One-step synthesis of 3-cyano-6-methyl-4-thienyl-5,6,7,8-tetrahydro[1,6]naphthyridine-2(1H)-thiones and annelated heterocyclic systems on their basis

Shestopalov, Alexander A.; Gromova, Anna V.; Rodinovskaya, L. A.; Nikishin, K. G.; Литвинов, В. П.; Шестопалов, А. М.

doi:10.1007/s11172-005-0133-7

Cited by 10 publications

(7 citation statements)

References 3 publications

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“…The starting compounds for the synthesis of the desired heterocycles, 6-methyl-1,2,5,6,7,8-hexahydro-2-thioxo-1,6naphthyridine-3-carbonitrile (3a) and its 2'-thienyl derivative (3b) were prepared by reacting the sodium salt of 3-formyl-1-methyl-4-piperidone with cyanothioacetamide 21 and thienylidene-cyanothioacetamide with 1-methyl-4-piperidone 22 , respectively (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of thieno[2,3-b][1,6]naphthyridines and pyrimido[4′,5′:4,5] thieno[2,3-b][1,6]naphthyridines

Abdel-Wadood

Abdel-Monem

Fahmy

et al. 2008

Journal of Chemical Research

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3- 6,7,6]naphthyridine-2(1H)-thione (3a) and 3-cyano-6-methyl-4-(2'-thienyl)-5,6,7,8tetrahydro[1,6]naphthyridine-2(1H)-thione (3b) were reacted with a-halo compounds to give the intermediates 4a-j which upon refluxing in ethanolic sodium ethoxide afforded the thieno [2,3-b][1,6]naphthyridine derivatives 5a-l. Further annellation of pyridine and pyrimidine rings to the remaining free bond of the fused thiophene ring was achieved, providing tetrahydro-pyrido [2',3':4,5]-and -pyrimido[4',5':4,5]-thieno[2,3-b][1,6]naphthyridines. Some of the synthesised compounds were screened against different strains of bacteria.

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Section: Resultsmentioning

confidence: 99%

“…6-Methyl-1,2,5,6,7,8-hexahydro-2-thioxo-1,6-naphthyridine-3carbonitrile (3a) 21 and its 4-(2-thienyl) analogue (3b) 22 were prepared following literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of thieno[2,3-b][1,6]naphthyridines and pyrimido[4′,5′:4,5] thieno[2,3-b][1,6]naphthyridines

Abdel-Wadood

Abdel-Monem

Fahmy

et al. 2008

Journal of Chemical Research

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“…[38] The mass spectrum of 7 gave a molecular ion peak at m/ z = 381. [39] The IR spectrum of 9 shows the presence of NH and CN groups at ύ 3380 and 2220 cm −1 . Its 1 H NMR spectrum revealed four singlet signals at δ 6.13, 8.24, 11.56, and 12.18 ppm assigned to piperonal-CH 2 , pyridine-H and two pyrimidine-NH protons, respectively, in addition to six aromatic protons in the range of δ 7.09 to 7.89 ppm (see experimental section).…”

Section: Chemistrymentioning

confidence: 96%

Efficient synthesis and molecular docking of novel antibacterial pyrimidines and their related fused heterocyclic derivatives

Sanad

Ahmed

Mekky

2019

Journal of Heterocyclic Chem

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3-(Benzo[d] [1,3]dioxol-5-yl)-1-(thiophen-2-yl)prop-2-en-1-one reacted with each of thiourea and 6-amino-2-thioxo-2,3-dihydropyrimidin-4(1H)-one to give the corresponding pyrimidine-2(1H)-thiones. Then, these compounds reacted with the appropriate hydrazonyl chlorides in dioxane in the presence of triethylamine to afford the corresponding [1,2,4]triazolo[4,3-a]pyrimidines and their related fused pyridines. Moreover, chalcone was cyclocondensed with 2-cyanothioacetamide to give pyridine-2(1H)-thione and taken as a key synthon to novel 2-(methylthio)pyridothienopyrimidin-4(3H)-one derivative. The above derivative reacted with the appropriate hydrazonyl chlorides in dioxane in the presence of triethylamine to yield the corresponding pyridothieno[3,2-d][1,2,4]triazolo[4,3-a]pyrimidines. Study of the in vitro antimicrobial activities of the newly pyrimidines were performed. Pyridothienopyrimidine 24a showed the highest inhibitory activity against all bacteria with MIC values of 3.9, 7.81, 7.81, and 15.62 μg/mL, respectively, against Escherichia coli, Klebsiella pneumonia, Staphylococcus aureus, and Streptococcus mutans, respectively, as compared to reference drugs. Molecular docking was studied to predict of the optimized conformation of pyrimidines as active ligands against the Escherichia coli alkaline phosphatase. The structures of the hybrid molecules were elucidated by IR, Mass, 1 H NMR, and 13 C NMR spectra as well as elemental analyses.

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“…Pyridine‐2(1 H )‐thiones 485 were synthesized in one step by the reaction of elemental sulfur, malononitrile 325 , and chalcones 484 in the presence of a slight excess of triethylamine as sulfur activator (Scheme ) . The ketonitrile 486 initially formed from chalcone 484 and dinitrile 325 , is thiolated at the most activated methine position by trimethylamine‐sulfur complex 487 to afford thiol 488 .…”

Section: Sulfur As Building Block – Sulfuration Reactionsmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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Elemental sulfur hasb een known since Antiquity and found widespread applications in the preparation of black gunpowder,t he synthesis of sulfuric acid as well as other sulfur-containing compounds,a nd the vulcanization of rubber.O ver the last several years,wehave come to better understand its properties andd iscover more applications of elementals ulfuri ns ynthetic organic chemistry.T his review summarizes the advancesf rom 2000i nt he construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

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One-step synthesis of 3-cyano-6-methyl-4-thienyl-5,6,7,8-tetrahydro[1,6]naphthyridine-2(1H)-thiones and annelated heterocyclic systems on their basis

Cited by 10 publications

References 3 publications

Synthesis of thieno[2,3-b][1,6]naphthyridines and pyrimido[4′,5′:4,5] thieno[2,3-b][1,6]naphthyridines

Synthesis of thieno[2,3-b][1,6]naphthyridines and pyrimido[4′,5′:4,5] thieno[2,3-b][1,6]naphthyridines

Efficient synthesis and molecular docking of novel antibacterial pyrimidines and their related fused heterocyclic derivatives

Recent Advances in Organic Reactions Involving Elemental Sulfur

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