Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis.

Molecules 2019 Feb 7;24(3). Epub 2019 Feb 7.

Chemistry Department, College of Science, Taibah University, P.O. Box 30002, Al-Madinah Al-Munawarah 14177, Saudi Arabia.

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, C NMR, and mass spectrometry. The structures of 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one () and 1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}ethan-1-one () were determined by single crystal X-ray crystallography. Compound and crystallize in monoclinic, 2₁/, and orthorhombic, , respectively. The most characteristic features of the molecular structure of is that the morpholine fragment adopts a chair conformation with strong intramolecular hydrogen bonding. Compound exhibits intermolecular hydrogen bonding, too. Furthermore, the computed Hirshfeld surface analysis confirms H-bonds and π⁻π stack interactions obtained by XRD packing analyses.

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http://dx.doi.org/10.3390/molecules24030590DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6384783PMC
February 2019

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