Cargando…
Nitroso Diels-Alder Cycloadducts Derived From N-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 N-acyl-1,2-dihydropyridines as a non-symmetrical diene component in nitroso Diels–Ald...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7038088/ https://www.ncbi.nlm.nih.gov/pubmed/32012951 http://dx.doi.org/10.3390/molecules25030563 |
_version_ | 1783500573690036224 |
---|---|
author | Menichetti, Andrea Berti, Francesco Pineschi, Mauro |
author_facet | Menichetti, Andrea Berti, Francesco Pineschi, Mauro |
author_sort | Menichetti, Andrea |
collection | PubMed |
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 N-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. |
format | Online Article Text |
id | pubmed-7038088 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-70380882020-03-10 Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity Menichetti, Andrea Berti, Francesco Pineschi, Mauro Molecules Review 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 N-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. MDPI 2020-01-28 /pmc/articles/PMC7038088/ /pubmed/32012951 http://dx.doi.org/10.3390/molecules25030563 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Review Menichetti, Andrea Berti, Francesco Pineschi, Mauro Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
title | Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
title_full | Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
title_fullStr | Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
title_full_unstemmed | Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
title_short | Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity |
title_sort | nitroso diels-alder cycloadducts derived from n-acyl-1,2-dihydropyridines as a new platform to molecular diversity |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7038088/ https://www.ncbi.nlm.nih.gov/pubmed/32012951 http://dx.doi.org/10.3390/molecules25030563 |
work_keys_str_mv | AT menichettiandrea nitrosodielsaldercycloadductsderivedfromnacyl12dihydropyridinesasanewplatformtomoleculardiversity AT bertifrancesco nitrosodielsaldercycloadductsderivedfromnacyl12dihydropyridinesasanewplatformtomoleculardiversity AT pineschimauro nitrosodielsaldercycloadductsderivedfromnacyl12dihydropyridinesasanewplatformtomoleculardiversity |