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.
Highlights
Introduction βEnaminones are an important building block for the synthesis of many compounds which have pharmacological features including antitumor [1,2], anti-inflammatory [3], anti-epileptic [4], anticonvulsant [5], antibacterial [6] and other therapeutic agents [7–9]
X-ray dif we describe a one-pot direct method single with high efficiency for β-enaminone synthesis viawere reaction of Hirshfeld analysis, DFT
The three targeted β-enaminones [1,2,3] were synthesized via an efficient onethe corresponding secondary amines in dioxane shown in Scheme 1
Summary
Introduction βEnaminones are an important building block for the synthesis of many compounds which have pharmacological features including antitumor [1,2], anti-inflammatory [3], anti-epileptic [4], anticonvulsant [5], antibacterial [6] and other therapeutic agents [7–9]. Many synthetic routes have been used for the synthesis of this special scaffold. Several catalysts such as InBr3 [15], vanadium (IV) acetylacetonate [16], LaCl3 [17], (CuI–2,20 -bipyridine–NaOtBu) [18], silica supported Fe(HSO4 ) under solvent free conditions [19], silver nanoparticles [20], and bimetallic. Have all all been employed in direct synthetic [21], have been employed in direct synthetim of dicarbonyl synthon with an amine to yield thethe β-enaminone. These reporte dicarbonyl synthon with an amine to yield β-enaminone. These repo been shown to have disadvantages, including low chemical yield, longer reaction ti been shown to have disadvantages, including low chemical yield, longer reaction in in thethe reaction work-up with low selectivity and no generality
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
