The scheme of this work involves synthesis of p-N,N-dimethylamino benzylideneareneamines (Schiff bases). Compounds (N2-N17) were synthesized by condensation of p-N,N-dimethylaminobenzaldehyde with different primary aromatic amines in the presence of absolute ethanol with reflux for (2) hrs to produce sixteen derivatives of Schiff bases. This work is divided to four different parts scheme(I):
To obtain oxazepine derivatives (N18-N33) and (N34-N49), Schiff bases (N2-N17) were reacted with maleic anhydride in the presence of dry benzene with reflux for (3) hrs to produce sixteen derivatives of oxazepine compounds (N18-N33) and also reacted with phthalic anhydride to produce other sixteen oxazepine compounds (N34-N49)which are 2-(p-N,N-dimethylaminobenzyl) -3-aryl -2,3-dihydro benz [1,2-e] [1,3] –oxazepine – 4,7- diones, the resulting colored crystalline solid was recrystallized form dry 1, 4-dioxan scheme (I).
This part involves the synthesis of diazepine derivatives [N50-N54] . Oxazepine derivatives [N35, N38, N41, N46, N48] were reacted with various primary aromatic amines in dry benzene with reflux for (4-5)hrs to produce five derivatives of diazepine compounds of 1-(aryl)-2-(p-N,N-dimethyl amino benzyl) -3 - aryl - 1,2,3 - trihydro benzo [1,2,3] [1,3] – diazepine - 4,7 -diones [N50-N54] the resulting colored crystalline solid was recrystallized from ethanol scheme (I).
This part involves the thio derivatives of open ring [N55-N58] by the reaction of oxazepine derivatives [N18, N19, N21, N31] were reacted with benzene thiol or with 2-mercapto benzene thiazol in dry benzene with reflux for (4-5) hrs to the four derivatives of thio compounds of N-(p-N,N-dimethy (amino benzyl alcohol)- N-(4-benzo thiazol sulphide) -1.4 – done – 2- butane) –N-aryl amine [N55-N58].The resulting colored crystalline solid was recrystallized from ethanol.
The attempt to synthesis thiazepine compounds by using oxazepine compounds was failed.
The Schiff bases [N2-N17] , oxazepines [N18-N33] , oxazepines [N34-N49] , diazepines [N50-N54] , open chain thio derivatives [N55-N58] , have been characterized by melting points, C.H.N Analysis and spectroscopic methods (Uv-Vis, FT.IR, HN.M.R), this work is summarized by the following scheme(I):
Cite this article:
Nagham Mahmood Al-jamali. Synthesis and Characterization of New 1,3- Oxazepine, Diazepine, thiazepine Derivatives and Open Ring of Thio compounds. ian J. Research Chem. 7(12): December, 2014; Page 1067-1104.