Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines
1,2- and 1,4-dihydropyridines and <i>N</i>-substituted 2-pyridones are very important structural motifs due to their synthetic versatility and vast presence in a variety of alkaloids and bioactive molecules. In this article, we gather and summarize the catalytic and stereoselective synth...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/17/6186 |
| _version_ | 1797582094819393536 |
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| author | Lucrezia Margherita Comparini Mauro Pineschi |
| author_facet | Lucrezia Margherita Comparini Mauro Pineschi |
| author_sort | Lucrezia Margherita Comparini |
| collection | DOAJ |
| description | 1,2- and 1,4-dihydropyridines and <i>N</i>-substituted 2-pyridones are very important structural motifs due to their synthetic versatility and vast presence in a variety of alkaloids and bioactive molecules. In this article, we gather and summarize the catalytic and stereoselective synthesis of partially hydrogenated pyridines and pyridones via the dearomative reactions of pyridine derivatives up to mid-2023. The material is fundamentally organized according to the type of reactivity (electrophilic/nucleophilic) of the pyridine nucleus. The material is further sub-divided taking into account the nucleophilic species when dealing with electrophilic pyridines and considering the reactivity manifold of pyridine derivatives behaving as nucleophiles at the nitrogen site. The latter more recent approach allows for an unconventional entry to chiral <i>N</i>-substituted 2- and 4-pyridones in non-racemic form. |
| first_indexed | 2024-03-10T23:17:00Z |
| format | Article |
| id | doaj.art-100e05caf63143dfa0b57b14803d812e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T23:17:00Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-100e05caf63143dfa0b57b14803d812e2023-11-19T08:32:30ZengMDPI AGMolecules1420-30492023-08-012817618610.3390/molecules28176186Recent Progresses in the Catalytic Stereoselective Dearomatization of PyridinesLucrezia Margherita Comparini0Mauro Pineschi1Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy1,2- and 1,4-dihydropyridines and <i>N</i>-substituted 2-pyridones are very important structural motifs due to their synthetic versatility and vast presence in a variety of alkaloids and bioactive molecules. In this article, we gather and summarize the catalytic and stereoselective synthesis of partially hydrogenated pyridines and pyridones via the dearomative reactions of pyridine derivatives up to mid-2023. The material is fundamentally organized according to the type of reactivity (electrophilic/nucleophilic) of the pyridine nucleus. The material is further sub-divided taking into account the nucleophilic species when dealing with electrophilic pyridines and considering the reactivity manifold of pyridine derivatives behaving as nucleophiles at the nitrogen site. The latter more recent approach allows for an unconventional entry to chiral <i>N</i>-substituted 2- and 4-pyridones in non-racemic form.https://www.mdpi.com/1420-3049/28/17/6186dearomatizationpyridinepyridinium saltasymmetric catalysisdihydropyridinetetrahydropyridine |
| spellingShingle | Lucrezia Margherita Comparini Mauro Pineschi Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines Molecules dearomatization pyridine pyridinium salt asymmetric catalysis dihydropyridine tetrahydropyridine |
| title | Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines |
| title_full | Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines |
| title_fullStr | Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines |
| title_full_unstemmed | Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines |
| title_short | Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines |
| title_sort | recent progresses in the catalytic stereoselective dearomatization of pyridines |
| topic | dearomatization pyridine pyridinium salt asymmetric catalysis dihydropyridine tetrahydropyridine |
| url | https://www.mdpi.com/1420-3049/28/17/6186 |
| work_keys_str_mv | AT lucreziamargheritacomparini recentprogressesinthecatalyticstereoselectivedearomatizationofpyridines AT mauropineschi recentprogressesinthecatalyticstereoselectivedearomatizationofpyridines |