Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis Article Swipe
Ghadah Aljohani
,
Musa A. Said
,
Dieter Lentz
,
Norazah Basar
,
Arwa Albar
,
Shaya Y. Al‐Raqa
,
Adeeb Al-Sheikh Ali
·
YOU?
·
· 2019
· Open Access
·
· DOI: https://doi.org/10.3390/molecules24030590
YOU?
·
· 2019
· Open Access
·
· DOI: https://doi.org/10.3390/molecules24030590
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.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3390/molecules24030590
- https://www.mdpi.com/1420-3049/24/3/590/pdf?version=1549533282
- OA Status
- gold
- Cited By
- 11
- References
- 40
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W2911490588
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Raw OpenAlex JSON
- OpenAlex ID
-
https://openalex.org/W2911490588Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.3390/molecules24030590Digital Object Identifier
- Title
-
Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-AnalysisWork title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2019Year of publication
- Publication date
-
2019-02-07Full publication date if available
- Authors
-
Ghadah Aljohani, Musa A. Said, Dieter Lentz, Norazah Basar, Arwa Albar, Shaya Y. Al‐Raqa, Adeeb Al-Sheikh AliList of authors in order
- Landing page
-
https://doi.org/10.3390/molecules24030590Publisher landing page
- PDF URL
-
https://www.mdpi.com/1420-3049/24/3/590/pdf?version=1549533282Direct link to full text PDF
- Open access
-
YesWhether a free full text is available
- OA status
-
goldOpen access status per OpenAlex
- OA URL
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https://www.mdpi.com/1420-3049/24/3/590/pdf?version=1549533282Direct OA link when available
- Concepts
-
Chemistry, Monoclinic crystal system, Intramolecular force, Hydrogen bond, Morpholine, Mannich reaction, Intermolecular force, Regioselectivity, Crystal structure, Carbon-13 NMR, Orthorhombic crystal system, Crystallography, Catalysis, Molecule, Stereochemistry, Organic chemistryTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
11Total citation count in OpenAlex
- Citations by year (recent)
-
2025: 2, 2023: 1, 2021: 1, 2020: 5, 2019: 2Per-year citation counts (last 5 years)
- References (count)
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40Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.methodologies, | 51 |
| abstract_inverted_index.regioselective | 22 |
| abstract_inverted_index.environmentally | 41 |
| abstract_inverted_index.crystallography. | 90 |
| abstract_inverted_index.microwave-assisted | 2 |
| abstract_inverted_index.well-characterized | 66 |
| abstract_inverted_index.4-hydroxyacetophenone | 12 |
| abstract_inverted_index.4-hydroxyacetophenone. | 62 |
| abstract_inverted_index.1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one | 79 |
| abstract_inverted_index.1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}ethan-1-one | 82 |
| cited_by_percentile_year.max | 98 |
| cited_by_percentile_year.min | 89 |
| corresponding_author_ids | https://openalex.org/A5074924436, https://openalex.org/A5086895412 |
| countries_distinct_count | 3 |
| institutions_distinct_count | 7 |
| corresponding_institution_ids | https://openalex.org/I23075662 |
| citation_normalized_percentile.value | 0.68119056 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | False |