Contacts:
www.linkedin.com/in/elisabetta-rosadoni
Supervisor(s):
Prof. Fabio Bellina
Title of the PhD project:
C-H bonds activation of N-containing heterocycles
Abstract of the PhD project:
The development in recent decades of procedures for the direct functionalization of non-activated C-H bonds has created the possibility for medicinal chemistry to be able to increasingly use a synthetic strategy known as late-stage functionalization (LSF). In accordance with this strategy, C-H bonds are seen as functional groups and, therefore, as potential diversification points to generate new analogues from existing pharmaceutical leads, without having to resort to de novo synthetic procedures. As known, the main problem of the functionalization procedures of C-H bonds, in addition to the difficulties of reactivity related to the strength of these bonds, is represented by regioselectivity. In the context of LSF reactions, procedures involving C-H bonds of heterocycles have particular interest. In these cases, in fact, the presence of one or more heteroatoms grants a more marked differentiation of the different C-H bonds present, thus allowing an easier development of regioselective procedures.
Therefore, the propose of this PhD project will be aimed at identifying synthetic procedures for the selective functionalizing of N-containing heterocyclic systems, given their considerable importance as key structures in many biologically active compounds as well as in materials science, with particular attention to the development of procedure for the C(sp3)-H bonds functionalization.
Publications:
• Bellina, F.; Biagetti, M.; Guariento, S.; Lessi, M.; Fausti, M.; Ronchi, P.; Rosadoni, E., Ligand-free Pd/Ag-mediated dehydrogenative alkynylation of imidazole derivatives. RSC Advances 2021, 11 (41), 25504.
• Bellina, F.; La Manna, M.; Rosadoni, E., Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes. Current Organic Chemistry 2021, 25 (18), 2116-2141.
• Rosadoni, E.; Banchini, F.; Bellini, S.; Lessi, M.; Pasquinelli, L.; Bellina, F., Ligandless Palladium-Catalyzed Direct C-5 Arylation of Azoles Promoted by Benzoic Acid in Anisole. Molecules 2022, 27 (23), 8454.
• Rosadoni, E.; Bellina, F.; Lessi, M.; Micheletti, C.; Ventura, F.; Pucci, A., Y-shaped alkynylimidazoles as effective push-pull fluorescent dyes for luminescent solar concentrators (LSCs). Dyes and Pigments 2022, 201, 110262.
• Rosadoni, E.; Bombonato, E.; Del Vecchio, A.; Guariento, S.; Ronchi, P.; Bellina, F., Direct Decarboxylative C-2 Alkylation of Azoles through Minisci-Type Coupling. The Journal of Organic Chemistry 2023, 88 (19), 14236.
• Malpicci, D.; Maver, D.; Rosadoni, E.; Colombo, A.; Lucenti, E.; Marinotto, D.; Botta, C.; Bellina, F.; Cariati, E.; Forni, A., 3-ethynyltriimidazo[1,2-a:1',2'-c:1'',2''-e][1,3,5]triazine dual short- and long-lived emissions with crystallization-enhanced feature: role of hydrogen bonds and π-π interactions. Molecules 2024, 29(9), 1967.
• Rosadoni, E.; Ballerini, L.; Del Vecchio, A.; Bellina, F., Synthesis of 3-Aryl Substituted Triimidazotriazines via Regioselective Direct Arylation. Asian Journal of Organic Chemistry 2024, e202400082.
• Del Vecchio, A.; Rosadoni, E.; Ballerini, L; Cuzzola, A.; Lipparini, F.; Ronchi, P.; Guariento, S.; Biagetti, M.; Lessi, M.; Bellina, F., Selective Direct C-H Arylation of imidazo[2,1-b]thiazole. ChemistryOpen 2024, e202400180
Oral communications at conferences:
• Rosadoni, E.; Del Vecchio, A.; Cuzzola, A.; Ballerini, L; Lipparini, F.; Ronchi, P.; M.; Lessi, M.; Bellina, F. “Selective C-H Arylation of Non-Substituted Imidazo[2,1-b]thiazole: Towards a Modular Approach for Biologically Active Compounds”, CIRCC – PhD Day 2024, 18 April 2024, Pisa (Italy).
• Rosadoni, E.; Del Vecchio, A.; Ronchi, P.; Bellina, F. “Direct C-2 alkylation of imidazoles through Minisci-type reaction”, ISOS 2024, 16 – 20 June 2024, Gargnano (Italy).
• Rosadoni, E.; “Direct C-H functionalization of azoles through radical reactions”, CFF 2024 - Chemistry for the Future, International Conference, 3 – 5 July 2024, Pisa (Italy).
• Rosadoni, E.; Del Vecchio, A.; Ronchi, P.; Bellina, F. “Direct C-H functionalization of azoles through radical reactions”, 29th Congress of the International Society of Heterocyclic Chemistry, 21 – 26 July 2024, Aveiro, Portugal.
• Bellina, F; Lessi, M.; Ronchi, P.; Guariento, S.; Biagetti, M.; Fausti, M.; Rosadoni, E., “Ligand-free dehydrogenative alkynylation of imidazoles”, ESOC 2021, European Symposium on Organic Chemistry, 5 – 6, July 2021, online.
• Bellina, F; Biagetti, M.; Fausti, M.; Granucci, G.; Guariento, S.; Lessi, M.; Micheletti, C.; Pucci, A.; Ronchi, P.; Rosadoni, E., “Pd/Ag-mediated dehydrogenative alkynylation of imidazoles”, SCI 2021, XXVII National Congress of the Italian Chemical Society, 14 – 23 September 2021, online.
• Rosadoni, E.; Lessi, M.; Ronchi, P.; Bellina, F., “Direct C-2 alkylation of azoles by decarboxylative coupling”, CINMPIS Days Pisa 2023; 9 – 11 February 2023, Pisa (Italy).
• Rosadoni, E.; Lessi, M.; Ronchi, P.; Bellina, F., “Direct C-2 alkylation of imidazoles derivatives through decarboxylative coupling”, CDCO 2023, XLI National Congress of the organic chemistry division of the Italian Chemical Society, 10 – 14 September 2023, Rome (Italy).
Poster communications at conferences:
1. Rosadoni, E.; Biagetti, M.; Fausti, M.; Granucci, G.; Guariento, S.; Lessi, M.; Micheletti, C.; Pucci, A.; Ronchi, P.; Bellina, F., “C-2 dehydrogenative alkynylation of imidazoles”, CFF 2021 - Chemistry for the Future, International Conference, 30 June – 2 July 2021, online. Poster and flash presentation.
2. Rosadoni, E.; Pucci, A.; Lessi, M.; Ventura, F.; Micheletti, C.; Bellina, F., “New push-pull alkynylimidazoles as fluorescent dyes for Luminescent Solar Concentrators (LSCs)”, 22nd Tetrahedron Symposium, International Conference, 28 June – 1 July 2022, Lisbon (Portugal).
3. Rosadoni, E.; Lessi, M.; Ronchi, P.; Bellina, F., “Direct C-2 alkylation of imidazole derivatives through decarboxylative coupling”, CFF 2023 - Chemistry for the Future, International Conference, 28 – 30 June 2023, Pisa (Italy).
Other achievements:
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