Molbank

Open AccessCommunication

Spontaneous Enantiomeric Resolution of 1,3-Diols from the Naphtylidene Derivative of 2,4-Pentanedione

by

Yair Alvarez-Ricardo

,

Dylan Sánchez-López

,

William Meza-Morales

,

Marco A. Obregón-Mendoza

,

Antonino Arenaza-Corona

,

Juan M. Germán-Acacio

,

Rubén A. Toscano

,

Miriam R. Zermeño-Ortega

,

David Morales-Morales

and

Raúl G. Enríquez

Molbank 2022, 2022(4), M1457; https://doi.org/10.3390/M1457 (registering DOI) - 30 Sep 2022

Abstract

Enantiomers (2S, 4S)- and (2R, 4R)-3-(naphthalene-1-ylmethyl) pentane-2,4-diols were synthesized by the reduction of (Z)-4-hydroxy-3-(naphthalene-1-ylmethyl) pent-3-en-2-one with NaBH₄ in methanol (MeOH). Crystallization in dichloromethane of this racemic mixture led to simple crystals with a crystalline [...] Read more.

Enantiomers (2S, 4S)- and (2R, 4R)-3-(naphthalene-1-ylmethyl) pentane-2,4-diols were synthesized by the reduction of (Z)-4-hydroxy-3-(naphthalene-1-ylmethyl) pent-3-en-2-one with NaBH₄ in methanol (MeOH). Crystallization in dichloromethane of this racemic mixture led to simple crystals with a crystalline habit with similar morphologies; however, in a group of them, it was possible to find a barely observable difference that allowed determining a crystal structure for each of the enantiomers, the 2S,4S, and the 2R,4R. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

Open AccessShort Note

2,3,4,5,6-Pentabromobenzoic Acid

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and

Victoria E. Gontcharenko

Molbank 2022, 2022(4), M1455; https://doi.org/10.3390/M1455 - 26 Sep 2022

Abstract

Pentabromobenzoate is a useful fragment in organic synthesis and in coordination chemistry. Among known synthetic approaches to pentabromobenzoic acid (PBA), we have assessed and identified exhaustive bromination of benzoic acid by using 1.3-dibromoisocyanuric acid in concentrated H₂SO₄ solution as the [...] Read more.

Pentabromobenzoate is a useful fragment in organic synthesis and in coordination chemistry. Among known synthetic approaches to pentabromobenzoic acid (PBA), we have assessed and identified exhaustive bromination of benzoic acid by using 1.3-dibromoisocyanuric acid in concentrated H₂SO₄ solution as the most efficient method for the preparation of PBA on a multigram scale. As the crude bromination product is typically contaminated with 3,4,5,6-tetrabromobenzoic acid (TBA) and pentabromobenzene, C6Br5H, a simple purification protocol for preparation of analytically pure PBA has been developed. The molecular structure and crystal packing of PBA established by single-crystal X-ray diffractometry suggests a pattern of H-bonding and halogen bonding in solid state. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

Bis(2-hydroxyethyl) 2-phenylsuccinate

by

Diego Olivieri

,

Riccardo Tarroni

and

Carla Carfagna

Molbank 2022, 2022(4), M1456; https://doi.org/10.3390/M1456 - 26 Sep 2022

Abstract

Succinic acid esters are important compounds that find many applications in various industrial fields. One of the most promising and easy ways of producing these molecules is represented by the bis-alkoxycarbonylation reaction of olefins. In particular, a recently developed catalytic system, consisting of [...] Read more.

Succinic acid esters are important compounds that find many applications in various industrial fields. One of the most promising and easy ways of producing these molecules is represented by the bis-alkoxycarbonylation reaction of olefins. In particular, a recently developed catalytic system, consisting of an aryl α-diimine/palladium(II) catalyst and p-benzoquinone as an oxidant, has allowed succinates to be obtained in high yields. A similar methodology was applied here for the unprecedented synthesis of the bis(2-hydroxyethyl) 2-phenylsuccinate in 78% isolated yield, starting from the cheap and commercially available compounds styrene and ethylene glycol. To our knowledge, no other examples of bis-alkoxycarbonylations of olefins involving diols have been reported thus far. The obtained product was fully characterized by NMR and ESI-MS analyses. Full article

(This article belongs to the Topic Catalysis: Homogeneous and Heterogeneous)

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Scheme 1

Open AccessCommunication

Assembly of Sn(IV)-Porphyrin Cation Exhibiting Supramolecular Interactions of Anion···Anion and Anion···π Systems

by

Hee-Joon Kim

Molbank 2022, 2022(4), M1454; https://doi.org/10.3390/M1454 - 25 Sep 2022

Abstract

Trans-diaqua[meso-tetrakis(4-pyridyl)porphyrinato]Sn(IV) dinitrate complexes were assembled in a two-dimensional manner via hydrogen bonding between aqua ligands and pyridyl substituents. Interestingly, this supramolecular assembly was accompanied by unconventional noncovalent interactions, such as anion···anion and anion···π interactions, which were confirmed by X-ray crystallographic [...] Read more.

Trans-diaqua[meso-tetrakis(4-pyridyl)porphyrinato]Sn(IV) dinitrate complexes were assembled in a two-dimensional manner via hydrogen bonding between aqua ligands and pyridyl substituents. Interestingly, this supramolecular assembly was accompanied by unconventional noncovalent interactions, such as anion···anion and anion···π interactions, which were confirmed by X-ray crystallographic analysis. Two nitrate anions close to 2.070 Å were constrained in a confined space surrounded by four hydrogen-bonded Sn(IV)-porphyrin cations. The nitrate anion was also 3.433 Å away from the adjacent pyrrole ring, and the dihedral angle between the two mean planes was estimated to be 7.39°. The preference of the anion···π interaction was related to the electron-deficient π-system owing to the high-valent Sn(IV) center and cationic nature of the porphyrin complex. These two unconventional noncovalent interactions played an important role in the formation of a one-dimensional array with pairs of Sn(IV)-porphyrin cation and nitrate anion. Full article

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Graphical abstract

Open AccessShort Note

Methyl 5-Imino-2-methyl-1,10a-dihydro-5H-chromeno[2,3-b]pyridine-3-carboxylate

by

Joana Pinto

,

Artur M. S. Silva

and

Vera L. M. Silva

Molbank 2022, 2022(4), M1453; https://doi.org/10.3390/M1453 - 23 Sep 2022

Abstract

Multicomponent reactions are valuable synthetic tools to deliver highly functionalized motifs starting from simple building blocks in only one step and in an atom-economical way. Herein we disclose the structure of a new and unexpected compound, the methyl 5-imino-2-methyl-1,10a-dihydro-5H-chromeno[2,3-b]pyridine-3-carboxylate, [...] Read more.

Multicomponent reactions are valuable synthetic tools to deliver highly functionalized motifs starting from simple building blocks in only one step and in an atom-economical way. Herein we disclose the structure of a new and unexpected compound, the methyl 5-imino-2-methyl-1,10a-dihydro-5H-chromeno[2,3-b]pyridine-3-carboxylate, which was formed in the ohmic-heating-assisted multicomponent Hantzsch reaction of 3-formylchromone with methyl acetoacetate and ammonium acetate, in aqueous medium, in the presence of tetrabutylammonium bromide as phase transfer catalyst. The title compound was isolated with no need of chromatographic separation and was analyzed by nuclear magnetic resonance (¹H and ¹³C-NMR, HSQC and HMBC) spectroscopy, mass spectrometry (MS) and high-resolution mass spectrometry (HRMS). Its formation as the main reaction product was observed when the reaction was performed using ohmic heating, which may lead to some speculations about the possible existence of specific effects of ohmic heating in the reactivity pathway because of the passage of an alternating electric current of high frequency within the reaction media, opening new opportunities for further investigations of the potential of this thermal processing method in organic synthesis and reactivity optimization. Full article

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Graphical abstract

Open AccessCommunication

(Diaqua)hexakis(4,4,4-trifluoro-1-(1-methyl-1H-pyrazol-4-yl)butane-1,3-dionato-κ²O,O’)(μ-(1,4-dioxane))digadolinium (III), Solvate with Two Molecules of 1,4-Dioxane

by

Ilya V. Taydakov

,

Yury A. Belousov

,

Mikhail T. Metlin

and

Victoria E. Gontcharenko

Molbank 2022, 2022(4), M1452; https://doi.org/10.3390/M1452 - 23 Sep 2022

Abstract

A binuclear gadolinium (III) complex was obtained through the interaction of GdCl₃·6H₂O, 4,4,4-trifluoro-1-(1-methyl-1H-pyrazol-4-yl)butane-1,3-dione and NaOH in MeOH solution. Molar ration of reagents equal to 1:3:3 was used. Upon recrystallization of wet 1,4-dioxane, an intermediate hydrated complex formed [...] Read more.

A binuclear gadolinium (III) complex was obtained through the interaction of GdCl₃·6H₂O, 4,4,4-trifluoro-1-(1-methyl-1H-pyrazol-4-yl)butane-1,3-dione and NaOH in MeOH solution. Molar ration of reagents equal to 1:3:3 was used. Upon recrystallization of wet 1,4-dioxane, an intermediate hydrated complex formed stable crystalline solvate with the composition [(Gd₂(L)₃(H₂O))₂(C₄H₈O₂)]•2(C₄H₈O₂). The structured of complex was established by single crystal XRD experiment. Furthermore, some photophysical properties of the complex were measured. Thus, the energy of the first exited triplet state for the diketonate ligand was found to be 22400 cm⁻¹, which makes 4,4,4-trifluoro-1-(1-methyl-1H-pyrazol-4-yl)butane-1,3-dione a promising ligand for the preparation of highly luminescent Eu³⁺ and Sm³⁺ complexes. Full article

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Open AccessShort Note

Ethyl 5-Oxo-5-(((12-oxoindolo[2,1-b]quinazolin-6(12H)-ylidene)amino)oxy)pentanoate

by

Anastasia R. Kovrizhina

,

Alina A. Kolpakova

,

Andrei A. Kuznetzov

and

Andrei I. Khlebnikov

Molbank 2022, 2022(4), M1451; https://doi.org/10.3390/M1451 - 23 Sep 2022

Abstract

Indolo[2,1-b]quinazolin-6,12-dione (tryptanthrin) derivatives present important types of nitrogen-containing heterocyclic compounds which are useful intermediate products in organic synthesis and have potential pharmaceutical applications. The new ethyl 5-oxo-5-(((12-oxoindolo[2,1-b]quinazolin-6(12H)-ylidene)amino)oxy)pentanoate (Compound 2) was synthesized. Compound 2 is the first [...] Read more.

Indolo[2,1-b]quinazolin-6,12-dione (tryptanthrin) derivatives present important types of nitrogen-containing heterocyclic compounds which are useful intermediate products in organic synthesis and have potential pharmaceutical applications. The new ethyl 5-oxo-5-(((12-oxoindolo[2,1-b]quinazolin-6(12H)-ylidene)amino)oxy)pentanoate (Compound 2) was synthesized. Compound 2 is the first example of a tryptanthrin derivative containing a dicarboxylic acid residue in the side chain. The Z,E-isomerism of Compound 2 was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, Compound 2 is potentially highly bioavailable and has the prospective to be used as the main component for the development of anti-inflammatory drugs. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

2-[Difluoro(phenylselenyl)methyl]benzo-1,3-thiazole

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Molbank 2022, 2022(4), M1450; https://doi.org/10.3390/M1450 - 22 Sep 2022

Abstract

This short note elaborates a concise protocol for the synthesis of 2-[difluoro(phenylselenyl)methyl]benzo-1,3-thiazole in two steps from the commercially available reagent 2-aminobenzenethiol. The structures of the synthesized compounds are confirmed by ¹H-NMR, ¹³C-NMR and ¹⁹F-NMR spectroscopy, infrared (IR) spectra, and high-resolution mass spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

Methyl-3-(3-hydroxy-3-(4-(piperidin-1-yl)phenyl)-prop-2-enoyl)benzoate

by

Marina A. Kiseleva

,

Sergei V. Tatarin

,

Andrei V. Churakov

and

Stanislav I. Bezzubov

Molbank 2022, 2022(4), M1449; https://doi.org/10.3390/M1449 - 20 Sep 2022

Abstract

The title compound was synthesized and characterized for the first time by ¹H, ¹³C NMR, high-resolution mass spectra and single-crystal X-ray diffraction. Full article

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Open AccessShort Note

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

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

Abstract

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

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

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

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

Abstract

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

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

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

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Open AccessShort Note

Allobetulin

by

Mirosława Grymel

and

Jakub Adamek

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

Abstract

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

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

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

by

R. Alan Aitken

,

Joe S. Logan

and

Alexandra M. Z. Slawin

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

Abstract

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

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

(This article belongs to the Section Structure Determination)

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Graphical abstract

Open AccessShort Note

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

by

Roberto E. Blanco-Carapia

,

Enrique A. Aguilar-Rangel

,

Alejandro Islas-Jácome

and

Eduardo González-Zamora

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

Abstract

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

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

(This article belongs to the Collection Heterocycle Reactions)

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Open AccessShort Note

Tris(μ₂-carbonyl)octacarbonyl(triphenylphosphite)tetracobalt

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

Abstract

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

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

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

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

by

Timofey N. Chmovzh

and

Oleg A. Rakitin

Molbank 2022, 2022(3), M1441; https://doi.org/10.3390/M1441 - 08 Sep 2022

Abstract

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

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

(This article belongs to the Section Organic Synthesis)

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Scheme 1

Open AccessShort Note

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

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Molbank 2022, 2022(3), M1442; https://doi.org/10.3390/M1442 - 08 Sep 2022

Abstract

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

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

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

Synthesis of Bisoxazole and Bromo-substituted Aryloxazoles

by

Sambasivarao Kotha

and

Subba Rao Cheekatla

Molbank 2022, 2022(3), M1440; https://doi.org/10.3390/M1440 - 06 Sep 2022

Abstract

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

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

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

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

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Molbank 2022, 2022(3), M1439; https://doi.org/10.3390/M1439 - 05 Sep 2022

Abstract

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

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

(This article belongs to the Special Issue Molecules from Side Reactions II)

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