Geometric Isomerism and DFT Theoretical Explanation of the Unexpected Formation of N, N-disubstituted Formamidines from 2-amino-3-cyano-4.6- diarylpyridines

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Author(s): El-sayed M Abdelrehim*, Doaa S El-Sayed

Journal Name: Current Chinese Chemistry

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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.

Keywords: Formamidines, Triflouroroacetic anhydride, syn/anti ratio, DFT calculations.

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(E-pub Ahead of Print)
DOI: 10.2174/2666001601666200123150220