A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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), Article 282. https://doi.org/10.3390/cryst10040282

JYU-tekijät tai -toimittajat

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Barakat, A.; Soliman, S.M.; Haukka, M.; Al-Majid, A.M.; Islam, M.S.; Ali, M.; Shaik, M.R.

Lehti tai sarja: Crystals

eISSN: 2073-4352

Julkaisuvuosi: 2020

Volyymi: 10

Lehden numero: 4

Artikkelinumero: 282

Kustantaja: MDPI

Julkaisumaa: Sveitsi

Julkaisun kieli: englanti

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

Julkaisun avoin saatavuus: Avoimesti saatavilla

Julkaisukanavan avoin saatavuus: Kokonaan avoin julkaisukanava

Julkaisu on rinnakkaistallennettu (JYX): https://jyx.jyu.fi/handle/123456789/68674

Tiivistelmä

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.

YSO-asiasanat: orgaaniset yhdisteet; amiinit; kemiallinen synteesi; röntgenkristallografia

Vapaat asiasanat: β-enaminone; DMFDMA; morpholine; N-methylpiperazine; pyrrolidine; Hirshfeld analysis

Liittyvät organisaatiot

OKM-raportointi: Kyllä

Raportointivuosi: 2020

JUFO-taso: 1