Title:Geometric Isomerism and DFT Theoretical Explanation of the Unexpected Formation of N, N-disubstituted Formamidines from 2-amino-3-cyano-4.6- diarylpyridines
VOLUME: 1
Author(s):El-sayed M Abdelrehim* and Doaa S El-Sayed
Affiliation:Chemistry department, Faculty of science, Damanhour University, Damanhur, Chemistry department, Faculty of science, Alexandria University, Alexandria
Keywords:Formamidines, Triflouroroacetic anhydride, syn/anti ratio, DFT calculations.
Abstract:Aims: A new method for synthesis of N,N-disubstituted formamidines were obtained
upon the reaction of 2-amino-3-cyano-4.6-diarylpyridines with triflouroroacetic anhydride (TFAA)
in dimethyl formamide (DMF)
Background: Continuing our interesting to the study the modification of the amino group present
in 2-amino-3-cyano-4.6-diarylpyridines references:- 1. Elsaedany, S.K.; Zein M. A.; Abdelrehim
E.M.; Keshk R. M. J.Hetrocyclic Chem.2016.53, 1534. 2. Abdelrehim E.M.; Zein M. A.
J.Hetrocyclic Chem.2018.55, 419.
Objective: Synthesis of N,N-disubstituted formamidines series and suggest the mechanism of the
reaction
Method: Methods of preparation of organic compounds, of spectral analysis of prepared
compounds and DFT calculations using the B3LYP functional and 6-311G (p,d) basis set to
suggest the reaction mechanism of formamidine formation
Results: prove the structure of synthesized compounds.and suggest the reaction mechanism of
formamidine formation
Conclusion: In this work there was no pre-planned preparation of a series of N,N-disubstituted
formamides in the presence of TFAA but it was an unexpected product as well as the products
have different geometric isomers which confirmed using DFT calculations using the B3LYP
functional and 6-311G(p,d) basis set. It is clear that DMF is not the appropriate solvent in the case
of preparation of triflouroacetamide.
Other: In this work there was no pre-planned preparation of a series of N,N-disubstituted
formamides in the presence of TFAA.
