Journal
CRYSTALS
Volume 10, Issue 4, Pages -Publisher
MDPI
DOI: 10.3390/cryst10040282
Keywords
beta-enaminone; DMFDMA; morpholine; N-methylpiperazine; pyrrolidine; Hirshfeld analysis
Funding
- King Saud University, Riyadh, Saudi Arabia [RSP-2019/64]
Ask authors/readers for more resources
One-pot synthesis of three enaminones, (E)-1-(4-chlorophenyl)-3-morpholinoprop-2-en-1-one 1, (E)-1-(4-chlorophenyl)-3-(4-methylpiperazin-1-yl)prop-2-en-1-one 2, and (E)-1-(4-chlorophenyl)-3-(pyrrolidin-1-yl)prop-2-en-1-one 3 were achieved. The synthetic protocol via three components reaction of p-chloroacetophenone with DMFDMA (N,N-dimethylformamid-dimethylacetal) and the corresponding secondary amines (morpholine/N-methylpiperazine/pyrrolidine) in dioxane under heating for 2.5-4 h at 102 degrees C yielded the requisite enaminones. This protocol has the advantage of no separation of intermediate, no need for column purification with quantitative yield for the target compounds. The chemical features of the beta-enaminones 1-3 were assigned by NMR. beta-Enaminones 1, and 2 were assigned by single crystal X-ray diffraction technique. The intermolecular interactions in the crystal structures were analyzed quantitatively using Hirshfeld analysis. The Cl...H and O...H hydrogen bonds are common in both compounds while the C-H...pi and N...H contacts are more significant in 2 than 1. DFT studies were investigated to show the electronic and spectroscopic properties (NMR and UV-Vis) of the studied systems.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available