A1 Journal article (refereed)
One-Pot Synthesis, X-ray Single Crystal and Molecular Insight of Enaminone-Based β-Morpholino-/N-Methylpiperazinyl-/Pyrrolidinylpropiophenone (2020)


Barakat, A.; Soliman, S.M.; Haukka, M.; Al-Majid, A.M.; Islam, M.S.; Ali, M.; Shaik, M.R. (2020). One-Pot Synthesis, X-ray Single Crystal and Molecular Insight of Enaminone-Based β-Morpholino-/N-Methylpiperazinyl-/Pyrrolidinylpropiophenone. Crystals, 10 (4), 282. DOI: 10.3390/cryst10040282


JYU authors or editors


Publication details

All authors or editors: Barakat, A.; Soliman, S.M.; Haukka, M.; Al-Majid, A.M.; Islam, M.S.; Ali, M.; Shaik, M.R.

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2020

Volume: 10

Issue number: 4

Article number: 282

Publisher: MDPI

Publication country: Switzerland

Publication language: English

DOI: http://doi.org/10.3390/cryst10040282

Open Access: Publication published in an open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/68674


Abstract

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 °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 β-enaminones 1–3 were assigned by NMR. β-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…π 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.


Keywords: organic compounds; amines; chemical synthesis; x-ray crystallography

Free keywords: β-enaminone; DMFDMA; morpholine; N-methylpiperazine; pyrrolidine; Hirshfeld analysis


Contributing organizations


Ministry reporting: Yes

Reporting Year: 2020

Preliminary JUFO rating: 1


Last updated on 2020-18-08 at 13:48