Autoxidation of 4-Hydrazinylquinolin-2(1 H)-one; Synthesis of Pyridazino[4,3- c:5,6- c']diquinoline-6,7(5 H,8 H)-diones

Sara M Mostafa; Ashraf A Aly; Alaa A Hassan; Esraa M Osman; Stefan Bräse; Martin Nieger; Mahmoud A A Ibrahim; Asmaa H Mohamed

doi:10.3390/molecules27072125

Autoxidation of 4-Hydrazinylquinolin-2(1 H)-one; Synthesis of Pyridazino[4,3- c:5,6- c']diquinoline-6,7(5 H,8 H)-diones

Molecules. 2022 Mar 25;27(7):2125. doi: 10.3390/molecules27072125.

Authors

Sara M Mostafa¹, Ashraf A Aly¹, Alaa A Hassan¹, Esraa M Osman¹, Stefan Bräse^{2

3}, Martin Nieger⁴, Mahmoud A A Ibrahim¹, Asmaa H Mohamed¹

Affiliations

¹ Chemistry Department, Faculty of Science, Minia University, El Minia 61519, Egypt.
² Institute of Organic Chemistry, Karlsruhe Institute of Technology, Eggenstein-Leopoldshafen, 76131 Karlsruhe, Germany.
³ Institute of Biological and Chemical Systems (IBCS-FMS), Karlsruhe Institute of Technology, Eggenstein-Leopoldshafen, 76131 Karlsruhe, Germany.
⁴ Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio I), 00014 Helsinki, Finland.

Abstract

An efficient synthesis of a series of pyridazino[4,3-c:5,6-c']diquinolines was achieved via the autoxidation of 4-hydrazinylquinolin-2(1H)-ones. IR, NMR (¹H and ¹³C), mass spectral data, and elemental analysis were used to fit and elucidate the structures of the newly synthesized compounds. X-ray structure analysis and theoretical calculations unequivocally proved the formation of the structure. The possible mechanism for the reaction is also discussed.

Keywords: 4-hydrazinylquinolin-2(1H)-one; DFT; X-ray; autoxidation reaction; pyridazino[4,3-c:5,6-c′]diquinoline-6,7(5H,8H)-dione.