Synthesis Of New Asymmetrical Pyromellitdiimides Derived From Pyromellitic Dianhydride

Abstract

This work involves the synthesis and characterization of asymmetrical pyromellitdiimide
derivatives [IV]a-f
by four sequence steps selective reaction . One mole of pyromellitic dianhydride
was reacted with one mole of various primary aromatic amines [ 4-nitro aniline , 4-chloro aniline , 4-toludine and 4-anisidine] in excess of dry acetone to produce six compounds (N-substituted-pyromellitamic monoacid) [I]a-f . These new compounds [I]a-d were converted to the corresponding
N- substituted- pyromellitmonoimide [II]a-d via their heating at (80-90)
0
C in sodium acetate-acetic
anhydride mixture .
The compounds [II]a-f
were allowed to react with one mole of another primary amines in
excess of dry acetone to give new derivatives of amic acid [II]a-d followed by intramolecular
cyclization reaction of these compounds [IV]a-f in sodium acetate-acetic anhydride system to yield the
desired asymmetrical pyromellitdiimide derivatives [IV]a-f
, the above reactions can be summarized in
Scheme 1.
All the synthesized compounds have been studied and charachterized by their melting points
, FTIR , and
1
HNMR spectroscopy (for some of them)