FEDERICO MARRONE

Dottore di ricerca

ciclo: XXXVI


supervisore: Prof Giancarlo Fabrizi

Titolo della tesi: SYNTHESIS OF POLYCYCLIC COMPOUNDS OF BIOLOGICAL INTEREST THROUGH TRANSITION METAL-CATALYZED AND METAL-FREE APPROACHES

Heterocycles and polycyclic molecular structures represent a privileged class of organic compounds because they are ubiquitous structural units in a broad variety of biologically and pharmacologically relevant natural products, medicinal molecules, and functional materials. In this context, the synthesis and functionalization of polycycles and heterocycles have become a steadily increasing driving force both in academia and industry. Transition-metal catalysis has traditionally been considered a strong pillar of catalysis and has mostly dominated the field of organic synthesis, establishing it as an essential tool in the synthesis of polycycles. Transition metals' feature to move between different oxidation states and form complexes with reagents in a catalytic cycle allows us to achieve unprecedented molecular transformations. Moreover, the reactivity and selectivity of these metal complexes can be fine-tuned according to the requirement of the catalytic process with the assistance of different factors, such as the steric and electronic nature of metal-coordinated ligands and counterions. In this way, these processes are in general highly efficient and hold tremendous potential for the development of new synthetic methodologies. The drawback of employing metals as catalysts is the purification of the synthesized compounds and in disposal of them from the reaction mixture. For this reason, another interesting tool that received a great deal of attention to easily obtain heterocyclic structure consists of the Diels-Alder reaction and dienes chemistry: over the past few years, this branch of modern chemistry has found applications in total synthesis as well as organic chemistry. Thus, the aim of this PhD thesis is to provide insight into different strategies and methodologies developed in the last three years for the synthesis of biologically interesting polycycles, with a focus on Pd, Au and Cu-catalyzed reactions and diene chemistry as powerful and versatile tools for the construction and functionalization of important heterocycles.

Produzione scientifica

11573/1716258 - 2024 - Palladium-Catalyzed Synthesis of 6-aryl Dopamine Derivatives
Calcaterra, Andrea; Fernández García, Santiago; Marrone, Federico; Bernini, Roberta; Fabrizi, Giancarlo; Goggiamani, Antonella; Iazzetti, Antonia - 01a Articolo in rivista
rivista: CATALYSTS (Basel: Molecular Diversity Preservation International) pp. - - issn: 2073-4344 - wos: (0) - scopus: (0)

11573/1688402 - 2023 - Synthesis of Functionalized 3H-pyrrolo-[1,2,3-de] Quinoxalines via Gold-Catalyzed Intramolecular Hydroamination of Alkynes
Iazzetti, Antonia; Fabrizi, Giancarlo; Goggiamani, Antonella; Marrone, Federico; Sferrazza, Alessio; Ullah, Karim - 01a Articolo in rivista
rivista: MOLECULES (Basel: MDPI Berlin: Springer, 1996-) pp. 1-12 - issn: 1420-3049 - wos: WOS:001046282200001 (1) - scopus: 2-s2.0-85167740224 (1)

11573/1664751 - 2022 - Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy
Arcadi, A.; Berden, G.; Ciogli, A.; Corinti, D.; Crestoni, M. E.; De Angelis, M.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Oomens, J.; Serraiocco, A. - 01a Articolo in rivista
rivista: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (Weinheim : Wiley-VCH-Verl.) pp. 1-10 - issn: 1099-0690 - wos: WOS:000884495100001 (2) - scopus: 2-s2.0-85142364350 (4)

11573/1620388 - 2022 - Synthesis of indole/benzofuran-containing diarylmethanes through palladium-catalyzed reaction of indolylmethyl or benzofuranylmethyl acetates with boronic acids
Arcadi, A.; Calcaterra, A.; Chiarini, M.; Fabrizi, G.; Fochetti, A.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Serraiocco, A. - 01a Articolo in rivista
rivista: SYNTHESIS (Stuttgart : Thieme Verlag) pp. 741-753 - issn: 0039-7881 - wos: WOS:000717220100001 (5) - scopus: 2-s2.0-85119479802 (5)

11573/1654400 - 2022 - One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids
Arcadi, Antonio; Calcaterra, Andrea; Fabrizi, Giancarlo; Fochetti, Andrea; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Mazzoccanti, Giulia; Serraiocco, Andrea - 01a Articolo in rivista
rivista: ORGANIC & BIOMOLECULAR CHEMISTRY (Royal Society of Chemistry:Thomas Graham House, Science Park, Cambridge CB4 0WF United Kingdom:011 44 1223 432360, EMAIL: sales@rsc.org, INTERNET: http://www.rsc.org, http://www.chensoc.org, Fax: 011 44 1223 423429) pp. 3160-3173 - issn: 1477-0520 - wos: WOS:000773645900001 (8) - scopus: 2-s2.0-85128383867 (8)

11573/1670190 - 2022 - Synthesis of Polysubstituted 1,2-Dihydro-3H-pyrrolo[1,2-a]indol-3-ones through Domino Palladium-Catalyzed Reactions of Indol-2-ylmethyl Acetates with 1,3-Dicarbonyl Derivatives
Iazzetti, A.; Arcadi, A.; Dessalvi, S.; Fabrizi, G.; Goggiamani, A.; Marrone, F.; Serraiocco, A.; Sferrazza, A.; Ullah, K. - 01a Articolo in rivista
rivista: CATALYSTS (Basel: Molecular Diversity Preservation International) pp. 1-18 - issn: 2073-4344 - wos: WOS:000902240000001 (4) - scopus: 2-s2.0-85144909600 (4)

11573/1620362 - 2021 - Synthesis of 4-substituted-1,2-dihydroquinolines by means of gold-catalyzed intramolecular hydroarylation reaction of n-ethoxycarbonyl-n-propargylanilines
Arcadi, A.; Calcaterra, A.; Fabrizi, G.; Fochetti, A.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Mazzoccanti, G.; Serraiocco, A. - 01a Articolo in rivista
rivista: MOLECULES (Basel: MDPI Berlin: Springer, 1996-) pp. 3366- - issn: 1420-3049 - wos: WOS:000660410600001 (5) - scopus: 2-s2.0-85108098751 (5)

11573/1620348 - 2021 - Synthesis of Polycyclic Chromene Cores through Gold (I)-Catalyzed Intramolecular Hydroarylation Reaction (IMHA)
Arcadi, A.; Fabrizi, G.; Fochetti, A.; Franzini, R.; Ghirga, F.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Serraiocco, A. - 01a Articolo in rivista
rivista: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (Wiley-VCH Verlag GmBH:PO Box 101161, D 69451 Weinheim Germany:011 49 6201 606147, EMAIL: service@wiley-vch.de, INTERNET: http://www.wiley-vch.de, Fax: 011 49 6201 606328) pp. 1676-1687 - issn: 1434-193X - wos: WOS:000631675400007 (5) - scopus: 2-s2.0-85102340191 (12)

11573/1492599 - 2020 - Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles
Arcadi, Antonio; Fabrizi, Giancarlo; Fochetti, Andrea; Ghirga, Francesca; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Mazzoccanti, Giulia; Serraiocco, Andrea - 01a Articolo in rivista
rivista: RSC ADVANCES (London: Royal Society of Chemistry) pp. 909-917 - issn: 2046-2069 - wos: WOS:000607364700033 (4) - scopus: 2-s2.0-85099340730 (5)

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