 2024(1), M1772; https://doi.org/10.3390/M1772 - 5 Feb 2024

Cited by 1 | Viewed by 1606

Abstract

Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of [...] Read more.

Non-steroidal anti-inflammatory drugs (NSAIDs) are an important class of medications; however, they have some drawbacks. We are developing a new NSAID with pronounced anti-inflammatory and analgesic activities and a very low toxicity—(Z)-3-(2-oxo-2-(p-tolyl)ethylidene)piperazin-2-one (piron). In this work, we describe the synthesis of the main metabolite of piron—(Z)-4-(2-(3-oxopiperazin-2-ylidene)acetyl)benzoic acid. The anti-inflammatory activity of the synthesized metabolite was determined in vivo. Full article

(This article belongs to the Collection Heterocycle Reactions)

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7 pages, 2421 KiB

Open AccessShort Note

N-(2,4-Difluorophenyl)-2-fluorobenzamide

by Niall Hehir and John F. Gallagher

Molbank 2024, 2024(1), M1771; https://doi.org/10.3390/M1771 - 4 Feb 2024

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Abstract

The title compound N-(2,4-difluorophenyl)-2-fluorobenzamide (Fo24) was synthesized in high yield (1.09 g; 87%) using standard synthetic procedures from the condensation reaction of 2-fluorobenzoyl chloride with 2,4-difluoroaniline. Crystals of Fo24 were grown from CH₂Cl₂ at room temperature. The [...] Read more.

The title compound N-(2,4-difluorophenyl)-2-fluorobenzamide (Fo24) was synthesized in high yield (1.09 g; 87%) using standard synthetic procedures from the condensation reaction of 2-fluorobenzoyl chloride with 2,4-difluoroaniline. Crystals of Fo24 were grown from CH₂Cl₂ at room temperature. The Fo24 crystal structure was determined using single-crystal X-ray diffraction methods at 294 (1) K in space group Pn (No. 7). Fo24 is the second regular tri-fluorinated benzamide with the formula C₁₃H₈F₃N₁O₁ to be reported and contrasts with the more common difluorinated and tetra-fluorinated analogues. In Fo24, both aromatic rings are effectively coplanar with an interplanar angle of 0.7(2)°. The central amide group plane is oriented by 23.04(18)° and 23.69(17)° from both aromatic rings, forming an intramolecular contact with an ortho-F12 atom with H1⋯F12 = 2.12(4) Å. The primary hydrogen bonds are 1D amide–amide interactions that form along the b-axis direction. In addition, weaker C-H⋯F/O interactions are noted: a R²₂(12) synthon involving two C-H, a N-H and two C-F groups, with C-F⋯C ring–ring stacking contacts completing the interactions. Full article

(This article belongs to the Section Structure Determination)

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7 pages, 651 KiB

Open AccessCommunication

Chlorido-pentamethylcyclopentadienyl-[2-(2-pyridyl-кN)-ferrocenyl-кC]-iridium(III)

by Stefan Weigand and Karlheinz Sünkel

Molbank 2024, 2024(1), M1770; https://doi.org/10.3390/M1770 - 2 Feb 2024

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Abstract

Treatment of 2-pyridyl-ferrocene wit [Cp*IrCl₂]₂ in the presence of NaOAc produces the title compound Cp*ClIr[(C₅H₃C₅H₄N-кN,кC)Fe(C₅H₅)] (2) in low yield. A crystal structure determination shows the (S_pS_Ir/R_pR_Ir)-2 enantiomeric pair of diastereomers. Full article

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6 pages, 1447 KiB

Open AccessShort Note

(E)-5-[Bromo(phenyl)methylene]-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole

by Nobuyoshi Morita, Saki Kurami, Naho Ishii, Kosaku Tanaka III, Yoshimitsu Hashimoto and Osamu Tamura

Molbank 2024, 2024(1), M1769; https://doi.org/10.3390/M1769 - 2 Feb 2024

Viewed by 1468

Abstract

One-pot synthesis of (E)-5-[bromo(phenyl)methylene]-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (9) from propargylic alcohol 5 and p-toluamide (6) was achieved via gold(III)-catalyzed propargylic substitution, followed by gold(III)-catalyzed bromocyclization. The structure of 9 was confirmed by an X-ray crystallographic analysis. Full article

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

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5 pages, 341 KiB

Open AccessShort Note

9-Vinyl-9H-carbazole-3,6-dicarbonitrile

by Kristina Svetlova, Alexander Kazantsev, Oleg Levin, Sofia Filippova and Elena Alekseeva

Molbank 2024, 2024(1), M1768; https://doi.org/10.3390/M1768 - 2 Feb 2024

Viewed by 1685

Abstract

Carbazole polymers attract significant attention as promising luminophores, organic electronic and photovoltaic materials, photo/electrocatalysts, energy storage materials, redox mediators and catalysts. However, the oxidation potential of the commercially available poly(vinylcarbazole) is insufficient for some applications such as high-voltage Li-Ion batteries. We have proposed [...] Read more.

Carbazole polymers attract significant attention as promising luminophores, organic electronic and photovoltaic materials, photo/electrocatalysts, energy storage materials, redox mediators and catalysts. However, the oxidation potential of the commercially available poly(vinylcarbazole) is insufficient for some applications such as high-voltage Li-Ion batteries. We have proposed a monomer for the novel polycarbazole with an increased oxidation potential, which will be compatible with high-voltage cathode materials for Li-Ion. In addition, the proposed polymer is an interesting substrate for the further carbonization to obtain N-doped carbons with a high electrocatalytic activity level. Full article

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5 pages, 887 KiB

Open AccessCommunication

Synthesis of a Novel Tetracyclic Isoxazole by Intramolecular Nitrile Oxide Cycloaddition

by Gavin R. Hoffman and Allen M. Schoffstall

Molbank 2024, 2024(1), M1767; https://doi.org/10.3390/M1767 - 1 Feb 2024

Cited by 1 | Viewed by 1587

Abstract

Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an N-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing [...] Read more.

Intramolecular cycloadditions have the great advantage of forming two rings simultaneously. We report the use of intramolecular [3 + 2] cycloaddition of the nitrile oxide derived from an N-propargylbenzimidazole oxime in the synthesis of a hitherto unreported tetracyclic isoxazole-containing ring system bearing “6-5-5-5”-membered ring fusions. The initial condensation was achieved through reaction of o-phenylenediamine with ethyl diethoxyacetate, followed by alkylation with propargyl bromide, deprotection of the acetal to the aldehyde, formation of an aldoxime, and intramolecular nitrile oxide cycloaddition (INOC). Characterization of the aldoxime and tetracyclic isoxazole is included herein. Full article

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Molbank, Volume 2024, Issue 1 (March 2024) – 45 articles

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