Molbank

8 pages, 1323 KB

Open AccessShort Note

N-(2-Fluoro-2-propen-1-yl)-5-(trifluoromethyl)-2-pyridinecarboxamide

by Taylor Semeniuk and Jean-Denys Hamel

Molbank 2025, 2025(4), M2078; https://doi.org/10.3390/M2078 - 21 Oct 2025

Herein, the synthesis and crystallization of the unreported compound N-(2-fluoro-2-propen-1-yl)-5-(trifluoromethyl)-2-pyridinecarboxamide is achieved via amide coupling with a (2-fluoroallyl)ammonium salt. The structural properties are analyzed via single-crystal X-ray crystallography. Hydrogen bonding interactions between the amide groups and pyridine nitrogen atoms create a unique [...] Read more.

Herein, the synthesis and crystallization of the unreported compound N-(2-fluoro-2-propen-1-yl)-5-(trifluoromethyl)-2-pyridinecarboxamide is achieved via amide coupling with a (2-fluoroallyl)ammonium salt. The structural properties are analyzed via single-crystal X-ray crystallography. Hydrogen bonding interactions between the amide groups and pyridine nitrogen atoms create a unique linear array of molecules in the crystal packing diagram. Furthermore, to validate the crystallographic data, the structural features of the compound are evaluated and compared to values reported in the literature. Full article

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7 pages, 1031 KB

Open AccessShort Note

2-Benzyl-6-carboxy-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-1-ium 2,2,2-trifluoroacetate

by Francesco Bavo, Christos Avgerinos, Elena Martino and Bente Frølund

Molbank 2025, 2025(4), M2077; https://doi.org/10.3390/M2077 - 20 Oct 2025

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Abstract

Cyclic guanidines are valuable scaffolds for the design of compounds acting on GABAergic neurotransmission, owing to their ability to mimic the amino functionality of GABA as bioisosteres. With the aim to obtain a more potent and selective betaine/GABA transporter (BGT1) inhibitor, a basic [...] Read more.

Cyclic guanidines are valuable scaffolds for the design of compounds acting on GABAergic neurotransmission, owing to their ability to mimic the amino functionality of GABA as bioisosteres. With the aim to obtain a more potent and selective betaine/GABA transporter (BGT1) inhibitor, a basic hydrolysis of ethyl (E)-2-(acetylimino)-1-(3-phenylprop-2-yn-1-yl)hexahydropyrimidine-5-carboxylate was attempted. However, we isolated a byproduct, which was identified as the trifluoroacetate salt of 2-benzyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-6-carboxylic acid. The structure was confirmed by NMR spectroscopy and LC-MS. Herein we report the preparation, characterization, and spectral data of this fused heterocyclic compound. Full article

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

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5 pages, 309 KB

Open AccessShort Note

1,1-Bis(4-ethylphenyl)-propan-1,2-diol

by Ichika Hayashida, Malokhat Uktamova, Sarvinoz Tirkasheva and Kohei Torikai

Molbank 2025, 2025(4), M2076; https://doi.org/10.3390/M2076 - 16 Oct 2025

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Abstract

Diols represent a structurally diverse class of compounds with considerable biological and functional significance. Herein, we describe the synthesis of 1,1-bis(4-ethylphenyl)propan-1,2-diol (BEPP) via a Grignard reaction. The structure of BEPP was unambiguously elucidated by ¹H and ¹³C nuclear magnetic resonance (NMR), [...] Read more.

Diols represent a structurally diverse class of compounds with considerable biological and functional significance. Herein, we describe the synthesis of 1,1-bis(4-ethylphenyl)propan-1,2-diol (BEPP) via a Grignard reaction. The structure of BEPP was unambiguously elucidated by ¹H and ¹³C nuclear magnetic resonance (NMR), heteronuclear multiple-bond correlation (HMBC), high-resolution mass spectrometry (HRMS), and infrared (IR) spectroscopy. Full article

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

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9 pages, 1163 KB

Open AccessShort Note

3-((Benzyloxy)carbonyl)bicyclo[1.1.1]pentane-1-carboxylic Acid

by Dennis D. Toporkov, Stacie K. Nelson, Jean-Denys Hamel and René T. Boeré

Molbank 2025, 2025(4), M2075; https://doi.org/10.3390/M2075 - 16 Oct 2025

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Abstract

The compound 3-((benzyloxy)carbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid was successfully synthesized. High-quality crystals were obtained, and its X-ray structure was solved and refined by Hirshfeld atom refinement using custom aspherical scattering factors with the Olex2/NoSphereA2 package. Hydrogen bonding interactions lead to head-to-head carboxylic acid dimer formation. A [...] Read more.

The compound 3-((benzyloxy)carbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid was successfully synthesized. High-quality crystals were obtained, and its X-ray structure was solved and refined by Hirshfeld atom refinement using custom aspherical scattering factors with the Olex2/NoSphereA2 package. Hydrogen bonding interactions lead to head-to-head carboxylic acid dimer formation. A positional disorder for the bridging H-atom was detected and modeled to two parts in a 0.85:0.15 ratio. Detailed comparison with a neutron diffraction study of benzoic acid at the same temperature (100 K) demonstrates that the E–H-bond distances in the title compound are in excellent agreement (differing less than 1%) and the displacement ellipsoids volumes to the model are also in excellent agreement to the neutron diffraction structure. Moreover, both the variation in refined disorder occupancy and differences in C=O and C–O lengths of the disordered carboxylic acids in the two structures track well with their dimer O···O separations. This is longer by 0.023 Å in the structure of the title compound than in that of benzoic acid. A database search was conducted and used for comparison of the title compound to other high-quality structures of bicyclo[1.1.1]pentane-containing species. Full article

(This article belongs to the Section Structure Determination)

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11 pages, 516 KB

Open AccessCommunication

Efficient Synthesis of Unsymmetrical 7,7′-Biindolizines

by Roxana Ciorteanu, Andreea Danila, Catalina Ionica Ciobanu, Ioana Radu, Ionel I. Mangalagiu and Ramona Danac

Molbank 2025, 2025(4), M2074; https://doi.org/10.3390/M2074 - 15 Oct 2025

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Abstract

Six new unsymmetrical 7,7′-biindolizines were synthesized through an efficient metal-free [2+2+1] cycloaddition of ethyl 3-benzoyl-7-(pyridin-4-yl)indolizine-1-carboxylate with two equivalents of dimethyl acetylenedicarboxylate in methanol. The transformation involves one C≡C triple bond cleavage and provides access to previously unexplored unsymmetrical functionalized 7,7′-biindolizines. Full article

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5 pages, 377 KB

Open AccessShort Note

(5R*,6R*) 11-Benzoyl-4,10-dimethyl-2,8-diphenyl-2,3,8,9-tetraazadispiro [4.0.4⁶.1⁵]undeca-3,9-diene-1,7-dione

by Michail N. Elinson, Varvara M. Kalashnikova, Yuliya E. Ryzhkova and Oleg A. Rakitin

Molbank 2025, 2025(4), M2073; https://doi.org/10.3390/M2073 - 15 Oct 2025

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Abstract

Cyclopropanes are important in drug discovery because their unique structure, including inherent three-dimensionality, can enhance a drug’s properties, such as metabolic stability, target binding, and membrane permeability. In this communication, (5R*,6R*) 11-benzoyl-4,10-dimethyl-2,8-diphenyl-2,3,8,9-tetraazadispiro[4.0.4⁶.1⁵]undeca-3,9-diene-1,7-dione was prepared via [...] Read more.

Cyclopropanes are important in drug discovery because their unique structure, including inherent three-dimensionality, can enhance a drug’s properties, such as metabolic stability, target binding, and membrane permeability. In this communication, (5R*,6R*) 11-benzoyl-4,10-dimethyl-2,8-diphenyl-2,3,8,9-tetraazadispiro[4.0.4⁶.1⁵]undeca-3,9-diene-1,7-dione was prepared via a stereoselective one-pot reaction of phenylglyoxal hydrate with two equivalents of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one in EtOH in the presence of sodium acetate and N-bromosuccinimide. The structure of the newly synthesized compound was established by ¹H and ¹³C NMR, IR spectroscopy, high-resolution mass spectrometry, and elemental analysis. Full article

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

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10 pages, 945 KB

Open AccessCommunication

Development of New Amide Derivatives of Betulinic Acid: Synthetic Approaches and Structural Characterization

by Qinwei Xu, Yuhan Xie, Jin Qi, Zimo Ren, Carmine Coluccini and Paolo Coghi

Molbank 2025, 2025(4), M2072; https://doi.org/10.3390/M2072 - 13 Oct 2025

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Abstract

In this study, we report the synthesis of three new derivatives of betulinic acid, a pentacyclic triterpenoid known for its antitumor activity. These derivatives were synthesized via amide bond formation at the C-28 position using 3-[(Ethylimino)methylidene]amino-N,N-dimethylpropan-1-amine (EDC)/Hydroxybenzotriazole (HOBt) activation [...] Read more.

In this study, we report the synthesis of three new derivatives of betulinic acid, a pentacyclic triterpenoid known for its antitumor activity. These derivatives were synthesized via amide bond formation at the C-28 position using 3-[(Ethylimino)methylidene]amino-N,N-dimethylpropan-1-amine (EDC)/Hydroxybenzotriazole (HOBt) activation and various amines as nucleophiles. The synthesized compounds were characterized by nuclear magnetic resonance (NMR) techniques, including proton (¹H), carbon-13 (¹³C), COSY, HSQC, and DEPT, as well as ultraviolet–visible (UV-VIS) spectroscopy, Fourier-transform infrared (IR) and elemental analysis. This work highlights the potential of semi-synthetic modification of betulinic acid to enhance anticancer properties while addressing challenges in solubility and bioavailability. Further structural optimization and formulation studies are warranted to improve drug-like properties and therapeutic applicability. Full article

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

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9 pages, 1000 KB

Open AccessCommunication

Crystal Structure of 3-(Anthracen-2′-yl)-ortho-carborane

by Kyrill Yu. Suponitsky, Akim V. Shmal’ko, Sergey A. Anufriev and Igor B. Sivaev

Molbank 2025, 2025(4), M2071; https://doi.org/10.3390/M2071 - 10 Oct 2025

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Abstract

Crystal molecular structure of 3-(anthracen-2′-yl)-ortho-carborane was determined by single crystal X-ray diffraction study at 100 K. The asymmetric cell unit contains two enantiomeric pairs of molecules, in one of which the intramolecular dihydrogen bond CH...HB is formed with the participation of [...] Read more.

Crystal molecular structure of 3-(anthracen-2′-yl)-ortho-carborane was determined by single crystal X-ray diffraction study at 100 K. The asymmetric cell unit contains two enantiomeric pairs of molecules, in one of which the intramolecular dihydrogen bond CH...HB is formed with the participation of the C(1)H hydrogen of the anthracene substituent, and in the other with the participation of the C(3)H hydrogen. In all molecules, the polycyclic aromatic and carborane fragments are rotated relative to each other in such a way that the C-C bond of the ortho-carborane cage is approximately parallel to the plane of the aromatic substituent. According to quantum chemical calculations, the minimum energy corresponds to the formation of an intramolecular dihydrogen bond C(1)H...HB(4/7), whereas the C(3)H...HB(4/7) bond is formed rather as a result of intermolecular interactions in the crystal lattice. Full article

(This article belongs to the Section Structure Determination)

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5 pages, 262 KB

Open AccessShort Note

2,2,3,3-Tetrafluoropropyl 4-azido-2,3,5,6-Tetrafluorobenzoate

by Sofia S. Kascheeva, Anastasiya V. Lastovka, Andrey S. Vinogradov, Tatyana V. Mezhenkova and Dmitriy A. Parkhomenko

Molbank 2025, 2025(4), M2070; https://doi.org/10.3390/M2070 - 10 Oct 2025

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Abstract

Organic azides are traditionally used in organic synthesis to obtain a wide variety of chemical compounds. This prompted us to report the synthesis of a new polyfluorinated aryl azide, 2,2,3,3-tetrafluoropropyl 4-azido-2,3,5,6-tetrafluorobenzoate, which was obtained in two stages starting from pentafluorobenzoic acid. Full article

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

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7 pages, 1156 KB

Open AccessCommunication

Gas Phase Fragmentation of N,N-Ditosyl-2-aminodiphenylamine to Phenazine

by M. John Plater and William T. A. Harrison

Molbank 2025, 2025(4), M2069; https://doi.org/10.3390/M2069 - 6 Oct 2025

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Abstract

N,N-Ditosyl-2-aminodiphenylamine was prepared by the tosylation of 2-aminodiphenylamine with tosylchloride in dichloromethane. Unwanted isomers owing to the tosylation of the diarylamine were not formed. This compound was fully characterized by IR, UV/Vis, NMR, m/z, and mp, including an X-Ray [...] Read more.

N,N-Ditosyl-2-aminodiphenylamine was prepared by the tosylation of 2-aminodiphenylamine with tosylchloride in dichloromethane. Unwanted isomers owing to the tosylation of the diarylamine were not formed. This compound was fully characterized by IR, UV/Vis, NMR, m/z, and mp, including an X-Ray single crystal structure determination. It was fragmented in an Atmospheric Solids Analysis Probe (ASAP) mass spectrometer showing a series of fragments down to phenazine. Full article

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

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5 pages, 234 KB

Open AccessCommunication

Synthesis and Characterization of Novel Pyridinium Salts of (E)-2-(Pyridin-4-ylmethylene)hydrazine-1-carboximidamide

by Fatemeh Ataie Alani, Fatemeh Ahmadian, Alireza Houshdar Tehrani and Salimeh Amidi

Molbank 2025, 2025(4), M2068; https://doi.org/10.3390/M2068 - 1 Oct 2025

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Abstract

We report the synthesis and characterization of the novel pyridinium salts from (E)-2-(pyridin-4-ylmethylene)hydrazine-1-carboximidamide. The pyridinium salts were obtained via the reaction of guanylhydrazone derived from pyridine-4-carbaldehyde with phenacyl bromides. Structural characterization was carried out using IR, ¹H, and ¹³C [...] Read more.

We report the synthesis and characterization of the novel pyridinium salts from (E)-2-(pyridin-4-ylmethylene)hydrazine-1-carboximidamide. The pyridinium salts were obtained via the reaction of guanylhydrazone derived from pyridine-4-carbaldehyde with phenacyl bromides. Structural characterization was carried out using IR, ¹H, and ¹³C NMR spectroscopy and mass spectrometry. Full article

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

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Scheme 1

8 pages, 1375 KB

Open AccessShort Note

3-(4-Hydroxy-2,3,5-trimethylphenyl)-3-(4-hydroxyphenyl)isobenzofuran-1(3H)-one

by Brian A. Chalmers, David B. Cordes, Aidan P. McKay, Iain L. J. Patterson, Russell J. Pearson, Nadiia Vladymyrova and Iain A. Smellie

Molbank 2025, 2025(4), M2067; https://doi.org/10.3390/M2067 - 1 Oct 2025

Viewed by 274

Abstract

3-(4-hydroxy-2,3,5-trimethylphenyl)-3-(4-hydroxyphenyl)isobenzofuran-1(3H)-one is a derivative of the well-known acid/base indicator, phenolphthalein. We report the synthesis and the molecular structure of the title compound as determined by single-crystal X-ray diffraction. ¹H and ¹³C NMR spectroscopy, IR spectroscopy, and mass spectrometry data have been provided. Full article

(This article belongs to the Section Structure Determination)

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7 pages, 862 KB

Open AccessShort Note

Dichloro[2,5-bis(diisopropylphosphorimidoyl-κN-(4,6-dimethylpyrimidine-κN))pyrrole-κN]yttrium(III)·toluene

by Emily L. Trew, David Szucs and Paul G. Hayes

Molbank 2025, 2025(4), M2066; https://doi.org/10.3390/M2066 - 30 Sep 2025

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Abstract

The compound dichloro[bis(diisopropylphosphorimidoyl-κN-(4,6-dimethylpyrimidine-κN))pyrrole-κN]yttrium(III) was synthesized from one equivalent of NaL [L = 2,5-[ⁱPr₂P=N(Pym^Me)]₂NH(C₄H₂); Pym^Me = 4,6-dimethylpyrimidine] and YCl₃(THF)_3.5 and crystallized from [...] Read more.

The compound dichloro[bis(diisopropylphosphorimidoyl-κN-(4,6-dimethylpyrimidine-κN))pyrrole-κN]yttrium(III) was synthesized from one equivalent of NaL [L = 2,5-[ⁱPr₂P=N(Pym^Me)]₂NH(C₄H₂); Pym^Me = 4,6-dimethylpyrimidine] and YCl₃(THF)_3.5 and crystallized from toluene. X-ray quality crystals of LYCl₂ were obtained with one toluene solvent molecule in the asymmetric unit. The geometry, bond lengths and angles were analyzed and found to contain similar parameters to comparable structures in the literature, and the product was further characterized by NMR spectroscopy. To the best of our knowledge, this is the first reported seven-coordinate Y(III) complex supported by a pentadentate ligand wherein all five donor atoms are nitrogen. Full article

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6 pages, 565 KB

Open AccessShort Note

(±)-2-(4-Isobutylphenyl)-N-(naphthalen-1-yl)propanamide

by Diyana Dimitrova, Iliyan Ivanov, Stanimir Manolov and Dimitar Bojilov

Molbank 2025, 2025(4), M2065; https://doi.org/10.3390/M2065 - 30 Sep 2025

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Abstract

We describe the synthesis of (±)-2-(4-isobutylphenyl)-N-(naphthalen-1-yl)propanamide, followed by comprehensive structural characterization. The compound was analyzed through melting point determination, ¹H and ¹³C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The concordant results from these techniques provide clear evidence for [...] Read more.

We describe the synthesis of (±)-2-(4-isobutylphenyl)-N-(naphthalen-1-yl)propanamide, followed by comprehensive structural characterization. The compound was analyzed through melting point determination, ¹H and ¹³C NMR spectroscopy, infrared spectroscopy, and mass spectrometry. The concordant results from these techniques provide clear evidence for the successful preparation and structural confirmation of the target molecule. Full article

(This article belongs to the Section Structure Determination)

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Molbank, Volume 2025, Issue 4 (December 2025) – 14 articles

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