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Molecules 2019, 24(3), 590; https://doi.org/10.3390/molecules24030590

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

1
Chemistry Department, College of Science, Taibah University, P.O. Box 30002, Al-Madinah Al-Munawarah 14177, Saudi Arabia
2
Institut für Chemie und Biochemie, Anorganische Chemie, Freie Universität Berlin, Fabeckstr. 34-36, 14195 Berlin, Germany
3
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Malaysia
4
Department of Physics, College of Science, Jeddah University, P.O. BOX 80327, Jeddah 21589, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Academic Editor: John Spencer
Received: 23 December 2018 / Revised: 31 January 2019 / Accepted: 2 February 2019 / Published: 7 February 2019
(This article belongs to the Special Issue Microwave-mediated Chemistry)
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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. View Full-Text
Keywords: Mannich bases; 4-hydroxyacetophenone; microwave irradiation; regioselectivity; X-ray; HSA Mannich bases; 4-hydroxyacetophenone; microwave irradiation; regioselectivity; X-ray; HSA
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Aljohani, G.; Said, M.A.; Lentz, D.; Basar, N.; Albar, A.; Alraqa, S.Y.; Ali, A. .-S. Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis. Molecules 2019, 24, 590.

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