Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones

Savchenko, Olga А.; Musiyak, Vera V.; Goncharov, D. S.; Bogza, Y. P.; Shatsauskas, Anton L.; Талзи, В. П.; Evdokimov, Sergey N.; Ulyankin, Evgeny B.; Fisyuk, A. S.

doi:10.1007/s10593-020-02795-1

Cited by 3 publications

(1 citation statement)

References 29 publications

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“…46 A similar behavior for 2-pyridones has been reported by us earlier. 47 When the proton exchange rate is high, an averaged signal of two tautomeric forms is observed in the NMR spectra. Both forms can be detected at low rate.…”

Section: Paper Synthesismentioning

confidence: 99%

Easy Route to New Fused Dihydroisoquinoline-Naphthyridinone Frameworks

Fisyuk

Shuvalov

2022

Synthesis

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The reaction of 1-methyl-3,4-dihydroisoquinolines with azlactone, obtained from hippuric acid and phthalic anhydride, provided 2-(3-benzamido-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinolin-2-yl)benzoic acids, which were converted into previously unknown 9,10-dihydro-6H-benzo[c]isoquinolino[1,2-g][1,7]naphthyridine-5,7-diones by the action of hydrazine hydrate. Further reaction of the prepared naphthyridine-5,7-diones with POCl3 under various conditions led to the formation of 5-chloro-9,10-dihydro-7H-benzo[c]isoquinolino[1,2-g][1,7]naphthyridin-7-one or 4,6-dichloro-2-(2-(2-methylprop-1-en-1-yl)phenyl)benzo[c][1,7]naphthyridine. It was shown that the halogen atom in the C-5 position enters into a substitution reaction with primary and secondary amines.

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Section: Paper Synthesismentioning

confidence: 99%

Easy Route to New Fused Dihydroisoquinoline-Naphthyridinone Frameworks

Fisyuk

Shuvalov

2022

Synthesis

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New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

Fisyuk,

Shuvalov,

Shatsauskas

et al. 2023

Synthesis

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Reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole with azlactones under solvent-free conditions with heating furnished tetrahydro-1H-pyrazolo[3,4-b]pyridines. The latter were converted to oxazolo[5,4-b]pyrazolo[4,3-e]pyridines by the action with POCl3 on air. Further reaction of oxazolo[5,4-b]pyrazolo[4,3-e]pyridines with hydrazine hydrate and alkali led to the formation of 5-amino-1,7-dihydro-6H-pyrazolo[3,4-b]pyridin-6-ones, which reacted with aluminum chloride to yield 3,4-dihydro-5H-pyrazolo[4,3-f][1,7]naphthyridin-5-ones. Some of the synthesized compounds show antioxidant activity or are effective phosphors.

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