Oxygen-containing molecules represent an indispensable class of heterocyclic compounds, due to their physicochemical properties. In particular, two of the most studied scaffolds are benzofurans and chromenes, widely present as pharmacophores in natural compounds (flavonoids, alkaloids, etc.) and synthetic drugs (antiarrhythmic, dermatological, and anticancer therapy). Due to their importance, chromene and benzofuran nucleus have gained enormous attention in the development of different synthetic strategies, involving a plethora of methods and type of reactions. In this context, Divergent Synthethic Strategy emerges as a promising tool, in order to obtain a variety of products under different reaction conditions, starting from similar simple and affordable substrates. Herein, we report our recent results in the development of a divergent regioselective synthesis of benzofuran and 4H-chromene nuclei. Specifically, we describe the reactivity of substituted o-propargylphenols under two different reaction conditions, both supported by microwave heating: using a catalytic amount of base we were able to selectively obtain substituted benzofuran, while in presence of a metal the reactivity shifted to the formation of chromenes. We also consider the limitations and the divergent mechanism of our approach.
o-Propargylphenols: A Gateway to Divergent Synthesis of 2-Substituted Benzofurans and Chromenes / A. Gritti, E. Brambilla, V. Pirovano, G. Abbiati. ((Intervento presentato al 28. convegno Elements of Future :Congresso Nazionale della Società Chimica Italiana : 26th - 30th August tenutosi a Milano nel 2024.
o-Propargylphenols: A Gateway to Divergent Synthesis of 2-Substituted Benzofurans and Chromenes
A. Gritti
Primo
;V. PirovanoPenultimo
;G. AbbiatiUltimo
2024
Abstract
Oxygen-containing molecules represent an indispensable class of heterocyclic compounds, due to their physicochemical properties. In particular, two of the most studied scaffolds are benzofurans and chromenes, widely present as pharmacophores in natural compounds (flavonoids, alkaloids, etc.) and synthetic drugs (antiarrhythmic, dermatological, and anticancer therapy). Due to their importance, chromene and benzofuran nucleus have gained enormous attention in the development of different synthetic strategies, involving a plethora of methods and type of reactions. In this context, Divergent Synthethic Strategy emerges as a promising tool, in order to obtain a variety of products under different reaction conditions, starting from similar simple and affordable substrates. Herein, we report our recent results in the development of a divergent regioselective synthesis of benzofuran and 4H-chromene nuclei. Specifically, we describe the reactivity of substituted o-propargylphenols under two different reaction conditions, both supported by microwave heating: using a catalytic amount of base we were able to selectively obtain substituted benzofuran, while in presence of a metal the reactivity shifted to the formation of chromenes. We also consider the limitations and the divergent mechanism of our approach.File | Dimensione | Formato | |
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