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Molbank
Volume 2024
Issue 4
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Molbank, Volume 2024, Issue 4 (December 2024) – 58 articles

Cover Story (view full-size image): The biomass derivative levoglucosenone and its reduced form Cyrene, which are obtained from the acid-catalyzed pyrolysis of cellulose, have emerged as promising chiral platform chemicals in materials chemistry and building blocks for the production of pharmaceuticals or natural products. Reports of fluorinated derivatives are limited; however, the incorporation of fluorine could be beneficial for the enantioselective synthesis of pharmaceuticals and natural products. We report a one-carbon difluorocyclopropanation/ring-expansion of Cyrene. The ring-enlargement was achieved by converting Cyrene into an enamine, reacting it with an in situ generated difluorocarbene, and then heating to open the cyclopropane ring. Access to the product provides access to a novel fluorinated analogue of this important chiral biomass pyrolysis product. View this paper
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4 pages, 759 KiB  
Short Note
Bis(1,1,1,3,3,3-hexafluoropropan-2-yl) [1,1′-biphenyl]-4,4′-dicarboxylate
by Ethan T. Mercier, Manisha Sharma, Adam M. Graichen and Nicholas E. Leadbeater
Molbank 2024, 2024(4), M1943; https://doi.org/10.3390/M1943 - 20 Dec 2024
Viewed by 509
Abstract
The oxidative esterification of 4,4′-Biphenyldicarboxaldehyde with hexafluoroisopropanol is reported. The methodology, making a novel hexafluoroisopropyl ester uses a green, recyclable oxoammonium salt along with easily obtained sodium persulfate. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

4 pages, 575 KiB  
Short Note
6-Amino-7-((4-methoxybenzyl)thio)quinazolin-4(3H)-one
by Susila Thapa and Jeanne L. Bolliger
Molbank 2024, 2024(4), M1942; https://doi.org/10.3390/M1942 - 19 Dec 2024
Viewed by 508
Abstract
The titular compound, 6-amino-7-((4-methoxybenzyl)thio)quinazolin-4(3H)-one, was prepared from 7-fluoro-6-nitroquinazolin-4(3H)-one via a nucleophilic aromatic substitution reaction followed by a reduction of the nitro group. Characterization of the target compound via 1H NMR, 13C NMR, and HRMS confirmed its structure. Full article
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Graphical abstract

3 pages, 360 KiB  
Short Note
5-Bromo-N′-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide
by Nur Pasca Aijijiyah, Arif Fadlan, Sri Ningsih and Mardi Santoso
Molbank 2024, 2024(4), M1941; https://doi.org/10.3390/M1941 - 19 Dec 2024
Viewed by 519
Abstract
5-Bromo-N′-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide (1) was successfully synthesized in 79.4% yield by reaction of isatin with 5-bromofuran-2-carbohydrazide in acidic conditions under reflux. The structure of synthesized compound 1 was confirmed by 1H and 13C NMR, FTIR, and HRMS spectrometers. It [...] Read more.
5-Bromo-N′-(2-oxoindolin-3-ylidene)furan-2-carbohydrazide (1) was successfully synthesized in 79.4% yield by reaction of isatin with 5-bromofuran-2-carbohydrazide in acidic conditions under reflux. The structure of synthesized compound 1 was confirmed by 1H and 13C NMR, FTIR, and HRMS spectrometers. It is necessary to evaluate compound 1 as an anti-inflammatory agent. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Scheme 1

8 pages, 1246 KiB  
Short Note
3-(4-Ferrocenyl-1H-1,2,3-triazol-1-yl)cholic Acid
by Valeria D’Annibale, Venanzio Raglione, Francesco Lisi, Elisa Verdirosi, Lorenza Romagnoli, Danilo Dini, Luciano Galantini and Andrea D’Annibale
Molbank 2024, 2024(4), M1940; https://doi.org/10.3390/M1940 - 19 Dec 2024
Viewed by 540
Abstract
Surfactants are very important compounds that are ubiquitous in biological systems and detergents. Among them, ferrocene surfactants are a very valuable class of stimuli-responsive materials since the presence of ferrocene moiety discloses the chance to control and even modify their amphiphilic properties via [...] Read more.
Surfactants are very important compounds that are ubiquitous in biological systems and detergents. Among them, ferrocene surfactants are a very valuable class of stimuli-responsive materials since the presence of ferrocene moiety discloses the chance to control and even modify their amphiphilic properties via a redox-induced change in the surfactant charge. In this paper, we report a new ferrocene-based surfactant: a ferrocene C-3 derivative of cholic acid, a non-classical surfactant. The title compound of this work was meant to show the significant self-assembly behaviour typical of bile salts, improved by the presence of the aromatic ferrocene subunit. We intended to demonstrate that the presence of the redox mediator should provide the derivative with sensitivity to an oxidative stimulus and control over the aggregation properties. The title compound was prepared in two steps from easily accessible precursors, and its optical properties were investigated through UV-Vis absorption spectroscopy. The determination of its critical micellar concentration and redox potential confirmed this derivative’s amphiphilic nature and its tendency to be reversibly oxidized. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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6 pages, 1541 KiB  
Communication
Ethyl 4H-Pyran-4-one-2-carboxylate
by R. Alan Aitken, Alexander J. B. Nelson and Alexandra M. Z. Slawin
Molbank 2024, 2024(4), M1939; https://doi.org/10.3390/M1939 - 16 Dec 2024
Viewed by 697
Abstract
The title compound was characterised for the first time by 13C NMR, including the determination of CH coupling constants, and its X-ray structure was determined, showing double ribbons of molecules in the crystal held together by weak CH to O=C hydrogen bonds. Full article
(This article belongs to the Section Structure Determination)
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5 pages, 836 KiB  
Short Note
(E)-1-(Benzo[d][1,3]dioxol-5-yl)-5,6,6-trimethylhept-4-en-3-one
by Mario Rico-Molina, Joaquín Altarejos and Sofía Salido
Molbank 2024, 2024(4), M1938; https://doi.org/10.3390/M1938 (registering DOI) - 11 Dec 2024
Viewed by 650 | Correction
Abstract
The title compound (1) was obtained within a project to synthesize analogs of the antiepileptic drug stiripentol. Compound 1 was synthesized by aldol addition of the lithium enolate of 4-(benzo[d][1,3]dioxol-5-yl)butan-2-one (2) to 3,3-dimethylbutan-2-one (3), followed [...] Read more.
The title compound (1) was obtained within a project to synthesize analogs of the antiepileptic drug stiripentol. Compound 1 was synthesized by aldol addition of the lithium enolate of 4-(benzo[d][1,3]dioxol-5-yl)butan-2-one (2) to 3,3-dimethylbutan-2-one (3), followed by the dehydration of the resulting β-hydroxy-ketone under acid processing. The structure of 1 was established by 1D and 2D NMR spectroscopy and high-resolution mass spectrometry. Full article
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5 pages, 927 KiB  
Short Note
5,10-Diiododibenzo[a,e]pentalene
by Natsumi Ohara, Chinatsu Ogiwara and Takuya Kuwabara
Molbank 2024, 2024(4), M1937; https://doi.org/10.3390/M1937 - 10 Dec 2024
Viewed by 527
Abstract
The crystal structure and the improved synthesis of the title compound (1) are presented. Treatment of 5,10-disilyldibenzo[a,e]pentalenes (2a and 2b) with iodine chloride (ICl) readily provided 1 in good yields. Recrystallization from a dichloromethane/hexane solution [...] Read more.
The crystal structure and the improved synthesis of the title compound (1) are presented. Treatment of 5,10-disilyldibenzo[a,e]pentalenes (2a and 2b) with iodine chloride (ICl) readily provided 1 in good yields. Recrystallization from a dichloromethane/hexane solution afforded single crystals suitable for X-ray diffraction studies. In the packing structure, iodine···iodine interactions classified as type II halogen bonding were found, forming the zigzag I…I chains along the ac-plane. Full article
(This article belongs to the Section Structure Determination)
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6 pages, 1240 KiB  
Communication
Synthesis of (5Z)-3-Allyl-5-{[5-(4-methoxyphenyl)thiophen-2-yl]methylidene}-2-sulfanylidene-1,3-thiazolidin-4-one in L-Proline-Based Deep Eutectic Solvent
by Stéphanie Hesse, Isabelle Jourdain, Abderrahim Khatyr and Michael Knorr
Molbank 2024, 2024(4), M1936; https://doi.org/10.3390/M1936 - 10 Dec 2024
Viewed by 511
Abstract
3-N-allylrhodanine was condensed with 5-(4-methoxyphenyl)-thiophene-2-carbaldehyde in an L-proline-based deep eutectic solvent (DES) to obtain the π-conjugated heterocyclic rhodanine compound (5Z)-3-allyl-5-{[5-(4-methoxyphenyl)thiophen-2-yl]methylidene}-2-sulfanylidene-1,3-thiazolidin-4-one (2). Compound 2 was characterized by NMR spectroscopy, and its UV-vis spectrum was compared with that of [...] Read more.
3-N-allylrhodanine was condensed with 5-(4-methoxyphenyl)-thiophene-2-carbaldehyde in an L-proline-based deep eutectic solvent (DES) to obtain the π-conjugated heterocyclic rhodanine compound (5Z)-3-allyl-5-{[5-(4-methoxyphenyl)thiophen-2-yl]methylidene}-2-sulfanylidene-1,3-thiazolidin-4-one (2). Compound 2 was characterized by NMR spectroscopy, and its UV-vis spectrum was compared with that of the related derivative 3-allyl-5-(4-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one (1). Preliminary results revealed that compound 2 is emissive at room temperature in solution. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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6 pages, 809 KiB  
Communication
17β-Hydroxy-2-oxa-5α-androstan-3-one
by Savina Stoyanova, Georgi Dinkov and Milen G. Bogdanov
Molbank 2024, 2024(4), M1935; https://doi.org/10.3390/M1935 - 9 Dec 2024
Viewed by 905
Abstract
We have successfully synthesized a 2-oxa androstane derivative, 17β-hydroxy-2-oxa-5α-androstan-3-one (6), and confirmed its structure using NMR spectroscopy and mass spectrometry. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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12 pages, 3610 KiB  
Communication
Synthesis and Characterization of Hydrazine Bridge Cyclotriphosphazene Derivatives with Amide–Schiff Base Linkages Attached to Decyl and Hydroxy Terminal Groups
by Fatin Junaidah Mohamad Fazli and Zuhair Jamain
Molbank 2024, 2024(4), M1934; https://doi.org/10.3390/M1934 - 7 Dec 2024
Viewed by 986
Abstract
New cyclotriphosphazene derivatives featuring amide–Schiff base linkages with a hydrazine bridge and different terminal ends, such as decyl alkyl chains and hydroxy groups, were successfully synthesized and characterized. Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (NMR), and CHN elemental analysis were used [...] Read more.
New cyclotriphosphazene derivatives featuring amide–Schiff base linkages with a hydrazine bridge and different terminal ends, such as decyl alkyl chains and hydroxy groups, were successfully synthesized and characterized. Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (NMR), and CHN elemental analysis were used to characterize the structures of these compounds. The formation of hydrazine-bridged cyclotriphosphazene derivatives with amide–Schiff base linkages was confirmed by the FTIR spectra, showing a primary amine band for the amide linkage around ~3300 cm−1 and a band for the Schiff base linkage near ~1595 cm−1. This was further supported by NMR analysis, which displayed an amide proton (H-N-C=O) at ~δ 10.00 ppm and an azomethine proton (H-C=N) within the δ 8.40–8.70 ppm range. The 31P NMR spectra of cyclotriphosphazene compounds display a singlet at ~δ 8.20 ppm, indicating an upfield shift that suggests the complete substitution of all phosphorus atoms with identical side chains. Furthermore, CHN analysis verified the purity of the synthesized compounds, with a percentage error below 2%. The introduction of hydrazine bridges and amide–Schiff base linkages into the cyclotriphosphazene core significantly enriches the molecular structure with diverse functional groups. These modifications not only improve the compound’s stability and reactivity, but also expand its potential for a wide range of applications. Full article
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6 pages, 851 KiB  
Communication
Cyclization Modes in Anilides of N-Protected 3-Oxo-4-phenylaminobutyric Acid Under Knorr Conditions
by Plamen Angelov and Yordanka Mollova-Sapundzhieva
Molbank 2024, 2024(4), M1933; https://doi.org/10.3390/M1933 - 6 Dec 2024
Viewed by 503
Abstract
Anilides of 3-oxo-4-phenylaminobutyric acid with Troc or COOEt protection at the phenylamino group undergo competing cyclization processes in neat polyphosphoric acid at 80 °C. Depending on the protecting group and the duration of the process, three main products in different ratios are formed. [...] Read more.
Anilides of 3-oxo-4-phenylaminobutyric acid with Troc or COOEt protection at the phenylamino group undergo competing cyclization processes in neat polyphosphoric acid at 80 °C. Depending on the protecting group and the duration of the process, three main products in different ratios are formed. Along with the quinolin-2-ones, resulting from the classic Knorr cyclization, an indole derivative and a spirocyclic product have also been obtained from the COOEt-protected substrate. It has been demonstrated that the obtained indole derivative is capable of further dearomative spirocyclization under the studied conditions. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Scheme 1

7 pages, 1507 KiB  
Short Note
1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane
by Jérémy Forté, Patrick Herson and Pascal Pigeon
Molbank 2024, 2024(4), M1932; https://doi.org/10.3390/M1932 - 6 Dec 2024
Viewed by 534
Abstract
Ferrociphenols are anticancer organometallic molecules bearing a ferrocene group linked, at least, to one para-phenol moiety via a double bond. Up to the present, their biological activity has been thought to be linked to their oxidation within cells to form a reactive [...] Read more.
Ferrociphenols are anticancer organometallic molecules bearing a ferrocene group linked, at least, to one para-phenol moiety via a double bond. Up to the present, their biological activity has been thought to be linked to their oxidation within cells to form a reactive quinone-methide metabolite with the participation of this central double bond. To prove this assertion, the alkenyl entity of ferrociphenol 1a (1,1-bis-(4-hydroxyphenyl)-2-ferrocenylbut-1-ene) was reduced by triethylsilane in an acidic medium to obtain the alkyl counterpart 1,1-bis(4-hydrophenyl)-2-ferrocenylbutane. 1,1-bis(4-hydrophenyl)-2-ferrocenylbutane was fully characterized by 1H NMR (including COSY), 13C NMR, HRMS, IR, elemental analysis and X-ray diffraction (XRD). Although missing the central double bond, this compound remains biologically active, opening the way to a new family of anticancer ferrocene-containing molecules. Full article
(This article belongs to the Section Structure Determination)
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4 pages, 903 KiB  
Short Note
2-((3R,9bS)-5,5-Dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one
by Yeongju Kim and Sung-Gon Kim
Molbank 2024, 2024(4), M1931; https://doi.org/10.3390/M1931 - 5 Dec 2024
Viewed by 523
Abstract
A highly efficient method has been developed for preparing 2-((3R,9bS)-5,5-dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one. This enantioenriched title compound was obtained via an organocatalytic asymmetric [3+2]-cycloaddition of benzo[d]isothiazole 1,1-dioxide with (E)-4-hydroxy-1-phenylbut-2-en-1-one, using a bifunctional squaramide-based chiral [...] Read more.
A highly efficient method has been developed for preparing 2-((3R,9bS)-5,5-dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one. This enantioenriched title compound was obtained via an organocatalytic asymmetric [3+2]-cycloaddition of benzo[d]isothiazole 1,1-dioxide with (E)-4-hydroxy-1-phenylbut-2-en-1-one, using a bifunctional squaramide-based chiral catalyst. The reaction yielded 99% of the product with high enantioselectivity and diastereoselectivity (89:11 er and >20:1 dr). The structure of the newly synthesized compound was confirmed by 1H-, 13C-NMR, IR and mass spectral data. Full article
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4 pages, 1292 KiB  
Short Note
4-(Benzoxazol-2-yl)phenyl 3-((3-Chloro-1,4-Naphthoquinon-2-yl)amino)phenyl Sulfate
by Nadezhda V. Danilenko, Mariia O. Lutsuk and Andrei I. Khlebnikov
Molbank 2024, 2024(4), M1930; https://doi.org/10.3390/M1930 - 5 Dec 2024
Viewed by 484
Abstract
New 4-(benzoxazol-2-yl)phenyl 3-((3-chloro-1,4-naphthoquinon-2-yl)amino)phenyl sulfate was synthesized via the SuFEx click reaction between fluorosulfate-containing 1,4-naphthoquinone and 2-(4-hydroxyphenyl)benzoxazole. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was used as an organic base, while triethylamine was inactive in this reaction. Full article
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5 pages, 788 KiB  
Communication
Fluorination Homologation of Biorenewable Synthon Cyrene
by Johannes Puschnig and Ben W. Greatrex
Molbank 2024, 2024(4), M1929; https://doi.org/10.3390/M1929 - 5 Dec 2024
Viewed by 484
Abstract
A one-carbon difluorocyclopropanation/ring-expansion has been developed for the chiral synthon Cyrene, which is obtained via cellulose pyrolysis. The ring-enlargement was achieved by converting Cyrene (dihydrolevoglucosenone) into an enamine, reacting it with an in situ-generated difluorocarbene, and then heating it to ring-open the cyclopropane. [...] Read more.
A one-carbon difluorocyclopropanation/ring-expansion has been developed for the chiral synthon Cyrene, which is obtained via cellulose pyrolysis. The ring-enlargement was achieved by converting Cyrene (dihydrolevoglucosenone) into an enamine, reacting it with an in situ-generated difluorocarbene, and then heating it to ring-open the cyclopropane. Access to the product provides access to fluorinated analogues of this valuable chiral biomass derivative. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

14 pages, 13839 KiB  
Communication
Crystal Structures of 9,9-Disubstituted Fluorene Derivatives Bearing Methyl, Hydroxymethyl or Pyridinylmethyl Groups
by Thomas Hanauer, Pierre Seidel, Wilhelm Seichter and Monika Mazik
Molbank 2024, 2024(4), M1928; https://doi.org/10.3390/M1928 - 3 Dec 2024
Viewed by 873
Abstract
The wide range of application possibilities of fluorene derivatives, due to their unique physical and chemical properties, has made this class of molecules important for various disciplines. The synthesis of these compounds and the study of their properties are, therefore, of great scientific [...] Read more.
The wide range of application possibilities of fluorene derivatives, due to their unique physical and chemical properties, has made this class of molecules important for various disciplines. The synthesis of these compounds and the study of their properties are, therefore, of great scientific interest. Due to their reactivity and sensitivity to oxidation, the 9-position of the fluorene skeleton is often double substituted, for example, to ensure the long-term stability of materials. Single crystal structure analysis, among other methods, plays a very important role in the development of various fluorene-based systems. In this paper, the crystal structures of three 9,9-disubstituted fluorene derivatives bearing methyl, hydroxymethyl or pyridinylmethyl groups are described (three solvent-free structures and one toluene solvate). A detailed evaluation of the intermolecular interactions, supported by Hirshfeld surface analysis, is the subject of this article. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

6 pages, 1298 KiB  
Short Note
2-([1,1′-Biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3,3-dimethyl-3H-indole
by Gabrielė Varvuolytė, Aurimas Bieliauskas, Neringa Kleizienė, Asta Žukauskaitė and Algirdas Šačkus
Molbank 2024, 2024(4), M1927; https://doi.org/10.3390/M1927 - 28 Nov 2024
Viewed by 610
Abstract
The ligandless palladium-catalyzed Heck reaction of 4-ethenyl-3-methoxy-1-phenyl-1H-pyrazole and 2-([1,1′-biphenyl]-4-yl)-5-bromo-3,3-dimethyl-3H-indole gave the previously unreported 2-([1,1′-biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3,3-dimethyl-3H-indole in 45% yield. The compound was characterized using NMR, FT-IR spectroscopy, and HRMS data. The optical properties of the [...] Read more.
The ligandless palladium-catalyzed Heck reaction of 4-ethenyl-3-methoxy-1-phenyl-1H-pyrazole and 2-([1,1′-biphenyl]-4-yl)-5-bromo-3,3-dimethyl-3H-indole gave the previously unreported 2-([1,1′-biphenyl]-4-yl)-5-[(E)-2-(3-methoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-3,3-dimethyl-3H-indole in 45% yield. The compound was characterized using NMR, FT-IR spectroscopy, and HRMS data. The optical properties of the compound were investigated in tetrahydrofuran by UV-Vis and fluorescence spectroscopy. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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10 pages, 3408 KiB  
Communication
Synthesis of N-p-Fluorothiosemicarbazone and of Bis(N-p-Fluorophenylthiourea): Crystal Structure and Conformational Analysis of N,N′-Bis(4-Fluorophenyl)Hydrazine-1,2-Bis(Carbothioamide)
by Sirine Salhi, Dorra Kanzari-Mnallah, Isabelle Jourdain, Michael Knorr, Carsten Strohmann, Jan-Lukas Kirchhoff, Hédi Mrabet and Azaiez Ben Akacha
Molbank 2024, 2024(4), M1926; https://doi.org/10.3390/M1926 - 28 Nov 2024
Viewed by 557
Abstract
The reaction of the phosphonated hydrazone (2-hydrazineylidenepropyl) diphenylphosphine oxide 1 with p-fluorophenyl-isothiocyanate yields as a major product the thiosemicarbazone Ph2P(=O)CH2{C=N-NH(C=S)-N(H)C6H4F}CH3 (2-(1-(diphenylphosphoryl)propan-2-ylidene)-N-(4-fluorophenyl)hydrazine-1-carbothioamide) 2 along with bis(N-p-fluorophenylthiourea) 3 as [...] Read more.
The reaction of the phosphonated hydrazone (2-hydrazineylidenepropyl) diphenylphosphine oxide 1 with p-fluorophenyl-isothiocyanate yields as a major product the thiosemicarbazone Ph2P(=O)CH2{C=N-NH(C=S)-N(H)C6H4F}CH3 (2-(1-(diphenylphosphoryl)propan-2-ylidene)-N-(4-fluorophenyl)hydrazine-1-carbothioamide) 2 along with bis(N-p-fluorophenylthiourea) 3 as a minor product. The latter compound 3 was isolated as the main product by direct treatment of p-FC6H4N=C=S with hydrazine in a 2:1 ratio. Both 2 and 3 were characterized by NMR. Furthermore, the molecular structure of 3 was elucidated by an X-ray diffraction study, revealing both intra- and intermolecular secondary interactions. A conformational DFT study, at the B3LYP/6-311 G++ (d, p) level of theory, confirms a good match between the calculated structure and the experimental one. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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5 pages, 913 KiB  
Communication
3-Methyl-2-(5-((trimethylsilyl)ethynyl)pyridin-2-yl)butan-2-ol
by Oleg A. Mikhailov, Almira R. Kurbangalieva and Ilya D. Gridnev
Molbank 2024, 2024(4), M1925; https://doi.org/10.3390/M1925 - 27 Nov 2024
Viewed by 444
Abstract
The reactions of dialkylzinc reagents with ketones are scarcely studied. In this paper, we describe a previously unknown direct alkylation of substituted 2-acetylpyridine with diisopropyl zinc, which gave a corresponding novel alcohol with 82% yield. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Scheme 1

7 pages, 1667 KiB  
Short Note
Ammonium Oxathioamidate
by M. Carla Aragoni, David B. Cordes, Anna Pintus, Enrico Podda, Riccardo Serra, Alexandra M. Z. Slawin, J. Derek Woollins and Massimiliano Arca
Molbank 2024, 2024(4), M1924; https://doi.org/10.3390/M1924 - 26 Nov 2024
Viewed by 621
Abstract
Ammonium oxathioamidate (1) was synthesised by the reaction between O-ethyl-thioxamate (oxalic acid-1-amide-2-O-ethyl ester) and ammonium hydrogen carbonate in water solution. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and [...] Read more.
Ammonium oxathioamidate (1) was synthesised by the reaction between O-ethyl-thioxamate (oxalic acid-1-amide-2-O-ethyl ester) and ammonium hydrogen carbonate in water solution. Compound 1 was fully characterised by both microanalytical (elemental analysis, melting point determination) and spectroscopic means (FT-IR and NMR spectroscopy). Crystals suitable for single-crystal X-ray diffraction were isolated by slow evaporation of an ethanol solution of the compound. The analysis of the crystal packing reveals the prominent role exerted by intermolecular hydrogen bonding (HB) and chalcogen bonding (ChB) interactions. Full article
(This article belongs to the Section Structure Determination)
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8 pages, 2827 KiB  
Communication
Coordination of O-Propyl-N-phenylthiocarbamate to HgI2 and the Crystallographic Characterization of an Anilinium Chloride Thiocarbamate Adduct
by Wafa Arar, Nuri Ekici, Michael Knorr, Isabelle Jourdain, Carsten Strohmann and Jan-Lukas Kirchhoff
Molbank 2024, 2024(4), M1923; https://doi.org/10.3390/M1923 - 22 Nov 2024
Viewed by 603
Abstract
In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, HgI2 was reacted with one equivalent of PrOC(=S)N(H)Ph L in toluene solution to afford the 1D polymeric title compound [{IHg(μ-I)}{κ1-PrOC(=S)N(H)Ph}]n CP1. The formation [...] Read more.
In order to investigate the coordination chemistry of O-alkyl N-aryl thiocarbamate ligands, HgI2 was reacted with one equivalent of PrOC(=S)N(H)Ph L in toluene solution to afford the 1D polymeric title compound [{IHg(μ-I)}{κ1-PrOC(=S)N(H)Ph}]n CP1. The formation of this iodide-bridged coordination polymer was ascertained by a single-crystal X-ray diffraction study performed at 100 K, as well as the formation of an adduct between anilinium chloride and L forming a supramolecular ribbon of composition [L(PhNH3)(Cl)]. The occurrence of anilinium chloride is due to the partial hydrolysis of L in the presence of HCl. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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8 pages, 2407 KiB  
Short Note
6,8-Dibromo-11H-indeno[1,2-b]quinolin-11-one
by Anastasia R. Kovrizhina, Dauren Tolegen, Dmitry I. Pavlov, Andrei S. Potapov and Andrei I. Khlebnikov
Molbank 2024, 2024(4), M1922; https://doi.org/10.3390/M1922 - 21 Nov 2024
Viewed by 464
Abstract
We report the synthesis of the new compound 6,8-dibromo-11H-indeno[1,2-b]quinolin-11-one, which presents an important type of nitrogen-containing heterocycles and is a useful intermediate product in organic synthesis. The structure of the compound was confirmed by the single crystal X-ray diffraction. [...] Read more.
We report the synthesis of the new compound 6,8-dibromo-11H-indeno[1,2-b]quinolin-11-one, which presents an important type of nitrogen-containing heterocycles and is a useful intermediate product in organic synthesis. The structure of the compound was confirmed by the single crystal X-ray diffraction. Molecular docking analysis revealed that 6,8-dibromo-11H-indeno[1,2-b]quinolin-11-one may effectively intercalate with DNA. The synthesized indenoquinoline derivative thus represents a promising lead compound for developing targeted anticancer and anti-inflammatory drugs. Full article
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5 pages, 824 KiB  
Short Note
Cyclo[Tri(thiomethyl-1,2-phenylmethylene)]
by Pablo Simón Marqués, Nicolas Bréfuel and Claire Kammerer
Molbank 2024, 2024(4), M1921; https://doi.org/10.3390/M1921 - 21 Nov 2024
Viewed by 480
Abstract
During the purification of a reported compound named 1,3-dihydrobenzo[c]thiophene, we isolated an unexpected molecule in one of the chromatography fractions by serendipity. Structural elucidation using common techniques such as 1D and 2D NMR, and mass spectrometry revealed the nature of this [...] Read more.
During the purification of a reported compound named 1,3-dihydrobenzo[c]thiophene, we isolated an unexpected molecule in one of the chromatography fractions by serendipity. Structural elucidation using common techniques such as 1D and 2D NMR, and mass spectrometry revealed the nature of this novel product characterized as cyclo[tri(thiomethyl-1,2-phenylmethylene)]. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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4 pages, 611 KiB  
Short Note
trans-11-(3,4-Dimethoxyphenyl)-2,3,8,9-tetramethoxy-6-oxo-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic Acid
by Victor Angelov, Savina Stoyanova and Milen G. Bogdanov
Molbank 2024, 2024(4), M1920; https://doi.org/10.3390/M1920 - 19 Nov 2024
Viewed by 1342
Abstract
The title compound, trans-11-(3,4-Dimethoxyphenyl)-2,3,8,9-tetramethoxy-6-oxo-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid (4), was synthesized for the first time via a two-step protocol from 3,4-dimethoxyhomophthalic anhydride (1) and 3,4-dimethoxybenzaldehyde (DMBA). In the first step, 1 reacts with DMBA to give [...] Read more.
The title compound, trans-11-(3,4-Dimethoxyphenyl)-2,3,8,9-tetramethoxy-6-oxo-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid (4), was synthesized for the first time via a two-step protocol from 3,4-dimethoxyhomophthalic anhydride (1) and 3,4-dimethoxybenzaldehyde (DMBA). In the first step, 1 reacts with DMBA to give trans-3-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-4-carboxylic acid (2), which further reacts with two additional equivalents of 1 to give 4. Compound 4 was characterized by means of spectral methods—1H-, 13C-, DEPT-135-NMR, and HRMS. Full article
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5 pages, 952 KiB  
Short Note
5,5’-Selenobis(1-benzyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde)
by Emeline Grosjean, Julien Rizet, Shekoufeh Arabi Aliabadi, Joelle Azéma-Despeyroux, Pascal Hoffmann and Christian Lherbet
Molbank 2024, 2024(4), M1919; https://doi.org/10.3390/M1919 - 18 Nov 2024
Viewed by 447
Abstract
Selenium compounds have garnered significant attention in the field of medicinal chemistry due to their unique biochemical properties and potential therapeutic applications for different pathologies. In this study, we report the synthesis of a new selenylated bis-pyridone compound using SeO2 as the [...] Read more.
Selenium compounds have garnered significant attention in the field of medicinal chemistry due to their unique biochemical properties and potential therapeutic applications for different pathologies. In this study, we report the synthesis of a new selenylated bis-pyridone compound using SeO2 as the source of selenium. Detailed 1H and 13C NMR characterizations and mass spectral analysis are given. Full article
(This article belongs to the Collection Heterocycle Reactions)
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8 pages, 651 KiB  
Communication
A Gram Scale Synthesis of 3,4-Dihalogen Substituted 1,8-Naphthalimides
by Denitsa Anastasova, Monika Mutovska, Natali Simeonova, Irena Zagranyarska, Zlatina Vlahova, Stanimir Stoyanov and Yulian Zagranyarski
Molbank 2024, 2024(4), M1918; https://doi.org/10.3390/M1918 - 18 Nov 2024
Viewed by 595
Abstract
A general protocol for the synthesis of 3,4-dihalogen substituted 1,8-naphthalimides is proposed, starting from available and cheap 1,8-naphthalic anhydride. The reported new compounds have only bromine or chlorine atoms as substituents, in contrast to the known iodo-containing analogues. This is an advantage in [...] Read more.
A general protocol for the synthesis of 3,4-dihalogen substituted 1,8-naphthalimides is proposed, starting from available and cheap 1,8-naphthalic anhydride. The reported new compounds have only bromine or chlorine atoms as substituents, in contrast to the known iodo-containing analogues. This is an advantage in possible aryl nucleophilic substitution or cross-coupling modifications, making them interesting and important building-block molecules in naphthalimide chemistry. Although the procedure includes five synthetic steps, they are quick and straightforward. The overall yields are relatively high (48–62%), and only one column of chromatographic purification is needed. All the reactions were carried out on a multigram scale to allow the target building-block compounds to be obtained in sufficient amounts for further derivatizations. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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6 pages, 1811 KiB  
Short Note
9,10-Bis(5H-dibenzo[b,f]azepino)anthracene
by Himeko Kawaguchi and Takuya Kuwabara
Molbank 2024, 2024(4), M1917; https://doi.org/10.3390/M1917 - 15 Nov 2024
Viewed by 618
Abstract
The title compound with a donor–π–donor (D–π–D) type triad structure was synthesized by Buchwald–Hartwig amination using 9,10-dibromoanthracene and 5H-dibenzo[b,f]azepine, and characterized by 1H, 13C{1H} NMR, HRMS, and X-ray diffraction analysis. The azepine–anthracene–azepine units [...] Read more.
The title compound with a donor–π–donor (D–π–D) type triad structure was synthesized by Buchwald–Hartwig amination using 9,10-dibromoanthracene and 5H-dibenzo[b,f]azepine, and characterized by 1H, 13C{1H} NMR, HRMS, and X-ray diffraction analysis. The azepine–anthracene–azepine units are nearly orthogonal to each other, with a torsion angle of 88°. A broad and weak absorption band around 410–480 nm and the low emission character (ΦF = 0.01) suggest the weak intramolecular charge transfer from the azepine to the anthracene unit due to the twisted structure. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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7 pages, 303 KiB  
Short Note
2,2′-[2,4-Bis(4-chlorophenyl)cyclobutane-1,3-diyl]bis(8-bromo-6-chloro-3-nitroimidazo[1,2-a]pyridine)
by Inès Jacquet, Romain Paoli-Lombardo, Caroline Castera-Ducros, Patrice Vanelle and Nicolas Primas
Molbank 2024, 2024(4), M1916; https://doi.org/10.3390/M1916 - 14 Nov 2024
Viewed by 632
Abstract
In the context of our ongoing studies on 3-nitroimidazo[1,2-a]pyridine derivatives as potent antileishmanial compounds, we isolated a new unexpected compound from the spontaneous cycloaddition of N-[2-(8-bromo-6-chloro-3-nitroimidazo[1,2-a]pyridin-2-yl)-1-(4-chlorophenyl)ethyl]-4-methylbenzenesulfonamide. The molecular structure was fully characterized by using 1H and 13C NMR, X-ray crystallography, and HRMS. Full article
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6 pages, 725 KiB  
Communication
Water-Mediated Synthesis of (E)-3-(1-Methyl-1H-benzo[d]imidazol-5-yl)-N-phenethylacrylamide, a Caffeic Acid Phenethyl Amide Analogue
by Muppidi Subbarao and Sean M. Kerwin
Molbank 2024, 2024(4), M1915; https://doi.org/10.3390/M1915 - 12 Nov 2024
Viewed by 619
Abstract
Caffeic acid phenethyl ester (CAPE) is a phenolic natural product with diverse biological activities, notably anticancer properties. However, its ester group is metabolically unstable. The amide derivative, CAPA, offers improved metabolic stability to esterases but still possesses a metabolically liable catechol group. In [...] Read more.
Caffeic acid phenethyl ester (CAPE) is a phenolic natural product with diverse biological activities, notably anticancer properties. However, its ester group is metabolically unstable. The amide derivative, CAPA, offers improved metabolic stability to esterases but still possesses a metabolically liable catechol group. In this work, we describe the synthesis of a novel CAPA analogue in which the catechol is replaced with a benzimidazole bioisostere via a water-mediated Wittig reaction. Full article
(This article belongs to the Section Natural Product Chemistry)
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9 pages, 1166 KiB  
Communication
One Pot Synthesis of New Powerful Building Blocks in 1,8-Naphthalimide Chemistry
by Monika Mutovska, Denitsa Anastasova, Natali Simeonova, Irena Zagranyarska, Zlatina Vlahova, Iva Ugrinova, Stanimir Stoyanov and Yulian Zagranyarski
Molbank 2024, 2024(4), M1914; https://doi.org/10.3390/M1914 - 11 Nov 2024
Viewed by 778
Abstract
This communication reports a reliable one-pot synthetic protocol for preparation on a multigram scale of 3-bromo- and 3,4-dibromo-6-nitro-1,8-naphthalic anhydride from commercially available and economical 1,8-naphthalic anhydride. The synthetic steps used were nitration and selective bromination in sulfuric acid at room temperature. The reaction [...] Read more.
This communication reports a reliable one-pot synthetic protocol for preparation on a multigram scale of 3-bromo- and 3,4-dibromo-6-nitro-1,8-naphthalic anhydride from commercially available and economical 1,8-naphthalic anhydride. The synthetic steps used were nitration and selective bromination in sulfuric acid at room temperature. The reaction takes place under mild conditions and is completely controllable depending on the equivalents of the brominating reagent used. Both anhydrides are powerful building blocks in naphthalimide chemistry. In addition, their imides and esters were also synthesized. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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