Molbank

Open AccessShort Note

Ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

by Itamar Luís Gonçalves, Luciano Porto Kagami, Gustavo Machado das Neves, Liliana Rockenbach, Leonardo Davi, Alceu Felipe Soares, Solange Cristina Garcia and Vera Lucia Eifler-Lima

Molbank 2018, 2018(4), M1029; https://doi.org/10.3390/M1029 - 13 November 2018

Abstract

The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using

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The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using a functionalized thiourea. In silico studies demonstrated that the compound title showed good potential for interacting with ecto-5’-nucleotidase, which has been considered as a target in designs for anti-cancer drugs. Full article

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Open AccessShort Note

[O-Isopropyl-N-(4-nitrophenyl)thiocarbamato-κS]-(tri-4-tolylphosphine-κP)gold(I)

by Chien Ing Yeo and Edward R. T. Tiekink

Molbank 2018, 2018(4), M1028; https://doi.org/10.3390/M1028 - 5 November 2018

Abstract

The synthesis, spectroscopic characterization and X-ray crystal structure of the title compound, (4-tolyl)₃PAu[SC(O-i-Pr)=NC₆H₄NO₂-4] (1) are described. Spectroscopy exhibited the expected features confirming the formation of the compound. The molecular structure of

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The synthesis, spectroscopic characterization and X-ray crystal structure of the title compound, (4-tolyl)₃PAu[SC(O-i-Pr)=NC₆H₄NO₂-4] (1) are described. Spectroscopy exhibited the expected features confirming the formation of the compound. The molecular structure of 1 confirms the expected linear P–Au–S coordination geometry defined by thiolate-S and phosphane-P atoms. The nearly 7° deviation from linearity is ascribed to the close approach of the imine-bound phenyl group, indicative of a semi-localized Au^…π(arene) interaction. The three-dimensional molecular packing is consolidated by methyl- and tolyl-C–H^…O(nitro) and tolyl-C–H^…π(tolyl) interactions. Full article

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Open AccessShort Note

(E)-3-[3-(4-Morpholinophenyl)acryloyl]-2H-chromen-2-one

by Hery Suwito, Helda Dwi Hardiyanti, Kautsar Ul Haq, Alfinda Novi Kristanti and Miratul Khasanah

Molbank 2018, 2018(4), M1027; https://doi.org/10.3390/M1027 - 29 October 2018

Abstract

A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the

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A new compound (E)-3-[3-(4-morpholinophenyl)acryloyl]-2H-chromen-2-one, a coumarin based chalcone derivative, has been successfully synthesized employing a molecular hybridization method through the reaction between 3-acetylcoumarin and 4-morpholinobenzaldehyde using a Claisen–Schmidt reaction using pTSA as a catalyst. The structure of the title compound was established using spectroscopic data FTIR, HRESI-MS, ¹H- and ¹³C-NMR. The anticancer activity against breast cancer cells line T47D and cervix cancer cells line HeLa was determined using an MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Full article

Open AccessShort Note

Dichlorido(η⁶-p-cymene)[tris(2-cyanoethyl)phosphine]ruthenium(II)

by William Henderson, Ashwin Gopalan Nair, Nathan R. Halcovich and Edward R. T. Tiekink

Molbank 2018, 2018(4), M1025; https://doi.org/10.3390/M1025 - 12 October 2018

Abstract

The tris(2-cyanoethyl)phosphine (tcep) complex [RuCl₂{P(CH₂CH₂CN)₃}(η⁶-p-cymene)] (p-cymene = p-CH₃C₆H₄ⁱPr) was synthesised by the bridge-splitting reaction of the chlorido-dimer [RuCl₂(

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The tris(2-cyanoethyl)phosphine (tcep) complex [RuCl₂{P(CH₂CH₂CN)₃}(η⁶-p-cymene)] (p-cymene = p-CH₃C₆H₄ⁱPr) was synthesised by the bridge-splitting reaction of the chlorido-dimer [RuCl₂(η⁶-p-cymene)]₂ with tcep. The complex was characterised by a single-crystal X-ray structure determination as well as NMR spectroscopy, ESI mass spectrometry, and microelemental analysis. X-ray crystallography shows the ruthenium atom is coordinated by p-cymene in a η⁶-fashion, two chlorides and the phosphorus atom of the tcep ligand with the donor set defining a distorted octahedral geometry. The ESI mass spectrometry study reveals that the complex readily forms negative ions [M + Cl]⁻ and [2M + Cl]⁻ by association with a chloride ion. Full article

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Open AccessFeature PaperShort Note

2,3,4-Trioxo-1-(1H-pyrrolo[2,3-b]pyridin-7-ium-7yl)-cyclobutan-1-ide

by Duc Hoàng Lande, Conrad Kunick and Johann Grünefeld

Molbank 2018, 2018(4), M1026; https://doi.org/10.3390/M1026 - 12 October 2018

Abstract

2,3,4-Trioxo-1-(1H-pyrrolo[2,3-b]pyridin-7-ium-7-yl)-cyclobutan-1-ide was obtained by reaction of squaric acid with 7-azaindole in acetic anhydride. Full article

Open AccessCommunication

Purine-Furan and Purine-Thiophene Conjugates

by Zigfrīds Kapilinskis, Irina Novosjolova and Māris Turks

Molbank 2018, 2018(4), M1024; https://doi.org/10.3390/M1024 - 8 October 2018

Abstract

Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a S

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Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a S_NAr and a Suzuki–Miyaura reaction and their photophysical properties were studied. Quantum yields in the solution reached up to 88% but only up to 5% in the thin layer. Full article

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Open AccessCommunication

1-Methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole

by Jean Guillon, Solène Savrimoutou, Sandra Rubio and Vanessa Desplat

Molbank 2018, 2018(4), M1023; https://doi.org/10.3390/M1023 - 4 October 2018

Abstract

The 1-methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole compound has been successfully synthesized via a multistep pathway starting from 2-phenylindole. Structure characterization of this new indole derivative was done by FTIR, ¹H-NMR, ¹³C-NMR, and HRMS spectral analysis. The title compound showed high cytotoxic potential against

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The 1-methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole compound has been successfully synthesized via a multistep pathway starting from 2-phenylindole. Structure characterization of this new indole derivative was done by FTIR, ¹H-NMR, ¹³C-NMR, and HRMS spectral analysis. The title compound showed high cytotoxic potential against five leukemia cell lines (K562, HL60, U937, U266, and Jurkat cell lines). Full article

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Open AccessCommunication

Synthesis of 4-(2H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one via Ring-Switching Hydrazinolysis of 5-Ethoxymethylidenethiazolo [3,2-b][1,2,4]triazol-6-one

by Serhii Holota, Yaroslav Shylych, Halyna Derkach, Olexandr Karpenko, Andrzej Gzella and Roman Lesyk

Molbank 2018, 2018(4), M1022; https://doi.org/10.3390/M1022 - 1 October 2018

Abstract

4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation

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4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation with chloroacetic acid under Williamson reaction conditions, and further one-pot cyclization–condensation with triethylorthoformate in the acetic anhydride medium, yielding compound 3. The structures of compounds 3 and 4 were confirmed by LC-MS, NMR spectra and a single X-ray diffraction analysis (for compound 4). Full article

Open AccessShort Note

6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone

by Yordanka Ivanova, Antonya Todorova, Christo Chanev and Ognyan Petrov

Molbank 2018, 2018(4), M1021; https://doi.org/10.3390/M1021 - 30 September 2018

Abstract

The title compound, 6-[1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2(3H)-benzoxazolone, was synthesized by condensation of 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone (1) and hydrazine hydrate in acetic acid in 84% yield. The structure of the target compound was confirmed using ¹H-NMR, ¹³C-NMR, IR, MS, and elemental analysis. Full article

Open AccessShort Note

O-Methyl m-Tolylcarbamothioate

by Chien Ing Yeo and Edward R. T. Tiekink

Molbank 2018, 2018(3), M1020; https://doi.org/10.3390/M1020 - 15 September 2018

Abstract

The synthesis, spectroscopic, and crystallographic characterisation of the title compound, O-methyl m-tolylcarbamothioate, MeOC(=S)N(H)(m-tolyl) (1), are described. The crystallographic study confirms the structure determined by spectroscopy and shows the presence of the thioamide tautomer, a syn-disposition of

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The synthesis, spectroscopic, and crystallographic characterisation of the title compound, O-methyl m-tolylcarbamothioate, MeOC(=S)N(H)(m-tolyl) (1), are described. The crystallographic study confirms the structure determined by spectroscopy and shows the presence of the thioamide tautomer, a syn-disposition of the thione-S and thioamide-N-H atoms and, in the crystal, thioamide-N-H^…S(thione) hydrogen bonding leading to an eight-membered {^…HNCS}₂ synthon. Full article

Open AccessShort Note

(E)-1-(2′,4′-Dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one

by Afzal Shaik, Mahamuda Sultana Shaik and Srinivasa Babu Puttagunta

Molbank 2018, 2018(3), M1019; https://doi.org/10.3390/M1019 - 13 September 2018

Abstract

Thiazole and chalcone motifs are of research interest to medicinal chemists due to their array of synthetic and biological utility. Hence, in the present study we intended to prepare (E)-1-(2′,4′-dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one (3c) containing both these scaffolds. The compound 3c was

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Thiazole and chalcone motifs are of research interest to medicinal chemists due to their array of synthetic and biological utility. Hence, in the present study we intended to prepare (E)-1-(2′,4′-dimethyl)-(5-acetylthiazole)-(2,4″-difluorophenyl)-prop-2-en-1-one (3c) containing both these scaffolds. The compound 3c was synthesized by the acid-catalyzed condensation of 2,4-dimethyl-5-acetylthiazole with 2,4-difluorobenzaldehyde. Purification and characterization of the compound were carried out by recrystallization and spectral techniques including UV, IR, ¹H-NMR, ¹³C-NMR, Mass spectrometry and X-ray powdered diffractometry. The molecule 3c was successfully synthesized, purified, and characterized. Full article

Open AccessFeature PaperShort Note

5-Amino-3-(diethylamino)-5H-benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine 1,1-Dioxide

by Victor Tran, Craig M. Forsyth and Craig L. Francis

Molbank 2018, 2018(3), M1018; https://doi.org/10.3390/M1018 - 11 September 2018

Abstract

In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N

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In the quest for discovery of novel bioactive molecules, new heterocyclic ring systems provide templates for exploration of uncharted chemical space. Herein, we describe the synthesis of a new benzo[4,5]imidazo[1,2-b][1,2,4,6]thiatriazine derivative from readily available 1,2-diaminobenzimidazole and N,N-diethyl-N′-chlorosulfonyl chloroformamidine. The product structure, confirmed by X-ray crystallography, bears an exocyclic NH₂ group, which should enable synthesis of an extended range of derivatives of this unusual scaffold. Full article

Open AccessFeature PaperShort Note

(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

by Raffaella Mancuso, Rossana Miliè, Ida Ziccarelli, Mariangela Novello, Nicola Della Ca’ and Bartolo Gabriele

Molbank 2018, 2018(3), M1017; https://doi.org/10.3390/M1017 - 31 August 2018

Abstract

(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100 °C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of

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(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100 °C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of a 4:1 mixture of CO–air and in the presence of the catalytic system PdI₂/KI (substrate:KI:PdI₂ molar ratio = 100:10:1), to give the oxazolidinone derivative in 81% isolated yield. Full article

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Open AccessShort Note

(1R,5S)-6-(4-Methyl-2-oxo-2,5-dihydrofuran-3-yl)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one

by Dong-Jun Fu, Victor Pham, Matthew-Alexander Tippin, Liankun Song, Xiaolin Zi, En Zhang and Hong-Min Liu

Molbank 2018, 2018(3), M1016; https://doi.org/10.3390/M1016 - 30 August 2018

Abstract

Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS

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Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS in this work. It is worth noting that compound 9 is an entirely new compound. Additionally, a plausible mechanism and effects on the formation of 9 by different Lewis acids were proposed. The discovery of compound 9 could improve the purity of this feasible industrial synthesis and provide considerable cost savings. Full article

Open AccessFeature PaperShort Note

(3-Ammonio-2,2-dimethyl-propyl)carbamate Dihydrate

by Jaqueline Heimgert, Dennis Neumann and Guido J. Reiss

Molbank 2018, 2018(3), M1015; https://doi.org/10.3390/M1015 - 29 August 2018

Abstract

(3-Ammonio-2,2-dimethylpropyl)carbamate dihydrate was synthesised. The title compound was characterised by single crystal X-ray diffraction and IR-/Raman-spectroscopy. It has been demonstrated that a mixture of dilute acetic acid and 2,2-dimethyl-1,3-diaminopropane is able to capture CO₂ spontaneously from the atmosphere. An intramolecular hydrogen bond

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(3-Ammonio-2,2-dimethylpropyl)carbamate dihydrate was synthesised. The title compound was characterised by single crystal X-ray diffraction and IR-/Raman-spectroscopy. It has been demonstrated that a mixture of dilute acetic acid and 2,2-dimethyl-1,3-diaminopropane is able to capture CO₂ spontaneously from the atmosphere. An intramolecular hydrogen bond stabilises the conformation of the ylide-type title molecule. Intermolecular hydrogen bonds between all moieties connect them to a strand-type chain structure. Full article

Open AccessFeature PaperShort Note

1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine

by Ganesh Shimoga, Eun-Jae Shin and Sang-Youn Kim

Molbank 2018, 2018(3), M1014; https://doi.org/10.3390/M1014 - 24 August 2018

Abstract

1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine (3) has been successfully synthesized by reacting p-toluic hydrazide (1) and glycine (2) via the polyphosphoric acid condensation route. The course of the reaction was found to be high yielding (87%) and the title compound

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1-[5-(4-Tolyl)-1,3,4-oxadiazol-2-yl]methanamine (3) has been successfully synthesized by reacting p-toluic hydrazide (1) and glycine (2) via the polyphosphoric acid condensation route. The course of the reaction was found to be high yielding (87%) and the title compound was spectroscopically characterized by UV-Vis, FTIR, DSC, ¹³C/¹H-NMR, and sass spectrometric techniques. Full article

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Open AccessShort Note

5-[3-(4-Bromophenyl)-1-(2,5-dimethoxyphenyl)-3-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-tri-one

by Hery Suwito, Ria Hesty Purnama Sari, Kautsar Ul Haq and Alfinda Novi Kristanti

Molbank 2018, 2018(3), M1013; https://doi.org/10.3390/M1013 - 23 August 2018

Abstract

The title compound was prepared by a two-step reaction. The first step was the formation of a chalcone derivative using Claisen–Schmidt condensation, which was followed by the Michael addition of the formed chalcone with 1,3-dimethylbarbituric acid. The structure of the prepared compound was

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The title compound was prepared by a two-step reaction. The first step was the formation of a chalcone derivative using Claisen–Schmidt condensation, which was followed by the Michael addition of the formed chalcone with 1,3-dimethylbarbituric acid. The structure of the prepared compound was established by spectral data: FTIR, HRESIMS, ¹H- and ¹³C-NMR. Full article

Open AccessShort Note

N-(4-Bromophenyl)methoxycarbothioamide

by Chien Ing Yeo and Edward R.T. Tiekink

Molbank 2018, 2018(3), M1012; https://doi.org/10.3390/M1012 - 17 August 2018

Abstract

The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the

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The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the asymmetric unit of 1. The C‒S and C‒N bond lengths confirm the presence of the thioamide tautomer. The thione-S and amide-N‒H atoms are syn, enabling the formation of amide-N‒H^…S(thione) hydrogen bonds between the two independent molecules that generates a two-molecule aggregate via an eight-membered {^…HNCS}₂ synthon. The aggregates are connected into a three-dimensional architecture via weak intermolecular interactions, including Br^…π(4-bromophenyl), S^…π(4-bromophenyl), and weak Br^…S halogen bonding contacts. The overall molecular conformation, thioamide tautomer, and the presence of amide-N‒H^…S(thione) hydrogen bonding in the crystal conform with expectation for this class of compound. Full article

Open AccessShort Note

3-(3,5-Difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

by Naveen Kumar, Swamy Sreenivasa, Vasantha Kumar and Nadigar Revansiddappa Mohan

Molbank 2018, 2018(3), M1011; https://doi.org/10.3390/M1011 - 1 August 2018

Abstract

Vilsmeier–Haack reaction of (E)-1-[1-(3,5-difluorophenyl)ethylidene]-2-phenylhydrazine (1) using dimethyl formamide in excess of phosphorus oxychloride by conventional method, resulted in the synthesis of the title compound 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4- carbaldehyde (2) in good yield and high purity. Structure characterization

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Vilsmeier–Haack reaction of (E)-1-[1-(3,5-difluorophenyl)ethylidene]-2-phenylhydrazine (1) using dimethyl formamide in excess of phosphorus oxychloride by conventional method, resulted in the synthesis of the title compound 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4- carbaldehyde (2) in good yield and high purity. Structure characterization of the title compound was done by IR, ¹H-NMR, ¹³C-NMR and HRMS spectral analysis. Full article

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