scholarly journals Selectfluor-triggered fluorination/cyclization of o-hydroxyarylenaminones: A facile access to 3-fluoro-chromones

2020 ◽  
pp. 174751982092308
Author(s):  
Yanqin Wang ◽  
Biao Hu ◽  
Qiaohe Zhang ◽  
Siyun Zhao ◽  
Yuxuan Zhao ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
13C Nmr ◽  
Potassium Carbonate ◽  
High Resolution Mass Spectrometry ◽  
Reactive Intermediates ◽  
Cyclization Reaction ◽  
Plausible Mechanism ◽  
Tandem Cyclization ◽  
Resolution Mass

A fast and efficient Selectfluor-triggered fluorination/cyclization reaction of o-hydroxyarylenaminones has been successfully developed. The reaction successfully provides an expedient method for the synthesis of 3-fluoro-chromones promoted by potassium carbonate, which shows readily available starting materials and is easy to operate. In addition, a plausible mechanism of this tandem cyclization reaction was proposed where 4 H-chromen-4-one, 2-(dimethylamino)-3,3-difluorochroman-4-one, and 3,3-difluoro-2-hydroxychroman-4-one were not found to be the reactive intermediates. Moreover, these novel compounds have been obtained in moderate to good yields, and their structures have been confirmed by 1H NMR, 13C NMR, and high-resolution mass spectrometry.

scholarly journals 4-(7-Bromobenzo[d][1,2,3]thiadiazol-4-yl)morpholine

Molbank ◽  
10.3390/m1202 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1202
Author(s):  
Nikita Gudim ◽  
Ekaterina Knyazeva ◽  
Natalia Obruchnikova ◽  
Oleg Rakitin ◽  
Vadim Popov
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
13C Nmr ◽  
High Resolution Mass Spectrometry ◽  
Nitrogen Heterocycles ◽  
X Ray ◽  
Photovoltaic Materials ◽  
Resolution Mass

Dibromoderivatives of benzofused chalcogen-nitrogen heterocycles are important precursors in the synthesis of various photovoltaic materials. 4,7-Dibromobenzo[d][1,2,3]thiadiazole is a practically unexplored compound in this series. In this communication, it was shown that the nucleophilic substitution of 4,7-dibromobenzo[d][1,2,3]thiadiazole with morpholine gave selectively 4-substituted product—4-(7-bromobenzo[d][1,2,3]thiadiazol-4-yl)morpholine. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR, and IR spectroscopy, mass-spectrometry, and X-ray analysis.

scholarly journals 8,18-Dithia-1,4,11,14-tetraazapentacyclo[11.7.0.03,11.05,9.015,19]icosa-3,5(9),6,13,15(19),16-hexaene-10,20-dione

Molbank ◽  
10.3390/m1056 ◽  
2019 ◽  
Vol 2019 (2) ◽  
pp. M1056
Author(s):  
Vladimir A. Ogurtsov ◽  
Oleg A. Rakitin
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
13C Nmr ◽  
High Resolution Mass Spectrometry ◽  
Biologically Active ◽  
Active Compounds ◽  
Dimerization Product ◽  
Resolution Mass

4H-3λ2-Thieno[3,2-d]pyrimidin-4-one derivatives are of interest as biologically active compounds. In this communication, 2-(chloromethyl)-4H-3λ2-thieno[3,2-d]pyrimidin-4-one (1) was investigated in the reaction with ammonia, potassium phthalimide, and other basic agents. The dimerization product—8,18-dithia-1,4,11,14-tetrazapentacyclo[11.7.0.03,11.05,9.015,19]icosa-3,5(9),6,13,15(19),16-hexaene-10,20-dione was formed in the reaction with potassium phthalimide in DMF, by heating at 110 °C for 5 h. 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.

scholarly journals 3,6-Dibromopyridazine-4,5-diamine

Molbank ◽  
10.3390/m1053 ◽  
2019 ◽  
Vol 2019 (1) ◽  
pp. M1053
Author(s):  
Timofey Chmovzh ◽  
Ekaterina Knyazeva ◽  
Olga Ustimenko ◽  
Oleg Rakitin
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Sodium Methoxide ◽  
High Resolution Mass Spectrometry ◽  
Photovoltaic Materials ◽  
High Resolution Mass ◽  
Derivatives Of ◽  
Resolution Mass

Dihalogenated derivatives of 1,2,5-chalcogenadiazoles fused with benzene or heterocyclic rings are of interest as starting compounds for photovoltaic materials. The 1,2,5-chalcogenadiazole ring in these heterocycles was most commonly prepared from the corresponding ortho-diamine moiety. In this communication, 3,6-dibromopyridazine-4,5-diamine was prepared via the reaction of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with sodium methoxide in THF by heating at reflux for four hours. The structure of the newly synthesized compound was established by means of high resolution mass-spectrometry, 1H, 13C-NMR and IR spectroscopy, and mass-spectrometry.

scholarly journals (2,3-Dihydro-1H-indol-5-ylmethyl)amine

Molbank ◽  
10.3390/m1248 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1248
Author(s):  
Vladimir A. Ogurtsov ◽  
Oleg A. Rakitin
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
13C Nmr ◽  
High Resolution Mass Spectrometry ◽  
Pharmacological Properties ◽  
High Resolution Mass ◽  
Resolution Mass

New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy and mass-spectrometry. The resulting compound is a convenient intermediate for various disubstituted 1-(indolin-5-yl)methanamines, which may be of interest as substances with useful pharmacological properties.

scholarly journals 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Molbank ◽  
10.3390/m1253 ◽  
2021 ◽  
Vol 2021 (3) ◽  
pp. M1253
Author(s):  
Vladimir Ogurtsov ◽  
Oleg Rakitin
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
13C Nmr ◽  
High Resolution Mass Spectrometry ◽  
Pharmacological Properties ◽  
High Resolution Mass ◽  
Resolution Mass

A novel 4-chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was prepared by a rational and short two-step synthesis from commercially available ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate via 6-(chloromethyl)-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one. The structure of the synthesized compounds was established by elemental analysis, high-resolution mass-spectrometry, 1H, 13C-NMR and IR spectroscopy and mass-spectrometry. 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine is a convenient intermediate for various disubstituted 1-methyl-1H-pyrazolo[3,4-d]pyrimidines, which may be of interest as substances with useful pharmacological properties.

scholarly journals Ethyl 11a,12-Dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate

Molbank ◽  
10.3390/m1149 ◽  
2020 ◽  
Vol 2020 (3) ◽  
pp. M1149 ◽  
Author(s):  
Lidia S. Konstantinova ◽  
Mikhail A. Tolmachev ◽  
Vadim V. Popov ◽  
Oleg A. Rakitin
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Heterocyclic System ◽  
High Resolution Mass Spectrometry ◽  
X Ray ◽  
Moderate Yield ◽  
Resolution Mass

The 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine heterocyclic system has been used in the construction of heteropropellanes, which attracted much attention not only on the possible modification of drugs, but also for novel materials with unusual and important physical properties. In this communication, the reaction of ethyl 2-(hydroxyimino)propanoate 1 with disulfur dichloride and o-aminophenol, which gave ethyl 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate in moderate yield, was described. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy, mass-spectrometry and X-ray analysis.

scholarly journals Methyl (2E)-3-[3-Benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidin-1-yl]acrylate

Molbank ◽  
10.3390/m1176 ◽  
2020 ◽  
Vol 2021 (1) ◽  
pp. M1176
Author(s):  
Alexandra S. Golubenkova ◽  
Nikita E. Golantsov ◽  
Leonid G. Voskressensky
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
1H Nmr ◽  
13C Nmr ◽  
Title Compound ◽  
High Resolution Mass Spectrometry ◽  
Domino Reaction ◽  
Methyl Propiolate ◽  
Ft Ir ◽  
Resolution Mass

Compounds with propargylamine moiety are useful synthetic precursors of several important classes of nitrogen-containing heterocycles. The title compound, methyl (2E)-3-[3-benzyl-2-(3-methoxy-3-oxoprop-1-yn-1-yl)-2-(1-naphthyl)imidazolidine-1-yl]acrylate, has been prepared by domino-reaction, employing easily available 1-benzyl-2-(1-naphthyl)-4,5-dihydro-1H-imidazole and methyl propiolate in a high 92% yield. The structure of title compound was determined using 1H-NMR, 13C-NMR, UV, FT-IR and HRMS (High-Resolution Mass Spectrometry).

Nematicidal Activities of Diamides with Diphenylacetylene Scaffold Against Meloidogyne Incognita

2015 ◽  
Vol 68 (10) ◽  
pp. 1543 ◽  
Author(s):  
Jiling Li ◽  
Zhicheng Zhang ◽  
Xiaoyong Xu ◽  
Xusheng Shao ◽  
Zhong Li
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
High Activity ◽  
1H Nmr ◽  
13C Nmr ◽  
Meloidogyne Incognita ◽  
High Resolution Mass Spectrometry ◽  
The Novel ◽  
Low Toxicity ◽  
Resolution Mass

With the goal of searching for new potential nematicides with high activity and low toxicity, new molecules are needed as potential prototypes for the synthesis of new nematicidal compounds. A series of novel diamides based on diphenylacetylene scaffold were designed and synthesised. The conformation of the amide was restricted through the ten-membered H-bonded ring. Their structures were characterised by 1H NMR, 13C NMR, 19F NMR, and high-resolution mass spectrometry. The preliminary bioassays evaluated against Meloidogyne Incognita indicated that most of the title compounds were endowed with moderate-to-good activities at the concentration of 25 mg L–1. In particular, compounds 9a, 9c, 9g, 9h, 9k, and 9l displayed >50 % nematicidal activity at 5 mg L–1. It is possible that the novel diamides with diphenylacetylene scaffold, which possess good nematicidal activities, provide distinct nematicidal chemotypes that can be used as leads for further optimisation.

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

Molbank ◽  
10.3390/m1091 ◽  
2019 ◽  
Vol 2019 (4) ◽  
pp. M1091
Author(s):  
Vladimir A. Ogurtsov ◽  
Oleg A. Rakitin
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Good Yield ◽  
High Resolution Mass Spectrometry ◽  
Biologically Active ◽  
Active Compounds ◽  
Resolution Mass

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.

scholarly journals 7,7’-(4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole)

Molbank ◽  
10.3390/m1310 ◽  
2021 ◽  
Vol 2022 (1) ◽  
pp. M1310
Author(s):  
Nikita S. Gudim ◽  
Ekaterina A. Knyazeva ◽  
Oleg A. Rakitin
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Elemental Analysis ◽  
13C Nmr ◽  
High Resolution Mass Spectrometry ◽  
Uv Spectroscopy ◽  
Optoelectronic Devices ◽  
Cross Coupling ◽  
Resolution Mass ◽  
Ir And Uv Spectroscopy

2,6-Bis(benzo[c][1,2,5]thiadiazol-4-yl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophenes are of interest for the synthesis of molecules which can be employed in optoelectronic devices. In this communication, 7,7’-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole) was obtained by direct C–H cross-coupling of 4,7-dibromobenzo[c][1,2,5]thiadiazole with 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene in the presence of palladium(II)acetate and potassium pivalate. The structure of newly synthesized compound was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR and UV spectroscopy.

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