Nitroso Diels-Alder Cycloadducts Derived From N -Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity

• Published in: Molecules (Basel, Switzerland) Vol. 25; no. 3; p. 563
• Main Authors: Menichetti, Andrea, Berti, Francesco, Pineschi, Mauro
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 28.01.2020; MDPI
• Subjects: Bioactive compounds; Biological activity; Carbon; Chemistry; diversity oriented synthesis; functionalized piperidines; functionalized pyrroles; heterobicyclic compounds; Hydrogenation; nitroso diels-alder; Pharmaceutical sciences; Reagents; Review; Scaffolds; Titanium; heterobicyclic compounds; functionalized pyrroles; functionalized piperidines; diversity oriented synthesis; nitroso Diels-Alder
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules25030563

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 -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.