Heterocyclic compounds were prepared from Schiff bases triester derivatives, the first step was included, p- aminobenzoic acids convert to p-amino benzoyl chloride in the presence of thionyl chloride then glycerol was added to form triesters compound A. second step reaction of triester product with the 4-nitrobenzaldehyde, and 3-amino benzaldehyde to produce M1, and M2. The third step. Involve reacted Schiff bases triester derivatives to give heterocyclic compounds M1S, M1A, M2P, and M2K. The structure of all compounds is monitored by (TLC), and identified by many techniques 1HNMR, FT-IR, and melting point.
Abstract
The present study included the synthesis of two series of heterocyclic compounds, azetidin-2-one and 1,3-oxazepine derivatives. All synthesized compounds were characterized using FT-IR and 1H NMR spectra. The study was divided into two parts. The first synthesis Schiff bases derivatives (1-4) via the condensation reaction of 1,1′-biphenyl-4,4′-diamine (A) with benzaldehyde derivatives (2,5-dimethoxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, furan-2-carbaldehyde and 3-hydroxybenzaldehyde). The second synthesis azetidine-2-one derivatives (5-8) from the reaction of Schiff bases with chloroacetyl chloride. Schiff bases also reacted with maleic anhydride to yield 1,3-oxazepine derivatives (9-12).
This study including prepared new colored esters containing heterocyclic with high molecular weights. In the first part of work we synthesized azo dyes [1,2] from the reaction p-toluidine with β-naphthol and o-nitro phenol, thin we synthesized Schiff bases [3,4] by the reaction anthranilic acid with benzaldehyde and dimethyl benzaldehyde. The reaction azo dyes (contain OH group) with Schiff base (contain COOH group) these led to produce the new colored esters [A1-A4]. The second part of work was modification the (C=N-) group in esters to heterocyclic compounds by reacting with phenyl iso cyanide to produce new β-lactam [B1-B4] and with anthranilic acid to get new hydroquinazoline [C1-C4]. All these compounds were characterized by physical properties and spectral methods FTIR, 1H-NMR and 13C-NMR.
Synthesis and characterization of azetidin-2-one and 1,3-oxazepine derivatives using Schiff bases derived from 1,1’-biphenyl-4,4’-diamine