Molbank

Open AccessShort Note

2,2’-[(1,4-Dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid)

by

Joanna Fedorowicz ,

Karol Gzella ,

Paulina Wiśniewska and

Jarosław Sączewski

Molbank 2019, 2019(4), M1093; https://doi.org/10.3390/M1093 (registering DOI) - 21 Nov 2019

Abstract

The title compound, 2,2’-[(1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and [...] Read more.

The title compound, 2,2’-[(1,4-dimethoxy-1,4-dioxobutane-2,3-diylidene)bis(azanylylidene)]bis(quinoline-3-carboxylic acid) was synthesized from isoxazolo[3,4-b]quinolin-3(1H)-one and dimethyl acetylenedicarboxylate (DMAD) via a double aza-Michael addition followed by [1,3]-H shifts. The product was characterized by infrared and nuclear magnetic resonance spectroscopy, as well as elemental analysis and high-resolution mass spectrometry (HRMS). The proposed reaction mechanism was rationalized by density functional theory (DFT) calculations. Full article

(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)

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Open AccessShort Note

1,1,4,7-Tetramethyldecahydro-1H-cyclopropa[e]azulen-7-ol from the Stembark Chisocheton pentandrus

by

Muhamad Salman Fareza ,

Nurlelasari ,

Unang Supratman ,

Dewa Gede Katja ,

Muhamad Hafiz Husna and

Khalijah Awang

Molbank 2019, 2019(4), M1092; https://doi.org/10.3390/M1092 - 20 Nov 2019

Abstract

A new aromadendrane-type sesquiterpenoid, namely dehydrosphatulenol (1), has been isolated from the stembark of Chisocheton pentandrus. The chemical structure of 1 was characterized on the basis of spectroscopic evidences including mainly one dimension and two dimension Nuclear Magnetic Resonance, and [...] Read more.

A new aromadendrane-type sesquiterpenoid, namely dehydrosphatulenol (1), has been isolated from the stembark of Chisocheton pentandrus. The chemical structure of 1 was characterized on the basis of spectroscopic evidences including mainly one dimension and two dimension Nuclear Magnetic Resonance, and Mass Spectroscopy as well as through a comparison with those related compounds previously reported. Full article

(This article belongs to the Section Natural Products)

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Open AccessShort Note

8-(Pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane

by

Vladimir A. Ogurtsov and

Oleg A. Rakitin

Molbank 2019, 2019(4), M1091; https://doi.org/10.3390/M1091 - 20 Nov 2019

Abstract

Heptasulfur imides substituted by hereterocycle may be of interest as biologically active compounds. In this communication, the reaction of pyrimidin-2-amine 1 with disulfur dichloride was carefully investigated to give 8-(pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane in good yield. The structure of the newly synthesized compound was established by [...] Read more.

Heptasulfur imides substituted by hereterocycle may be of interest as biologically active compounds. In this communication, the reaction of pyrimidin-2-amine 1 with disulfur dichloride was carefully investigated to give 8-(pyrimidin-2-yl)-1,2,3,4,5,6,7,8-heptathiazocane in good yield. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy and mass-spectrometry. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

1-Octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium Bis(trifluoromethane)sulfonimide

by

Andrea Mezzetta ,

Christian S. Pomelli ,

Felicia D’Andrea and

Lorenzo Guazzelli

Molbank 2019, 2019(4), M1089; https://doi.org/10.3390/M1089 - 19 Nov 2019

Abstract

The title compound 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide was prepared in three steps. This asymmetrical dicationic ionic liquid (ADIL) is composed of two different positively charged head groups (1-octylimidazolium and methylpyrrolidinium cations), which are linked through a propyl alkyl chain and by two bis(trifluoromethane)sulfonimide anions. The [...] Read more.

The title compound 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide was prepared in three steps. This asymmetrical dicationic ionic liquid (ADIL) is composed of two different positively charged head groups (1-octylimidazolium and methylpyrrolidinium cations), which are linked through a propyl alkyl chain and by two bis(trifluoromethane)sulfonimide anions. The final ADIL was obtained by a simple metathesis reaction of the corresponding dibromide ionic liquid, in turn prepared by alkylation of 3-(3-bromopropyl)-1-propylimidazolium bromide. The ADIL structure and those of its precursors were confirmed through NMR and infrared spectroscopy, and the thermal properties of all compounds were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Density, solubility, and viscosity were measured for the prepared compounds. Full article

(This article belongs to the Section Organic Synthesis)

Open AccessShort Note

Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2S)-2-[(1R)-1-(methylamino)-ethyl]]ferrocene-aminal

by

Philipp Honegger and

Michael Widhalm

Molbank 2019, 2019(4), M1090; https://doi.org/10.3390/M1090 - 19 Nov 2019

Abstract

In the course of an ongoing synthetic project, we observed an unprecedented reactivity of N-methyl groups in bis(N,N-dimethylaminoethylferrocenyl)phenylphosphinesulfide upon treatment with manganese dioxide (MnO₂). The intramolecular course of this reaction resulted in the formation of an [...] Read more.

In the course of an ongoing synthetic project, we observed an unprecedented reactivity of N-methyl groups in bis(N,N-dimethylaminoethylferrocenyl)phenylphosphinesulfide upon treatment with manganese dioxide (MnO₂). The intramolecular course of this reaction resulted in the formation of an unexpected homochiral diaza macrocycle. The target structure was accessible in two steps from known N,N-dimethylaminoethylferrocene. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

3-(3,4-Dimethoxyphenyl)-5-(2-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole

by

Adel Zamri ,

Neni Frimayanti and

Molbank 2019, 2019(4), M1088; https://doi.org/10.3390/M1088 - 12 Nov 2019

Abstract

A new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction under microwave irradiation. The structure of compound 1 has been established by spectroscopy analysis, including UV, FT-IR, HRMS, ¹H and ¹³C NMR spectroscopy. Based on [...] Read more.

A new analogue of fluorinated pyrazoline (compound 1) has been synthesized via one-pot three-component reaction under microwave irradiation. The structure of compound 1 has been established by spectroscopy analysis, including UV, FT-IR, HRMS, ¹H and ¹³C NMR spectroscopy. Based on the in silico studies, this compound showed a good potential as an inhibitor for dengue virus type 2 (DEN2) NS2B/NS3 serine protease and can be used as a reference in the next design of an antidengue virus. Full article

(This article belongs to the Section Organic Synthesis)

Open AccessShort Note

6-Bromo-N-(2-methyl-2H-benzo[d][1,2,3]triazol-5-yl)quinolin-4-amine

by

Christopher R. M. Asquith and

Graham J. Tizzard

Molbank 2019, 2019(4), M1087; https://doi.org/10.3390/M1087 - 27 Oct 2019

Cited by 1

Abstract

We describe a straightforward synthesis of the title compound, incorporating a relatively rare 2-methyl-2H-1,2,3-triazole heterocylic motif as a potential kinase inhibitor motif. The small molecule crystal structure has been resolved, revealing an interesting packing arrangement and overall conformation. We also performed [...] Read more.

We describe a straightforward synthesis of the title compound, incorporating a relatively rare 2-methyl-2H-1,2,3-triazole heterocylic motif as a potential kinase inhibitor motif. The small molecule crystal structure has been resolved, revealing an interesting packing arrangement and overall conformation. We also performed routine characterization with ¹H/¹³C-NMR and liquid chromatography (LC) and high-resolution mass spectra (HRMS). Full article

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Open AccessFeature PaperCommunication

Synthesis of 2-Cyanopyrimidines

by

Andreas S. Kalogirou and

Panayiotis A. Koutentis

Molbank 2019, 2019(4), M1086; https://doi.org/10.3390/M1086 - 22 Oct 2019

Cited by 1

Abstract

4,6-Dichloro-2-(methylthio)pyrimidine (7) was converted to 4-chloro-6-methoxy-2-(methylthio)pyrimidine (15) and 4,6-dimethoxy-2-(methylthio)pyrimidine (14). Chlorination of the latter with N-chlorosuccinimide (NCS) affords 5-chloro-4,6-dimethoxy-2-(methylthio)pyrimidine (16) in 56% yield. Both methylthiopyrimidines 15 and 14 were converted in two steps to [...] Read more.

4,6-Dichloro-2-(methylthio)pyrimidine (7) was converted to 4-chloro-6-methoxy-2-(methylthio)pyrimidine (15) and 4,6-dimethoxy-2-(methylthio)pyrimidine (14). Chlorination of the latter with N-chlorosuccinimide (NCS) affords 5-chloro-4,6-dimethoxy-2-(methylthio)pyrimidine (16) in 56% yield. Both methylthiopyrimidines 15 and 14 were converted in two steps to 4-chloro-6-methoxypyrimidine-2-carbonitrile (13) and 4,6-dimethoxypyrimidine-2-carbonitrile (12), respectively, after oxidation to sulfones and displacement of the sulfinate group with KCN. 4,6-Dimethoxypyrimidine-2-carbonitrile (12) was chlorinated with NCS to give 5-chloro-4,6-dimethoxypyrimidine-2-carbonitrile (10) in 53% yield. All new compounds were fully characterized. Full article

(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)

Open AccessCommunication

Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies

by

Sergiy M. Kovalenko ,

Oleksandr G. Drushlyak ,

Irina S. Konovalova ,

Illia O. Mariutsa ,

Dmitry V. Kravchenko ,

Alexandre V. Ivachtchenko and

Oleg D. Mitkin

Molbank 2019, 2019(4), M1085; https://doi.org/10.3390/M1085 - 14 Oct 2019

Abstract

A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, ¹H NMR, ¹³C NMR, LC/MS [...] Read more.

A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2-(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, ¹H NMR, ¹³C NMR, LC/MS and single crystal X-ray diffraction. UV/Vis and IR spectra of compounds are described. The presence of a strong intramolecular hydrogen bond between the hydroxy group and the carbonyl oxygen atom of the ester group in methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate is shown. The crystal structure of product was stabilized through intermolecular hydrogen bonds. Full article

(This article belongs to the Special Issue Heterocycle Reactions)

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Open AccessCommunication

Reactions of Polychlorinated Pyrimidines with DABCO

by

Andreas S. Kalogirou and

Panayiotis A. Koutentis

Molbank 2019, 2019(4), M1084; https://doi.org/10.3390/M1084 - 14 Oct 2019

Abstract

The reaction of 2,4,5,6-tetrachloropyrimidine (4) and 4,5,6-trichloropyrimidine-2-carbonitrile (1) with DABCO (1 equiv.), in MeCN, at ca. 20 °C gives 2,4,5-trichloro-6-[4-(2-chloroethyl)piperazin-1-yl]pyrimidine (5) and 4,5-dichloro-6-[4-(2-chloroethyl)piperazin-1-yl]pyrimidine-2-carbonitrile (6) in 42% and 52% yields, respectively. The new compounds were fully characterized. Full article

(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)

Open AccessShort Note

3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione

by

Nadine Uwabagira and

Balladka Kunhana Sarojini

Molbank 2019, 2019(4), M1083; https://doi.org/10.3390/M1083 - 03 Oct 2019

Abstract

The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human [...] Read more.

The compound 3-{[(2,3-Dichlorophenyl)amino]methyl}-5-(furan-2-ylmethylidene)-1,3-thiazolidine-2,4-dione has been designed, synthesized, and screened for its in vitro antibreast cancer activity, using human breast adenocarcinoma cell lines (MCF-7) and in vitro anti-inflammatory activity. By hemolysis assay, it showed that it has a nonhemolytic and nontoxic effect on human blood cell. The title compound 5, subjected to in vitro activities, showed that it is cytotoxic with an IC₅₀ of 42.30 µM and a good anti-inflammatory agent. The docking results against cyclin dependent kinase 2 (CDK2) (PDB ID: 3QQK) gave insights on its inhibitory activity. Full article

(This article belongs to the Special Issue Heterocycle Reactions)

Open AccessShort Note

2-{[Bis(propan-2-yl)carbamothioyl]sulfanyl}acetic acid

by

See Mun Lee ,

Ainnul Hamidah Syahadah Azizan ,

Kong Mun Lo ,

Sang Loon Tan and

Edward R. T. Tiekink

Molbank 2019, 2019(4), M1082; https://doi.org/10.3390/M1082 - 20 Sep 2019

Cited by 1

Abstract

The title compound, (iPr)₂NC(=S)SCH₂C(=O)OH (1), was synthesized by conventional methods and its X-ray crystal structure was determined by X-ray crystallography. The compound was further characterized by analytical, IR, UV, 1D NMR (¹H and ¹³C{ [...] Read more.

The title compound, (iPr)₂NC(=S)SCH₂C(=O)OH (1), was synthesized by conventional methods and its X-ray crystal structure was determined by X-ray crystallography. The compound was further characterized by analytical, IR, UV, 1D NMR (¹H and ¹³C{¹H}), and 2D NMR (DEPT-135) spectroscopy, and density functional theory (DFT) methods. X-ray crystallography on 1 confirms the formulation and reveals a nearly orthogonal relationship between the planar NCS₂ and C₂O₂ residues. In the crystal, hydroxyl-O–H⋯O(carbonyl) hydrogen bonds lead dimers via an eight-membered {⋯OCOH}₂ ring. Full article

(This article belongs to the Section Structure Determination)

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Open AccessShort Note

(E)-4-(3-Phenylisoxazol-5-yl)but-3-en-2-one

by

Nattawut Sawengngen ,

Alexandra A. Kolodina and

Olga V. Serdyuk

Molbank 2019, 2019(3), M1081; https://doi.org/10.3390/M1081 - 18 Sep 2019

Abstract

(E)-4-(3-Phenylisoxazol-5-yl)but-3-en-2-one was synthesized via the oxidative ring opening reaction of 2-(5-methylfuran-2-yl)-1-phenylethanone oxime, followed by the iodine mediated isomerization. Full article

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

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Open AccessShort Note

Digyaindoleacid A: 2-(1-(4-Hydroxyphenyl)-3-oxobut-1-en-2-yloxy)-3-(1H-indol-3-yl)propanoic Acid, a Novel Indole Alkaloid

by

Samuel Kwain ,

Gilbert Mawuli Tetevi ,

Thomas Mensah ,

Anil Sazak Camas ,

Mustafa Camas ,

Aboagye Kwarteng Dofuor ,

Faustus Akankperiwen Azerigyik ,

Hai Deng ,

Marcel Jaspars and

Kwaku Kyeremeh

Molbank 2019, 2019(3), M1080; https://doi.org/10.3390/M1080 - 14 Sep 2019

Abstract

Digyaindoleacid A (1) is one of the novel alkaloids produced by the Ghanaian Paenibacillus sp. DE2SH (GenBank Accession Number: MH091697) isolated from the mangrove rhizosphere soils of the Pterocarpus santalinoides tree growing in the wetlands of the Digya National Park, Brong [...] Read more.

Digyaindoleacid A (1) is one of the novel alkaloids produced by the Ghanaian Paenibacillus sp. DE2SH (GenBank Accession Number: MH091697) isolated from the mangrove rhizosphere soils of the Pterocarpus santalinoides tree growing in the wetlands of the Digya National Park, Brong Ahafo Region, Ghana. This compound was isolated on HPLC at t_R ≈ 60 min and its structure determined by MS, 1D, and 2D-NMR data. When tested against Trypanosoma brucei subsp. brucei strain GUTat 3.1, 1 produced a half-maximal inhibitory concentration (IC₅₀) 5.21 μM compared to the standard diminazene aceturate (IC₅₀ = 1.86 μM). In the presence of normal mouse macrophages RAW 264.7, 1 displayed a higher selectivity towards T. brucei subsp. brucei (selectivity indices (SI) = 30.2) with low toxicity. This result is interesting given that the drug diminazene aceturate is considerably toxic and 1 is a natural product isolate. The structure of 1 incorporates the backbone of the amino acid tryptophan which is crucial in the metabolism of Trypanosoma brucei subsp. brucei strain GUTat 3.1. It is possible that 1, could interfere with the normal uptake and metabolism of tryptophan in the parasite. However, 1 (IC₅₀ = 135.41 μM) produced weak antileishmanial activity when tested against Leishmania donovani (Laveran and Mesnil) Ross (D10). Full article

(This article belongs to the Section Natural Products)

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Open AccessShort Note

2-(3,4-Dimethoxyphenyl)-N-(4-methoxyphenyl)-1-propyl-1H-benzo[d]imidazole-5-carboxamide

by

Prakash Bhaskar ,

Vasantha Kumar ,

Suresha Kumara Tholappanavara Hanumanthappa and

Sowmya Haliwana Banakara Vijaykumar

Molbank 2019, 2019(3), M1079; https://doi.org/10.3390/M1079 - 09 Sep 2019

Abstract

2-(3,4-Dimethoxyphenyl)-N-(4-methoxyphenyl)-1-propyl-1H-benzo[d]imidazole-5-carboxamide was synthesized by the ‘one-pot’ reductive cyclization of N-(4-methoxyphenyl)-3-nitro-4-(propylamino)benzamide with 3,4-dimethoxybenzaldehyde, using sodium dithionite as a reductive cyclizing agent using DMSO as a solvent. The structure of newly synthesized compound was elucidated based on IR, ¹H-NMR, ¹³C-NMR, and LC-MS data. Full article

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

Open AccessCommunication

A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity

by

Oxana B. Kazakova ,

Jean Michel Brunel ,

Elmira F. Khusnutdinova ,

Sophie Negrel ,

Gulnara V. Giniyatullina ,

Tatyana V. Lopatina and

Anastasiya V. Petrova

Molbank 2019, 2019(3), M1078; https://doi.org/10.3390/M1078 - 06 Sep 2019

Abstract

Synthesis of A-ring-modified lupane, oleanane and ursane type triterpenoid conjugates with spermidine through an aldimine linkage or diethylentriamine via an amide bond is described. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. Except for derivatives 1 and 7 [...] Read more.

Synthesis of A-ring-modified lupane, oleanane and ursane type triterpenoid conjugates with spermidine through an aldimine linkage or diethylentriamine via an amide bond is described. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. Except for derivatives 1 and 7, all compounds have moderate to weak minimum inhibitory concentrations (MICs) against Gram-positive Staphylococcus aureus bacteria, with MICs varying from 3.125 to 200 µM. Compound 11 is efficient against Escherichia coli and Pseudomonas aeruginosa, with MICs of 25 and 50 µM, respectively, while all other derivatives do not possess important antimicrobial activities against these Gram-negative bacteria. Full article

(This article belongs to the Section Natural Products)

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Open AccessShort Note

2-(3,5-Dimethyl-1H-pyrazol-1-yl)thiazolo[4,5-b]pyridine

by

Honghong Lan ,

Min Zheng and

Ye Wang

Molbank 2019, 2019(3), M1077; https://doi.org/10.3390/M1077 - 20 Aug 2019

Abstract

The compound 2-(3,5-dimethyl-1H-pyrazol-1-yl)thiazolo[4,5-b]pyridine (1) was synthesized with a yield of 71% by the reaction of 1-(thiazolo[4,5-b]pyridine-2-yl)hydrazine and acetylacetone. The structure was characterized by a single-crystal X-ray structure determination as well as ¹H and ¹³ [...] Read more.

The compound 2-(3,5-dimethyl-1H-pyrazol-1-yl)thiazolo[4,5-b]pyridine (1) was synthesized with a yield of 71% by the reaction of 1-(thiazolo[4,5-b]pyridine-2-yl)hydrazine and acetylacetone. The structure was characterized by a single-crystal X-ray structure determination as well as ¹H and ¹³C{¹H} NMR spectroscopy. X-ray crystallography on 1 confirms the molecule consists of a pyridine–thiazole moiety and the pyrazole ring, and all non-hydrogen atoms are planar. Full article

Open AccessShort Note

Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate

by

Itamar Luís Gonçalves , Gabriel Oliveira de Azambuja,

Leonardo Davi , Guilherme Arraché Gonçalves, Luciano Porto Kagami, Gustavo Machado das Neves,

João Pedro Silveira , Rômulo Faria Santos Canto and

Vera Lucia Eifler-Lima

Molbank 2019, 2019(3), M1076; https://doi.org/10.3390/M1076 - 14 Aug 2019

Abstract

The Biginelli reaction is an acid-catalyzed, three-component reaction between an aldehyde, a hydrogen methylene active compound, and urea (or its analogue) and constitutes a rapid and easy synthesis of highly functionalized heterocycles. Synthesis of ethyl 6-methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate, identified by our laboratory code [...] Read more.

The Biginelli reaction is an acid-catalyzed, three-component reaction between an aldehyde, a hydrogen methylene active compound, and urea (or its analogue) and constitutes a rapid and easy synthesis of highly functionalized heterocycles. Synthesis of ethyl 6-methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate, identified by our laboratory code LaSOM^® 293, was achieved using the Biginelli reaction as the key step, followed by the Huisgen 1,3-dipolar cycloaddition in a convergent four-step route. The product LaSOM^® 293 was obtained with a yield of 84%. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

N-Benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide

by

Hamad H. Al Mamari ,

Nasser Al Awaimri and

Yousuf Al Lawati

Molbank 2019, 2019(3), M1075; https://doi.org/10.3390/M1075 - 29 Jul 2019

Abstract

The title compound, N-benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide (1) was synthesized by reacting 3-trifluoromethylbenzoyl chloride (4) and 4-aminobenzo[c][1,2,5]thiadiazole (5). The compound was characterized by various spectroscopic methods (¹H NMR, ¹³C NMR, IR, GC-MS) [...] Read more.

The title compound, N-benzo[c][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide (1) was synthesized by reacting 3-trifluoromethylbenzoyl chloride (4) and 4-aminobenzo[c][1,2,5]thiadiazole (5). The compound was characterized by various spectroscopic methods (¹H NMR, ¹³C NMR, IR, GC-MS) and its composition confirmed by elemental analysis. The importance of this compound lies in its possession of an N,N-bidentate directing group. Such a structural motif is potentially suitable for metal-catalyzed C-H bond functionalization reactions. Full article

(This article belongs to the Section Organic Synthesis)

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