Molbank

5 pages, 402 KiB

Open AccessCommunication

New Derivatives of Lupeol and Their Biological Activity

by Hoang-Thuy-Tien Le, Quoc-Cuong Chau, Thuc-Huy Duong, Quyen-Thien-Phuc Tran, Nguyen-Kim-Tuyen Pham, Thi-Hoai-Thu Nguyen, Ngoc-Hong Nguyen and Jirapast Sichaem

Molbank 2021, 2021(4), M1306; https://doi.org/10.3390/M1306 - 10 Dec 2021

Cited by 3 | Viewed by 3201

Abstract

The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures [...] Read more.

The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures were elucidated by spectroscopic analyses (HRESIMS and NMR). Compounds 3 showed significant α-glucosidase inhibition with an IC₅₀ value of 202 µM, whereas 2a and 2b were inactive. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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7 pages, 575 KiB

Open AccessCommunication

4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline

by Peter G. Larson and David M. Ferguson

Molbank 2021, 2021(4), M1305; https://doi.org/10.3390/M1305 - 9 Dec 2021

Cited by 3 | Viewed by 2464

Abstract

4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in [...] Read more.

4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in arriving at the thiazoloquinoline-5N-oxide intermediate using electron deficient aromatic systems. Here, we demonstrate a synthetic route to obtain substituted thiazoloquinolines with electron-withdrawing groups at the C7 position. The target compound, 4-amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline, is obtained in eight steps using a 7-bromo surrogate as a precursor to the successful generation of the N-oxide intermediate, and final transformation via Pd-mediated C7-acylation. Full article

(This article belongs to the Special Issue Quinoline, Derivatives and Applications)

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5 pages, 525 KiB

Open AccessShort Note

2-(2-(4-Methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic Acid

by Boris V. Lichitsky, Andrey N. Komogortsev and Valeriya G. Melekhina

Molbank 2021, 2021(4), M1304; https://doi.org/10.3390/M1304 - 9 Dec 2021

Cited by 6 | Viewed by 2560

Abstract

For the first time, we describe a new approach towards the synthesis of previously unknown 2-(2-(4-methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic acid. The presented method is based on the multicomponent condensation of 5-hydroxy-4,7-dimethyl-2H-chromen-2-one, 4-methoxyphenylglyoxal and Meldrum’s acid. It was shown that the [...] Read more.

For the first time, we describe a new approach towards the synthesis of previously unknown 2-(2-(4-methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic acid. The presented method is based on the multicomponent condensation of 5-hydroxy-4,7-dimethyl-2H-chromen-2-one, 4-methoxyphenylglyoxal and Meldrum’s acid. It was shown that the studied reaction proceeds in two steps including the initial interaction of starting materials in MeCN and the final formation of furylacetic acid moiety in acidic media. The structures of the obtained compound were established by ¹H, ¹³C-NMR spectroscopy and high-resolution mass spectrometry. Full article

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

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11 pages, 1924 KiB

Open AccessArticle

An Efficient Synthesis of Novel 3-[(Heteroaryl-2-ylimino)-methyl]-4-hydroxy-chromen-2-ones and Analogue of Tetrazole Derivatives and Their Antibacterial Activity

by Ramiz Hoti, Hamit Ismaili, Veprim Thaçi, Gjyle Mulliqi-Osmani, Malësore Pllana-Zeqiri and Agon Bytyqi

Molbank 2021, 2021(4), M1303; https://doi.org/10.3390/M1303 - 2 Dec 2021

Cited by 1 | Viewed by 2493

Abstract

Synthesis of a series of the substituted [(pyridinyl and pyrimidin-2-ylimino)-ethyl]-4-hydroxy-chromen-2-ones and their tetrazole derivates is presented in this study. By catalytic condensation of 4-hydroxy-3-acetylcoumarine 2 and 2-aminopyridines 3(a-d), 3-[(pyridin-2-ylimino)-ethyl]-4-hydroxy-chromen-2-ones 4(a-d) are synthesized in high yield. During the condensation reaction of 2 and [...] Read more.

Synthesis of a series of the substituted [(pyridinyl and pyrimidin-2-ylimino)-ethyl]-4-hydroxy-chromen-2-ones and their tetrazole derivates is presented in this study. By catalytic condensation of 4-hydroxy-3-acetylcoumarine 2 and 2-aminopyridines 3(a-d), 3-[(pyridin-2-ylimino)-ethyl]-4-hydroxy-chromen-2-ones 4(a-d) are synthesized in high yield. During the condensation reaction of 2 and 4-amino-2,6-dihydroxypyrimidine 3e, 3-[1-(2,6-Dihydroxy-pyrimidin-4-ylimino)-ethyl]-4-hydroxy-chromen-2-one 4e as condensation products is synthesized. In following series, by cyclization reactions of compounds 4 (a-e) with sodium azide, analogue 3-substituted pyridin-2-yl and pyrimidin-2-yl-5-methyl-2,5-dihydro-1H-tetrazol-5-yl]-4-hydroxy-chromen-2-one 5(a-e) are synthesized the products. Structural characterization of the synthesized products is done on the basis of spectrometric data. Antibacterial activity of the compounds 4(a-e) and 5(a-e) against S. aureus, E. coli and Klebsiella was examined by measuring the inhibition zones around the disks marked with the corresponding products solution. The impact of substitutions in antimicrobial is also explored. Compounds with polar groups have shown significant antibacterial activity against these microorganisms. Full article

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

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5 pages, 970 KiB

Open AccessCommunication

4,4’-(Pyridin-4-ylmethylene)dibenzonitrile

by Ben M. J. Lancaster, Alexander J. Nicholls and Ian R. Baxendale

Molbank 2021, 2021(4), M1302; https://doi.org/10.3390/M1302 - 30 Nov 2021

Viewed by 2636

Abstract

This communication describes an unprecedented substitution cascade, in which 4-methylpyridine, following deprotonation with LDA, twice acts as a carbon nucleophile in an unusual S_NAr process, to form a novel triarylmethane structure. A proposed mechanism for this sequence is presented that is [...] Read more.

This communication describes an unprecedented substitution cascade, in which 4-methylpyridine, following deprotonation with LDA, twice acts as a carbon nucleophile in an unusual S_NAr process, to form a novel triarylmethane structure. A proposed mechanism for this sequence is presented that is supported by single crystal X-ray analysis of the resulting product. We believe this unique transformation is of note as it highlights a neat and efficient entry as a single step to complex triarylmethane architectures containing both substituted phenyl and pyridyl aromatics. Full article

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

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5 pages, 889 KiB

Open AccessShort Note

Potassium (3-Methyl-2-oxido-1,2,5-oxadiazol-4-yl)dinitromethanide

by Egor S. Zhilin, Dmitry B. Meerov and Leonid L. Fershtat

Molbank 2021, 2021(4), M1301; https://doi.org/10.3390/M1301 - 26 Nov 2021

Viewed by 2143

Abstract

Furoxan derivatives enriched with explosophoric functionalities are promising compounds in the preparation of novel energetic materials. Herein, a previously unknown potassium (3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)dinitromethanide (also referred to as potassium 4-dinitromethyl-3-methylfuroxanate) was synthesized via tandem nitration-reduction reactions of an available (furoxanyl)chloroxime. The structure of the synthesized [...] Read more.

Furoxan derivatives enriched with explosophoric functionalities are promising compounds in the preparation of novel energetic materials. Herein, a previously unknown potassium (3-methyl-2-oxido-1,2,5-oxadiazol-4-yl)dinitromethanide (also referred to as potassium 4-dinitromethyl-3-methylfuroxanate) was synthesized via tandem nitration-reduction reactions of an available (furoxanyl)chloroxime. The structure of the synthesized compound was established by elemental analysis, IR, ¹H, ¹³C and ¹⁴N NMR spectroscopy. Thermal stability and mechanical sensitivity of the prepared compound toward impact and friction were experimentally determined. Full article

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

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7 pages, 2131 KiB

Open AccessCommunication

CF₃-Bis-TEMPO-Vis: New Visible Light Active Bis-Benzimidazolequinone Alkoxyamine

by Patrick Kielty, Pau Farràs, Dennis A. Smith and Fawaz Aldabbagh

Molbank 2021, 2021(4), M1300; https://doi.org/10.3390/M1300 - 26 Nov 2021

Viewed by 2482

Abstract

Alkoxyamines of TEMPO usually dissociate thermally at >100 °C; however, room temperature homolysis, activated by visible light, occurs with benzimidazolequinone derivatives. 1,1’-Dimethyl-2,2’-bis{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-6-(trifluoromethyl)-1H,1’H-[5,5’-bibenzimidazole]-4,4’,7,7’-tetrone (CF₃-Bis-TEMPO-Vis) is prepared in a 59% yield through NBS/H₂SO₄ oxidative [...] Read more.

Alkoxyamines of TEMPO usually dissociate thermally at >100 °C; however, room temperature homolysis, activated by visible light, occurs with benzimidazolequinone derivatives. 1,1’-Dimethyl-2,2’-bis{[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]methyl}-6-(trifluoromethyl)-1H,1’H-[5,5’-bibenzimidazole]-4,4’,7,7’-tetrone (CF₃-Bis-TEMPO-Vis) is prepared in a 59% yield through NBS/H₂SO₄ oxidative demethylations of the dimethoxybenzimidazole-benzimidazolequinone precursor with aqueous work up. The alternative basic work up in air gave the epoxide derivative of CF₃-Bis-TEMPO-Vis. Unlike the latter CF₃-epoxide, both alkoxyamine residues are labile under green light (470–600 nm), and the rate of TEMPO release is three times slower than Bis-TEMPO-Vis. Full article

(This article belongs to the Collection Heterocycle Reactions)

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7 pages, 1095 KiB

Open AccessShort Note

11H-Indeno[1,2-b]quinoxalin-11-one 2-(4-ethylbenzylidene)hydrazone

by Anastasia R. Kovrizhina, Elizaveta I. Samorodova and Andrei I. Khlebnikov

Molbank 2021, 2021(4), M1299; https://doi.org/10.3390/M1299 - 23 Nov 2021

Cited by 4 | Viewed by 2989

Abstract

11H-Indeno[1,2-b]quinoxaline derivatives present an important type of nitrogen-containing heterocyclic compound that are useful intermediate products in organic synthesis and have potential pharmaceutical applications. A new 11H-indeno[1,2-b]quinoxalin-11-one-2-(4-ethylbenzylidene)hydrazone (compound 3) was synthesized. Compound 3 is the [...] Read more.

11H-Indeno[1,2-b]quinoxaline derivatives present an important type of nitrogen-containing heterocyclic compound that are useful intermediate products in organic synthesis and have potential pharmaceutical applications. A new 11H-indeno[1,2-b]quinoxalin-11-one-2-(4-ethylbenzylidene)hydrazone (compound 3) was synthesized. Compound 3 is the first example of an azine derivative based on the 11H-indeno[1,2-b]quinoxaline system. The Z,E-isomerism of compound 3 was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, compound 3 is potentially highly bioavailable and has potential to be used for the treatment of neuroinflammation and ischemia–reperfusion injury. Full article

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

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5 pages, 1932 KiB

Open AccessShort Note

Bis(pyrazol-1-yl)methane-4,4′-dicarboxylic Acid

by Elizaveta A. Pershina, Dmitry I. Pavlov, Nikita P. Burlutskiy and Andrei S. Potapov

Molbank 2021, 2021(4), M1298; https://doi.org/10.3390/M1298 - 22 Nov 2021

Cited by 3 | Viewed by 2270

Abstract

The molecular structure of bis(pyrazol-1-yl)methane-4,4′-dicarboxylic acid (H₂bpmdc) was determined by single crystal X-Ray diffraction analysis. The compound crystallizes in a monoclinic crystal system; the unit cell contains four formula units. The molecules of H₂bpmdc are linked into zig-zag chains [...] Read more.

The molecular structure of bis(pyrazol-1-yl)methane-4,4′-dicarboxylic acid (H₂bpmdc) was determined by single crystal X-Ray diffraction analysis. The compound crystallizes in a monoclinic crystal system; the unit cell contains four formula units. The molecules of H₂bpmdc are linked into zig-zag chains by intermolecular carboxyl–carboxyl hydrogen bonds. Other types of supramolecular interactions, namely, CH···N and CH···O short contacts, CH–π interactions and carbonyl–carbonyl interactions were detected in the crystal structure. Full article

(This article belongs to the Section Structure Determination)

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Graphical abstract

5 pages, 510 KiB

Open AccessShort Note

2,2′-(1,4-Phenylene)bis(7-nitro-1H-benzimidazole 3-oxide)

by Fabrizio Politano, Ana K. Gran-Magano and Nicholas E. Leadbeater

Molbank 2021, 2021(4), M1297; https://doi.org/10.3390/M1297 - 22 Nov 2021

Viewed by 2119

Abstract

Bis(benzimidazol-2-yl-3-oxide)benzene derivatives have potential applications as energetic or photoactive materials. By using a two-step one-pot approach employing microwave heating as a tool, 2,2′-(1,4-phenylene)bis(7-nitro-1H-benzimidazole 3-oxide) (1) has been prepared in 94% yield. In the first step an S_NAr [...] Read more.

Bis(benzimidazol-2-yl-3-oxide)benzene derivatives have potential applications as energetic or photoactive materials. By using a two-step one-pot approach employing microwave heating as a tool, 2,2′-(1,4-phenylene)bis(7-nitro-1H-benzimidazole 3-oxide) (1) has been prepared in 94% yield. In the first step an S_NAr reaction is performed using p-xylylenediamine as the central building block. Without isolating the intermediate, a base-mediated cyclization reaction follows in the second step. The product was isolated in analytically pure form by means of a pH-controlled precipitation. Full article

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

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5 pages, 542 KiB

Open AccessCommunication

Regioselective Synthesis of 4-Bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide

by Sukanta Bar and Maxwell Israel Martin

Molbank 2021, 2021(4), M1296; https://doi.org/10.3390/M1296 - 16 Nov 2021

Cited by 2 | Viewed by 2484

Abstract

We synthesized 4-bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide by using three successive direct lithiations and a bromination reaction starting from thiophene. All these lithiation reactions were carried out at −78 °C to RT over a period of 1 to 24 h based on the reactivity of [...] Read more.

We synthesized 4-bromo-3-formyl-N-phenyl-5-propylthiophene-2-carboxamide by using three successive direct lithiations and a bromination reaction starting from thiophene. All these lithiation reactions were carried out at −78 °C to RT over a period of 1 to 24 h based on the reactivity of electrophile. This is a four-step protocol starting from thiophene with an overall yield of 47%. Full article

(This article belongs to the Collection Heterocycle Reactions)

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4 pages, 369 KiB

Open AccessShort Note

4,7-Bis(1,2,3,4,4a,9a-Hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine

by Timofey N. Chmovzh, Karim S. Gaisin and Oleg A. Rakitin

Molbank 2021, 2021(4), M1295; https://doi.org/10.3390/M1295 - 5 Nov 2021

Cited by 2 | Viewed by 2174

Abstract

New donor-acceptor-donor (D-A-D)-type structures are widely used to design effective organic light-emitting diodes (OLEDs). In this communication, 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained in a 65% yield by the treatment of 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide with 2,3,4,4a,9,9a-hexahydro-1H-carbazole. The structure of [...] Read more.

New donor-acceptor-donor (D-A-D)-type structures are widely used to design effective organic light-emitting diodes (OLEDs). In this communication, 4,7-bis(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-[1,2,5]oxadiazolo[3,4-d]pyridazine was obtained in a 65% yield by the treatment of 4,7-dichloro[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide with 2,3,4,4a,9,9a-hexahydro-1H-carbazole. The structure of the newly synthesized compounds was established by means of an elemental analysis, ¹H, ¹³C NMR, IR and UV spectroscopy, and HRMS and LR mass-spectrometry. Full article

(This article belongs to the Collection Heterocycle Reactions)

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5 pages, 560 KiB

Open AccessShort Note

6-(Chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

by Vladimir A. Ogurtsov and Oleg A. Rakitin

Molbank 2021, 2021(4), M1294; https://doi.org/10.3390/M1294 - 1 Nov 2021

Cited by 1 | Viewed by 2392

Abstract

Functionally 4,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1H-pyrazolo[3,4-d]pyrimidines are practically unexplored derivatives in this series. In this paper, it was shown that the nucleophilic substitution of 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine [...] Read more.

Functionally 4,6-disubstituted 1H-pyrazolo[3,4-d]pyrimidines are important compounds with various pharmacological activities. 1-Substituted 4-chloro-6-(chloromethyl)-1H-pyrazolo[3,4-d]pyrimidines are practically unexplored derivatives in this series. In this paper, it was shown that the nucleophilic substitution of 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine with methylamine produced selectively 4-substituted product, 6-(chloromethyl)-N,1-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. The structure of the synthesized compound was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C-NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis. Full article

(This article belongs to the Collection Heterocycle Reactions)

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5 pages, 877 KiB

Open AccessShort Note

(E)-5-(Methoxyimino)-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one

by Irina Ihnatenko, Peter G. Jones and Conrad Kunick

Molbank 2021, 2021(4), M1293; https://doi.org/10.3390/M1293 - 29 Oct 2021

Cited by 1 | Viewed by 2158

Abstract

(E)-5-(Methoxyimino)-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one was prepared by a condensation reaction from 3,4-dihydro-1H-benzo[b]azepin-2,5-dione and O-methylhydroxylamine. The configuration at the C=N double bond was determined by X-ray crystallography. Full article

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5 pages, 3192 KiB

Open AccessCommunication

Multicomponent Approach to the Synthesis of 4-(1H-indol-3-yl)-5-(4-methoxyphenyl)furan-2(5H)-one

by Andrey N. Komogortsev, Boris V. Lichitsky and Valeriya G. Melekhina

Molbank 2021, 2021(4), M1292; https://doi.org/10.3390/M1292 - 29 Oct 2021

Cited by 4 | Viewed by 2421

Abstract

A simple one-pot approach was developed for the synthesis of furan-2(5H)-one derivative containing indole fragments. This method includes the telescoped multicomponent reaction of indole, 4-methoxyphenylglyoxal, and Meldrum’s acid. The synthetic utility of the prepared furan-2(5H)-one was demonstrated by condensation [...] Read more.

A simple one-pot approach was developed for the synthesis of furan-2(5H)-one derivative containing indole fragments. This method includes the telescoped multicomponent reaction of indole, 4-methoxyphenylglyoxal, and Meldrum’s acid. The synthetic utility of the prepared furan-2(5H)-one was demonstrated by condensation with 4-methoxybenzaldehyde. The advantages of this method include the employment of readily accessible starting materials, atom economy, process simplicity, and the easy isolation of the target products. The structure of the synthesized furanones was confirmed by ¹H and ¹³C-NMR spectroscopy and high-resolution mass spectrometry with electrospray ionization (ESI-HRMS). Full article

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

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4 pages, 347 KiB

Open AccessShort Note

4,7-Bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine

by Timofey N. Chmovzh, Timofey A. Kudryashev and Oleg A. Rakitin

Molbank 2021, 2021(4), M1291; https://doi.org/10.3390/M1291 - 25 Oct 2021

Cited by 2 | Viewed by 2508

Abstract

Bis(alkylsulfanyl) derivatives of 1,2,5-thiadiazoles fused with aromatic and heteroaromatic rings containing long alkyl chains are of interest as compounds with liquid crystalline properties. In this communication, 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 was obtained from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2 by a combination of two reactions—aromatic [...] Read more.

Bis(alkylsulfanyl) derivatives of 1,2,5-thiadiazoles fused with aromatic and heteroaromatic rings containing long alkyl chains are of interest as compounds with liquid crystalline properties. In this communication, 4,7-bis(dodecylthio)-[1,2,5]thiadiazolo[3,4-c]pyridine 1 was obtained from 4,7-dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine 2 by a combination of two reactions—aromatic nucleophilic substitution S_NAr and Buchwald–Hartwig cross-coupling. The structure of the newly synthesized compounds was established by means of elemental analysis; high-resolution mass spectrometry; ¹H, ¹³C NMR, IR and UV spectroscopy; and mass spectrometry. Full article

(This article belongs to the Special Issue Heteroatom Rich Organic Heterocycles)

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3 pages, 532 KiB

Open AccessShort Note

N,N-Bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)thiophen-2-amine

by Timofey N. Chmovzh and Oleg A. Rakitin

Molbank 2021, 2021(4), M1290; https://doi.org/10.3390/M1290 - 21 Oct 2021

Viewed by 2388

Abstract

N,N-Diarylthiophen-2-amine units are of great interest for the synthesis of optoelectronic devices. In this communication, N,N-bis (4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)thiophen-2-amine was obtained by means of a Buchwald–Hartwig cross-coupling reaction of bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine and 2-bromothiophene in the presence of tris(dibenzylideneacetone)dipalladium(0), tri-tert [...] Read more.

N,N-Diarylthiophen-2-amine units are of great interest for the synthesis of optoelectronic devices. In this communication, N,N-bis (4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)thiophen-2-amine was obtained by means of a Buchwald–Hartwig cross-coupling reaction of bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine and 2-bromothiophene in the presence of tris(dibenzylideneacetone)dipalladium(0), tri-tert-butyl phosphine and sodium tert-butanolate. The structure of newly synthesized compounds was established by means of elemental analysis, high-resolution mass spectrometry, ¹H, ¹³C NMR, IR and UV spectroscopy and mass-spectrometry. Full article

(This article belongs to the Special Issue Metal-Catalyzed Synthesis)

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4 pages, 1121 KiB

Open AccessCommunication

Regioselective Synthesis of 5-Propyl-2-((trityloxy)methyl)thiophene-3-carbaldehyde

by Sukanta Bar

Molbank 2021, 2021(4), M1289; https://doi.org/10.3390/M1289 - 14 Oct 2021

Cited by 2 | Viewed by 2592

Abstract

5-propyl-2-((trityloxy)methyl)thiophene-3-carbaldehyde was synthesized by using the concept of chemo- and regioselective Br/Li exchange reaction from 3-bromo-5-propyl-2-((trityloxy)methyl)thiophene. This is a five-step protocol starting from thiophene with an overall yield of 33%. These lithium/halogen exchange reactions were carried out at −78 °C to rt over [...] Read more.

5-propyl-2-((trityloxy)methyl)thiophene-3-carbaldehyde was synthesized by using the concept of chemo- and regioselective Br/Li exchange reaction from 3-bromo-5-propyl-2-((trityloxy)methyl)thiophene. This is a five-step protocol starting from thiophene with an overall yield of 33%. These lithium/halogen exchange reactions were carried out at −78 °C to rt over the period of 1 to 18 h depending on the reactivity of electrophiles. Full article

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

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7 pages, 1816 KiB

Open AccessCommunication

Novel Synthesis of N-Acetylcysteine Medicine Using an Effective Method

by Farzaneh Ziaee and Mohammad Ziaee

Molbank 2021, 2021(4), M1288; https://doi.org/10.3390/M1288 - 13 Oct 2021

Cited by 1 | Viewed by 9454

Abstract

N-acetylcysteine (NAC) is mainly administrated as a mucolytic medication, antioxidant supplement, antidote in paracetamol overdose, and a drug for the prevention of diabetic kidney disease. Its effect has been investigated for the treatment of several diseases such as COVID-19. In this work, [...] Read more.

N-acetylcysteine (NAC) is mainly administrated as a mucolytic medication, antioxidant supplement, antidote in paracetamol overdose, and a drug for the prevention of diabetic kidney disease. Its effect has been investigated for the treatment of several diseases such as COVID-19. In this work, an effective method for high-yield synthesis of N-acetylcysteine is proposed. This drug can be synthesized in a single-batch step instead of using a multi-stage process. The proposed method has shown the potential to be considered as an alternative method for producing NAC. The purification process was carried out using suitable solvents to reach a high level of purity. The characterization of the synthesized drug was undertaken through Elemental analysis, Proton Nuclear Magnetic Resonance (¹H NMR), High Performance Liquid Chromatography (HPLC), Fourier Transform Infrared Spectroscopy (FT-IR), and melting point analyses. Full article

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6 pages, 933 KiB

Open AccessShort Note

3-[N-(4-Methoxybenzyl)amino]benzo[de]anthracen-7-one

by Alise Kirilova, Aleksandrs Pučkins, Sergey Belyakov and Elena Kirilova

Molbank 2021, 2021(4), M1287; https://doi.org/10.3390/M1287 - 11 Oct 2021

Cited by 2 | Viewed by 2350

Abstract

Herein, we describe the synthesis of 3-[N-(4-methoxybenzyl)amino]benzo[de]anthracen-7-one via a two-step procedure including 3-aminobenzanthrone condensation with anisaldehyde and following reduction of obtained imine to appropriate amine by sodium borohydride. The structure of the synthesized compounds was established by elemental analysis, [...] Read more.

Herein, we describe the synthesis of 3-[N-(4-methoxybenzyl)amino]benzo[de]anthracen-7-one via a two-step procedure including 3-aminobenzanthrone condensation with anisaldehyde and following reduction of obtained imine to appropriate amine by sodium borohydride. The structure of the synthesized compounds was established by elemental analysis, nuclear magnetic resonance spectroscopy, mass spectrometry (EI-MS), and infrared spectroscopy (FT-IR) and confirmed by single-crystal X-ray diffraction. The title compound was analyzed by thermal gravimetric analysis, UV/vis, and fluorescence spectroscopy. Full article

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

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6 pages, 6297 KiB

Open AccessShort Note

8-[4-(2-Hydroxypropane-2-yl)phenyl]-1,3,4,4,5,7-hexamethyl-4-boron-3a,4a-diaza-S-indacene

by Anastasiya Zobnina, Alexander Moskalensky and Aleksey Vorob’ev

Molbank 2021, 2021(4), M1286; https://doi.org/10.3390/M1286 - 8 Oct 2021

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Abstract

During recent years, the BODIPY core became a popular scaffold for designing photoremovable protecting groups (PPG). In this paper, we report the synthesis of a new molecule—8-[4-(2-hydroxypropane-2-yl)phenyl]-1,3,4,4,5,7-hexamethyl-4-boron-3a,4a-diaza-S-indacene—by the treatment of meso-(4-CO₂Me-phenyl)-BODIPY with excess of [...] Read more.

During recent years, the BODIPY core became a popular scaffold for designing photoremovable protecting groups (PPG). In this paper, we report the synthesis of a new molecule—8-[4-(2-hydroxypropane-2-yl)phenyl]-1,3,4,4,5,7-hexamethyl-4-boron-3a,4a-diaza-S-indacene—by the treatment of meso-(4-CO₂Me-phenyl)-BODIPY with excess of MeMgI. The product was characterized by ¹H, ¹³C NMR and HRMS. The combination of BODIPY core with tertiary benzilyc alcohol might be promising for utilizing this molecule as visible light removable PPG. Full article

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

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12 pages, 3788 KiB

Open AccessShort Note

Naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate

by Serigne Abdou Khadir Fall, Sara Hajib, Oumaima Karai, Salaheddine Boukhssas, Younas Aouine, Mohamed Akhazzane, Brahim Labriti, Hassane Faraj and Anouar Alami

Molbank 2021, 2021(4), M1285; https://doi.org/10.3390/M1285 - 4 Oct 2021

Cited by 1 | Viewed by 2767

Abstract

We have previously published new biheterocyclic phospohonic α-amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to [...] Read more.

We have previously published new biheterocyclic phospohonic α-amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to the same catalytic process used previously, the compound naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate was synthesized with an excellent yield and high regioselectivity via the copper (I)-catalyzed alkyne–azide cycloaddition reaction (CuAAC), using diethyl (α-azido(benzamido)methyl)phosphonate (1) as a dipole and 2- naphthyl propiolate as a dipolarophile (2). The structure of the new compound was fully characterized by 1D (³¹P, ¹H-, ¹³C-) and 2D (¹H-¹H and ¹H-, ¹³C-) NMR spectroscopy, IR, and HRMS. Full article

(This article belongs to the Special Issue Metal-Catalyzed Synthesis)

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10 pages, 1172 KiB

Open AccessShort Note

Synthesis and Characterization of Novel Thiazolidinones and Thioxothiazolidinones Derived from Substituted Indole

by Nawel Rekiba, Abdelmadjid Benmohammed, Sofiane Khanoussi, Ayada Djafri and Jérôme Thibonnet

Molbank 2021, 2021(4), M1284; https://doi.org/10.3390/M1284 - 30 Sep 2021

Cited by 2 | Viewed by 2972

Abstract

Based on recent discoveries concerning the numerous biological properties of thiazolidinones and thiosemicarbazones, new N-substituted heterocyclic derivatives have been designed by combining the indole ring with thioxothiazolidinone, thiazolidinone or thiosemicarbazone. Thus, a series of new thioxothiazolidinone, thiazolidinone, or thiosemicarbazone derivatives bearing indole-based [...] Read more.

Based on recent discoveries concerning the numerous biological properties of thiazolidinones and thiosemicarbazones, new N-substituted heterocyclic derivatives have been designed by combining the indole ring with thioxothiazolidinone, thiazolidinone or thiosemicarbazone. Thus, a series of new thioxothiazolidinone, thiazolidinone, or thiosemicarbazone derivatives bearing indole-based moiety have been designed, synthesized, and developed in good yields. Full article

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6 pages, 1290 KiB

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2,2-Bis(phenylselanyl)-1-(p-tolyl)vinyl 2-Oxo-2-(p-tolyl)acetate

by Shintaro Kodama, Vu Thai Hung, Tomokazu Saeki, Kei Mihara, Yuki Yamamoto, Motohiro Sonoda, Akihiro Nomoto and Akiya Ogawa

Molbank 2021, 2021(4), M1283; https://doi.org/10.3390/M1283 - 28 Sep 2021

Viewed by 2031

Abstract

2,2-Bis(phenylselanyl)-1-(p-tolyl)vinyl 2-oxo-2-(p-tolyl)acetate was synthesized via the reaction of p-tolylacetylene with diphenyl diselenide and benzoyl peroxide in benzene under atmospheric conditions. The molecular structure of the synthesized compound was evaluated using single-crystal X-ray analysis and spectral analyses. The process [...] Read more.

2,2-Bis(phenylselanyl)-1-(p-tolyl)vinyl 2-oxo-2-(p-tolyl)acetate was synthesized via the reaction of p-tolylacetylene with diphenyl diselenide and benzoyl peroxide in benzene under atmospheric conditions. The molecular structure of the synthesized compound was evaluated using single-crystal X-ray analysis and spectral analyses. The process reported here provides a rare example of the direct and selective transformation of a terminal alkyne to the corresponding geminal diseleno-substituted alkene. Full article

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

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5 pages, 207 KiB

Open AccessEditorial

Nitrogen-Containing Molecules: Natural and Synthetic Products including Coordination Compounds

by Dimitris Matiadis and Eleftherios Halevas

Molbank 2021, 2021(4), M1282; https://doi.org/10.3390/M1282 - 27 Sep 2021

Cited by 4 | Viewed by 2236

Abstract

Nitrogen constitutes one of the most crucial elements in synthetic compounds, both in organic and in coordination chemistry [...] Full article

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

6 pages, 533 KiB

Open AccessShort Note

5-[4-(tert-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one

by Serhii Holota, Andrii Lozynskyi, Yulian Konechnyi, Yulia Shepeta and Roman Lesyk

Molbank 2021, 2021(4), M1281; https://doi.org/10.3390/M1281 - 24 Sep 2021

Cited by 1 | Viewed by 2517

Abstract

The Knoevenagel reaction is an essential synthetic tool in the organic and medicinal chemistry of thiazolidin-4-one derivatives. In the present work, the application of ethylenediamine diacetate (EDDA) as an effective catalyst for the interaction of 2-thioxothiazolidin-4-one with 4-(tert-butyl)cyclohexanone is proposed. The [...] Read more.

The Knoevenagel reaction is an essential synthetic tool in the organic and medicinal chemistry of thiazolidin-4-one derivatives. In the present work, the application of ethylenediamine diacetate (EDDA) as an effective catalyst for the interaction of 2-thioxothiazolidin-4-one with 4-(tert-butyl)cyclohexanone is proposed. The structure of novel synthesized 5-[4-(tert-butyl)cyclohexylidene]-2-thioxothiazolidin-4-one (yield 61%) was confirmed by ¹H-, ¹³C-NMR, LC-MS, IR, and UV spectra. Drug-like properties of the synthesized compound were evaluated in silico using the SwissAdme, and their potential antimicrobial activity against 15 strains of Gram-positive and Gram-negative bacteria as well as yeasts was evaluated in vitro. The synthesized compound possesses satisfactory drug-like parameters and promising antimicrobial properties and presents interest as a prospective intermediate for the forthcoming design of biologically active small molecules. Full article

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Molbank, Volume 2021, Issue 4 (December 2021) – 26 articles

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