Synthesis, identification of some new derivatives of 4-amino antipyrine bearing six and seven membered rings

Abstract

In this paper, we consider the Synthesis of a series of various 4-amino antipyrine derivatives containing 1,3-thiazinan-4-one, 1,3-oxazinan-6-one, and 1,3-oxazepin-4,7-dione in its structure. These derivatives were obtained via cycloaddition of the methenamine group in Schiff base analog of 4-amino antipyrine with 3-mercaptopropanoic acid, 3-chloropropanoic acid, maleic and citraconic anhydride, respectively. The Schiff bases were prepared in excellent yields by condensation of 4-amino antipyrine with 3-nitro- or 3-bromobenzaldehyde in n-butanol. We characterize the desired products by C.H.N.S analysis, FT-IR, and 1HNMR spectroscopy.

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“…Many signals indications at δ 7.83-7.77 ppm are the result of twelve aromatic protons. Finally, the 1 H-NMR spectrum reveals two peaks at δ 6.06 and 6.04 and δ 7.05 ppm that could be identical to CH=CH ring of oxazepine ring and one proton of CH-N group [11,12]. The 1 H-NMR spectrum (DMSO-d6), of compounds (III) showed a sharp signal at δ 3.34 ppm for one proton of diazepine group (N-CH-N), doublet signal at δ 6.29 and 6.11 ppm for two protons of CH=CH and twelve aromatic protons appear at the range δ 7.83-7.54 ppm.…”

Synthesis, Characterization of New Ligand Derived from 4-aminoantipyrine and its Complexes with Few Metallic Ions and Evaluation of their Activity as Anticancer

“…The spectrum of the free ligand showed two clear bands at (3409 and 3379 cm -1 ), which belong to the hydroxyl υ(OH) and secondary amine groups υ(NH), respectively. 33 A band appeared in the spectrum of the ligand at (1681 cm -1 ), an important band whose appearance indicates the formation of the ligand, which is the azomethine group (C = N) that belongs to the schiff base, 34 while the carbonyl group band in the reactants before the reaction disappears. Other bands appeared in (3078 cm -1 ) and (2962 and 2893 cm -1 ), which belong to the (C-H) aromatic and aliphatic groups, respectively, 35 as for the groups (C=C) aromatic, it gave bands at (1496, 1573 cm -1 ), finally, other bands exhibited at (1596, 1010 cm -1 ) due to the functional groups υ (C = N) and (C-S) of the benzothiazole ring, respectively (Figure 2).…”