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- Title
Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis.
- Authors
Aljohani, Ghadah; Said, Musa A.; Lentz, Dieter; Basar, Norazah; Albar, Arwa; Alraqa, Shaya Y.; Ali, Adeeb Al-Sheikh; Spencer, John
- Abstract
An efficient microwave-assisted one-step synthetic route toward Mannich bases is developed from 4-hydroxyacetophenone and different secondary amines in quantitative yields, via a regioselective substitution reaction. The reaction takes a short time and is non-catalyzed and reproducible on a gram scale. The environmentally benign methodology provides a novel alternative, to the conventional methodologies, for the synthesis of mono- and disubstituted Mannich bases of 4-hydroxyacetophenone. All compounds were well-characterized by FT-IR, 1H NMR, 13C NMR, and mass spectrometry. The structures of 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one (2a) and 1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}ethan-1-one (3a) were determined by single crystal X-ray crystallography. Compound 2a and 3a crystallize in monoclinic, P21/n, and orthorhombic, Pbca, respectively. The most characteristic features of the molecular structure of 2a is that the morpholine fragment adopts a chair conformation with strong intramolecular hydrogen bonding. Compound 3a exhibits intermolecular hydrogen bonding, too. Furthermore, the computed Hirshfeld surface analysis confirms H-bonds and π–π stack interactions obtained by XRD packing analyses.
- Subjects
HYDROXYACETOPHENONES; MANNICH reaction; REGIOSELECTIVITY (Chemistry); NUCLEAR magnetic resonance spectroscopy; MORPHOLINE
- Publication
Molecules, 2019, Vol 24, Issue 3, p590
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules24030590