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. 2022 Mar 25;27(7):2125.
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

Sara M Mostafa  1 , Ashraf A Aly  1 , Alaa A Hassan  1 , Esraa M Osman  1 , Stefan Bräse  2   3 , Martin Nieger  4 , Mahmoud A A Ibrahim  1 , Asmaa H Mohamed  1
Affiliations

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 et al. Molecules. .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of biologically active Pyridazomycin, Minaprine, Pyridaben and Chloridazone.
Scheme 1
Scheme 1
Formation of compound 3a from the reaction of 1-ethyl-4-hydroxyquinolin-2(1H)-one (1) with hydrazine in o-DCB.
Scheme 2
Scheme 2
Synthesis of pyridazino[4,3-c:5,6-c′]diquinoline-6,7(5H,8H)-diones 3a–g. Reagents and conditions: (a) POCl3, reflux, 2 h; (b) AcOH, reflux 12 h; (c) NH2.NH2.H2O, reflux 12 h; (d) pyridine reflux, 6–12 h.
Figure 2
Figure 2
Molecular structure of one of the crystallographic independent molecules of 3a.
Scheme 3
Scheme 3
The suggested mechanism describes the formation of compounds 3a–g.
Figure 3
Figure 3
The assigned structure of compound 3a.
Figure 4
Figure 4
(a) Quantum theory of atoms in molecules (QTAIM) and (b) 3D noncovalent interaction (NCI) isosurfaces for compound 3a. The isosurfaces were generated with a reduced density gradient value of 0.50 au and colored from blue to red according to sign (λ2), ρ ranging from −0.035 (blue) to 0.020 (red) au.
See this image and copyright information in PMC

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