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
Publication type: Journal Article
Publication date: 2023-12-18
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A new method is 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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Sagitullina G. P. et al. 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 // Synthesis. 2023. Vol. 56. No. 08. pp. 1309-1323.
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Sagitullina G. P., Fisenko A. Y., Shuvalov V. Y., Arshinov E. V., Glizdinskaya L. V., Shishkina L. N., Bormotov N. I., Serova O. A. 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 // Synthesis. 2023. Vol. 56. No. 08. pp. 1309-1323.
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TY - JOUR
DO - 10.1055/a-2230-0583
UR - http://www.thieme-connect.de/DOI/DOI?10.1055/a-2230-0583
TI - 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
T2 - Synthesis
AU - Sagitullina, Galina P.
AU - Fisenko, Alina Yu.
AU - Shuvalov, Vladislav Yu.
AU - Arshinov, Evgenii V
AU - Glizdinskaya, Larisa V
AU - Shishkina, Larisa N.
AU - Bormotov, Nikolay I.
AU - Serova, Olga A.
PY - 2023
DA - 2023/12/18
PB - Georg Thieme Verlag KG
SP - 1309-1323
IS - 08
VL - 56
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2023_Sagitullina,
author = {Galina P. Sagitullina and Alina Yu. Fisenko and Vladislav Yu. Shuvalov and Evgenii V Arshinov and Larisa V Glizdinskaya and Larisa N. Shishkina and Nikolay I. Bormotov and Olga A. Serova},
title = {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},
journal = {Synthesis},
year = {2023},
volume = {56},
publisher = {Georg Thieme Verlag KG},
month = {dec},
url = {http://www.thieme-connect.de/DOI/DOI?10.1055/a-2230-0583},
number = {08},
pages = {1309--1323},
doi = {10.1055/a-2230-0583}
}
Cite this
MLA
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Sagitullina, Galina P., et al. “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.” Synthesis, vol. 56, no. 08, Dec. 2023, pp. 1309-1323. http://www.thieme-connect.de/DOI/DOI?10.1055/a-2230-0583.
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