Synthesis of 4-Ethoxycarbonyl(cyano)-β-Carbolines via Thermolysis of 4-Aryl-3(5)-Azidopyridine Derivatives and the Study of their Optical and Hypoglycemic Properties

Proshchenkova, Viktoriya А.; Shuvalov, Vladislav Yu.; Glyzdinskaya, Larisa V.; Fisyuk, A. S.; Черненко, Сергей А.; Хвостов, Михаил В.; Толстикова, Т. Г.; Воронцова, М. А.; Сагитуллина, Г. П.

doi:10.1007/s10593-021-02892-9

Cited by 3 publications

(2 citation statements)

References 22 publications

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“…To evaluate cytotoxicity and antiviral activity against influenza and vaccinia viruses, compounds 13a , b , d , 18a , b , f – h , and 24 , 19 25 19 were selected. The results are shown in Table 1 (see the SI for more details).…”

Section: Table 1 Cytotoxicity and Antiviral Activity Of...mentioning

confidence: 99%

Efficient Synthesis of Pyrido[3,4-c]cinnolines and Pyrido[3,2-c]cinnolines by Intramolecular Azo Coupling Reaction of 4,6-Diaryl-3-pyridine Diazonium Salts and Study of Their Antiviral Activity

Sagitullina,

Fisenko,

Shuvalov

et al. 2023

Synthesis

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A new method was proposed for the synthesis of pyrido[3,4-c]cinnolines and pyrido[3,2-c]cinnolines. Pyridine-3-diazonium tetrafluoroborates, containing donor methoxy groups in one of the aryl substituents, form pyridocinnolines at 0°C by intramolecular azo coupling reaction. The 2´-methoxy group in the aryl substituent of the pyridine-3-diazonium salt participates in the aromatic nucleophilic substitution reaction, which results in the elimination of the diazo group to form benzofuro[2,3-c]pyridine and benzofuro[3,2-b]pyridine. The intermediate and target reaction products were isolated in high yields.

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Section: Table 1 Cytotoxicity and Antiviral Activity Of...mentioning

confidence: 99%

Efficient Synthesis of Pyrido[3,4-c]cinnolines and Pyrido[3,2-c]cinnolines by Intramolecular Azo Coupling Reaction of 4,6-Diaryl-3-pyridine Diazonium Salts and Study of Their Antiviral Activity

Sagitullina,

Fisenko,

Shuvalov

et al. 2023

Synthesis

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“…Pyridazinoquinolines via diazotation, ring contraction and cyclization.2.2.2. Benzo Fused Tricyclic Derivatives Starting from PyridinesDiazotation of 4-aryl-3-aminopyridine derivatives 53 resulted in intramolecular electrophilic substitution of the very electron rich 3,4,5-trimethoxyphenyl substituent to afford the tricyclic pyrido[3,4-c]cinnolines 54 in 64-84% yield, similar to the Widman-Stoermer approach whereas for other less electron rich aryl groups the diazonium salt can be used without such cyclization to prepared azides, that then were thermolysed in xylene to carboline derivatives 55 (Scheme 12)[38].…”

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confidence: 99%

Synthetic Pathways to Pyrido[3,4-c]pyridazines and Their Polycyclic Derivatives

2022

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Pyrido[3,4-c]pyridazines are nitrogen-containing scaffolds that have been described as being promising in medicinal chemistry, but they are rather rare chemicals. In this review article, the literature on synthetic pathways towards pyrido[3,4-c]pyridazines is listed exhaustively, first with the bicyclic systems themselves that are obtained starting either from pyridines, pyridazines or other heterocycles. Then, the reports on the related tricyclic derivatives are discussed, again according to the source heterocycle, and finally we mention some examples on polycyclic systems.

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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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Synthesis of 4-Ethoxycarbonyl(cyano)-β-Carbolines via Thermolysis of 4-Aryl-3(5)-Azidopyridine Derivatives and the Study of their Optical and Hypoglycemic Properties

Cited by 3 publications

References 22 publications

Efficient Synthesis of Pyrido[3,4-c]cinnolines and Pyrido[3,2-c]cinnolines by Intramolecular Azo Coupling Reaction of 4,6-Diaryl-3-pyridine Diazonium Salts and Study of Their Antiviral Activity

Efficient Synthesis of Pyrido[3,4-c]cinnolines and Pyrido[3,2-c]cinnolines by Intramolecular Azo Coupling Reaction of 4,6-Diaryl-3-pyridine Diazonium Salts and Study of Their Antiviral Activity

Synthetic Pathways to Pyrido[3,4-c]pyridazines and Their Polycyclic Derivatives

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

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