A regioselective synthesis has been developed for the preparation of a series of N,N'-disubstituted 4,4'-carbonylbis(carbamoylbenzoic) acids and N,N'-disubstituted bis(carbamoyl) terephthalic acids by treatment of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (1) and 1,2,4,5-benzenetetracarboxylic dianhydride (2) with arylalkyl primary amines (A-N). The carbamoylcarboxylic acid derivatives were synthesized with good yield and high purity. The specific reaction conditions were established to obtain carbamoyl and carboxylic acid functionalities over the thermodynamically most favored imide group. Products derived from both anhydrides 1 and 2 were isolated as pure regioisomeric compounds under innovative experimental conditions. The chemo- and regioselectivity of products derived from dianhydrides were determined by NMR spectroscopy and confirmed by density functional theory (DFT). All products were characterized by NMR, FTIR, and MS.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3913102PMC
http://dx.doi.org/10.1155/2014/725981DOI Listing

Publication Analysis

Top Keywords

regioselective synthesis
8
products derived
8
novel highly
4
highly regioselective
4
synthesis carbamoylcarboxylic
4
carbamoylcarboxylic acids
4
acids dianhydrides
4
dianhydrides regioselective
4
synthesis developed
4
developed preparation
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!