Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity
This review focuses upon the use of nitroso Diels−Alder reactions as a structural complexity generating reaction that has been so far a quite scarcely treated topic, despite its potential. In particular, the use of <i>N</i>-acyl-1,2-dihydropyridines as a non-symmetrical diene c...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/3/563 |
| _version_ | 1819001102440333312 |
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| author | Andrea Menichetti Francesco Berti Mauro Pineschi |
| author_facet | Andrea Menichetti Francesco Berti Mauro Pineschi |
| author_sort | Andrea Menichetti |
| collection | DOAJ |
| description | This review focuses upon the use of nitroso Diels−Alder reactions as a structural complexity generating reaction that has been so far a quite scarcely treated topic, despite its potential. In particular, the use of <i>N</i>-acyl-1,2-dihydropyridines as a non-symmetrical diene component in nitroso Diels−Alder reactions encompasses an initial diversification of pathways giving rise to different cycloadducts (direct and inverse). Selective elaborations of these cycloadducts, basically using a reagent-based approach, deliver a discrete number of structurally diverse compounds, including some original heterobicyclic scaffolds and functionalized heterocycles. This forward synthetic planning allowed the individuation of a new biologically active compound based on a novel oxadiaza-bicyclic-[3.3.1]-nonene scaffold which is still under preclinical evaluation. |
| first_indexed | 2024-12-20T22:43:52Z |
| format | Article |
| id | doaj.art-f42c7838de4341e0a9e1624093f0530e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-20T22:43:52Z |
| publishDate | 2020-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f42c7838de4341e0a9e1624093f0530e2022-12-21T19:24:25ZengMDPI AGMolecules1420-30492020-01-0125356310.3390/molecules25030563molecules25030563Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular DiversityAndrea Menichetti0Francesco Berti1Mauro Pineschi2Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyThis review focuses upon the use of nitroso Diels−Alder reactions as a structural complexity generating reaction that has been so far a quite scarcely treated topic, despite its potential. In particular, the use of <i>N</i>-acyl-1,2-dihydropyridines as a non-symmetrical diene component in nitroso Diels−Alder reactions encompasses an initial diversification of pathways giving rise to different cycloadducts (direct and inverse). Selective elaborations of these cycloadducts, basically using a reagent-based approach, deliver a discrete number of structurally diverse compounds, including some original heterobicyclic scaffolds and functionalized heterocycles. This forward synthetic planning allowed the individuation of a new biologically active compound based on a novel oxadiaza-bicyclic-[3.3.1]-nonene scaffold which is still under preclinical evaluation.https://www.mdpi.com/1420-3049/25/3/563diversity oriented synthesisnitroso diels-alderheterobicyclic compoundsfunctionalized piperidinesfunctionalized pyrroles |
| spellingShingle | Andrea Menichetti Francesco Berti Mauro Pineschi Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity Molecules diversity oriented synthesis nitroso diels-alder heterobicyclic compounds functionalized piperidines functionalized pyrroles |
| title | Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
| title_full | Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
| title_fullStr | Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
| title_full_unstemmed | Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
| title_short | Nitroso Diels-Alder Cycloadducts Derived From <i>N</i>-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
| title_sort | nitroso diels alder cycloadducts derived from i n i acyl 1 2 dihydropyridines as a new platform to molecular diversity |
| topic | diversity oriented synthesis nitroso diels-alder heterobicyclic compounds functionalized piperidines functionalized pyrroles |
| url | https://www.mdpi.com/1420-3049/25/3/563 |
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