volume 56 issue 08 pages 1309-1323

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 typeJournal Article
Publication date2023-12-18
scimago Q2
wos Q2
SJR0.559
CiteScore4.6
Impact factor2.3
ISSN00397881, 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.
GOST all authors (up to 50) Copy
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 -
BibTex |
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BibTex (up to 50 authors) Copy
@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}
}
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.