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

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

Publication History

Received: 01 November 2023

Accepted: 14 December 2023

Accepted Manuscript online:
18 December 2023

Article published online:
24 January 2024

• 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