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

Alina Yu. Fisenko; Vladislav Yu. Shuvalov; Evgenii V. Arshinov; Larisa V. Glizdinskaya; Larisa N. Shishkina; Nikolay I. Bormotov; Olga A. Serova; Galina P. Sagitullina

doi:10.1055/a-2230-0583

Synthesis, Table of Contents

Synthesis 2024; 56(08): 1309-1323
DOI: 10.1055/a-2230-0583

paper

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

Alina Yu. Fisenko

^aDepartment of Organic and Analytical Chemistry, F. M. Dostoevsky Omsk State University, 55a Mira Ave., 644077 Omsk, Russian Federation

,

Vladislav Yu. Shuvalov

^bLaboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave., 644050 Omsk, Russian Federation

,

Evgenii V. Arshinov

^aDepartment of Organic and Analytical Chemistry, F. M. Dostoevsky Omsk State University, 55a Mira Ave., 644077 Omsk, Russian Federation

,

Larisa V. Glizdinskaya

^aDepartment of Organic and Analytical Chemistry, F. M. Dostoevsky Omsk State University, 55a Mira Ave., 644077 Omsk, Russian Federation

,

Larisa N. Shishkina

^cState Research Center of Virology and Biotechnology “VECTOR”, Novosibirsk Region, 6300559 Koltsovo, Russian Federation

,

Nikolay I. Bormotov

^cState Research Center of Virology and Biotechnology “VECTOR”, Novosibirsk Region, 6300559 Koltsovo, Russian Federation

,

Olga A. Serova

^cState Research Center of Virology and Biotechnology “VECTOR”, Novosibirsk Region, 6300559 Koltsovo, Russian Federation

,

Galina P. Sagitullina ∗

^aDepartment of Organic and Analytical Chemistry, F. M. Dostoevsky Omsk State University, 55a Mira Ave., 644077 Omsk, Russian Federation

› Author Affiliations

Abstract

All articles of this category

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.

Key words

azo coupling reaction - 3-aminopyridine - benzofuro[2,3-c]pyridine - benzofuro[3,2-b]pyridine - pyrido[3,4-c]cinnoline - pyrido[3,2-c]cinnoline

Full Text

References

References
1 Ball CJ, Gilmore J, Willis MC. Angew. Chem. Int. Ed. 2012; 51: 5718
2 Zhang G, Miao J, Zhao Y, Ge H. Angew. Chem. Int. Ed. 2012; 51: 8318
3 Shi Y, Bin Z, Liu J, Han W, Yang G, Lei B, You J. Angew. Chem. Int. Ed. 2022; 61: e202202898
4 Huang J, Gallucci JC, Turro C. Chem. Sci. 2020; 11: 9775
5 Sienkowska MJ, Farrar JM, Zhang F, Kusuma S, Heiney PA, Kaszynski P. J. Mater. Chem. 2007; 17: 1399
6 Takeda Y, Okazaki M, Minakata S. Chem. Commun. 2014; 50: 10291
7 Pan C, Yuan C, Chen D, Chen Y, Yu J.-T. Asian J. Org. Chem. 2022; 11: e202100809
8 Vinogradova OV, Balova IA. Chem. Heterocycl. Comp. 2008; 44: 501
9 The Chemistry of Heterocyclic Compounds, Cinnolines and Phthalazines, Supplement II, Chemistry of Heterocyclic Compounds: A Series of Monographs, Vol. 64. Brown DJ, Ellman JA, Taylor EC. Wiley; New York: 2005
10 Barton JW, Walker RB. Tetrahedron Lett. 1975; 569
11 Slevin A, Koolmeister T, Scobie M. Chem. Commun. 2007; 2506
12 Amer AM, El-Bermaui MA, Ahmed AF. S, Soliman SM. Monatsh. Chem. 1999; 130: 1409
13 Iqbal J, Gupta A, Husain A. Pharmazie 2006; 61: 747
14 Sizova EE, Arshinov EV, Kotsareva YA, Glizdinskaya LV, Sagitullina GP. Chem. Heterocycl. Comp. 2017; 53: 1026
15 Shuvalov VYu, Elisheva VA, Belousova AS, Arshinov EV, Glizdinskaya LV, Chernenko SA, Fisyuk AS, Sagitullina GP. Chem. Heterocycl. Comp. 2020; 56: 73
16 Yue WS, Li JJ. Org. Lett. 2002; 4: 2201
17 Gonzales JP, Edgar M, Elsegood MR. J, Weaver GW. Org. Biomol. Chem. 2011; 9: 2294
18 Lai L-Li, Lin P-Y, Huang W-H, Shiao M-J, Hwu JR. Tetrahedron Lett. 1994; 35: 3545
19 Proshchenkova V. А, Shuvalov VYu, Glyzdinskaya LV, Fisyuk AS, Chernenko SA, Khvostov MV, Tolstikova TG, Vorontsova M. А, Sagitullina GP. Chem. Heterocycl. Compd. 2021; 57: 187
20 Voronina TA, Guzeevatykh LS, Mironov AN. Guidelines for Conducting Preclinical Studies of Drugs, Part 1. . Mulyar AG, Chichenkov ON. Grif and K; Moscow: 2012: 944

21a Shuvalov VYu, Rupp AS, Kuratova AK, Fisyuk AS, Nefedov AA, Sagitullina GP. Synlett 2019; 30: 919
21b Shuvalov VYu, Shestakov AN, Kulakova LA, Kuratova AK, Vorontsova MA, Sagitullina GP. Chem. Heterocycl. Compd. 2019; 55: 844
21c Shuvalov VYu, Rupp AS, Fisyuk AS, Kuratova AK, Nefedov AA, Sagitullina GP. ChemistrySelect 2019; 4: 1696
21d Agarwal PK, Dathi MD, Saifuddin M, Kundu B. Beilstein J. Org. Chem. 2012; 8: 1901

22a Nazar MF, Badshah A, Mahmood A, Zafar MN, Janjua MR. S. A, Raza MA, Hussain R. J. Phys. Org. Chem. 2016; 29: 152
22b Umareddy P, Arava VR. Synth. Commun. 2016; 46: 309
22c Batt DG, Goodman R, Jones DG, Kerr JS, Mantegna LR, McAllister C, Newton RC, Nurnberg S, Welch PK, Covington MB. J. Med. Chem. 1993; 36: 1434
22d Şahin ZS, Salgin-Gökşen U, Gökhan-Kelekçi N, Işik Ş. J. Mol. Struct. 2011; 1006: 147

23a Parida C, Maity R, Chandra Sahoo S, Chandra Pan S. Org. Lett. 2019; 21: 6700
23b Troschütz R. Arch. Pharm. (Weinheim) 1989; 322: 285

Supplementary Material

Supporting Information