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12 results on '"Marrone F"'

1. Synthesis of Functionalized 3H-pyrrolo-[1,2,3-de] Quinoxalines via Gold-Catalyzed Intramolecular Hydroamination of Alkynes

Author

Iazzetti, Antonia, Fabrizi, G., Goggiamani, Antonella, Marrone, Francesco, Sferrazza, A., Ullah, K., Iazzetti A. (ORCID:0000-0002-7792-774X), Goggiamani A., Marrone F., Iazzetti, Antonia, Fabrizi, G., Goggiamani, Antonella, Marrone, Francesco, Sferrazza, A., Ullah, K., Iazzetti A. (ORCID:0000-0002-7792-774X), Goggiamani A., and Marrone F.

Abstract

A gold-catalyzed protocol to obtain functionalized 3H-pyrrolo [1,2,3-de] quinoxalines from suitable substituted N-alkynyl indoles has been proposed. The mild reaction conditions were revealed to be compatible with different functional groups, including halogen, alkoxyl, cyano, ketone, and ester, allowing the isolation of title compounds with yields from good to high. A reaction mechanism has been proposed, and theoretical calculations have been provided to rationalize the final step of the hypothesized reaction mechanism. As quinoxaline-containing polycyclic compounds, this class of molecules may represent a valuable template in medicinal chemistry and material science.

Published
2023

2. Synthesis of 9,10-Dibenzoyl-phenanthrene Derivatives Through a Palladium-Catalyzed Domino Approach

Author

Arcadi, A., Fabrizi, G., Goggiamani, Antonella, Iazzetti, Antonia, Iavarone, Federica, Marrone, Francesco, Mazzoccanti, G., Sferrazza, A., Goggiamani A., Iazzetti A. (ORCID:0000-0002-7792-774X), Iavarone F. (ORCID:0000-0002-2074-5531), Marrone F., Arcadi, A., Fabrizi, G., Goggiamani, Antonella, Iazzetti, Antonia, Iavarone, Federica, Marrone, Francesco, Mazzoccanti, G., Sferrazza, A., Goggiamani A., Iazzetti A. (ORCID:0000-0002-7792-774X), Iavarone F. (ORCID:0000-0002-2074-5531), and Marrone F.

Abstract

A palladium-catalyzed domino approach toward synthetically challenging phenanthrene derivatives has been developed. The procedure involves a sequence of oxidative homocoupling, cyclization, and oxidation starting from deoxybenzoin derivatives halogenated in the ortho position. Good assembly efficiency and good functional group tolerance have been observed with yields from moderate to excellent. A plausible reaction mechanism has been proposed based on experimental results and literature data.image

Published
2023

3. Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy

Author

Arcadi, A., Berden, G., Ciogli, A., Corinti, D., Crestoni, M.E., Angelis, M. Hrabe de, Fabrizi, G., Goggiamani, A., Iazzetti, A., Marrone, F., Marsicano, V., Oomens, J., Serraiocco, A., Arcadi, A., Berden, G., Ciogli, A., Corinti, D., Crestoni, M.E., Angelis, M. Hrabe de, Fabrizi, G., Goggiamani, A., Iazzetti, A., Marrone, F., Marsicano, V., Oomens, J., and Serraiocco, A.

Abstract

Contains fulltext : 284404.pdf (Publisher’s version ) (Closed access)

Published
2022

4. Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy

Author

Arcadi, A., Berden, G., Ciogli, A., Corinti, D., Crestoni, M.E., Angelis, M. Hrabe de, Fabrizi, G., Goggiamani, A., Iazzetti, A., Marrone, F., Marsicano, V., Oomens, J., Serraiocco, A., Arcadi, A., Berden, G., Ciogli, A., Corinti, D., Crestoni, M.E., Angelis, M. Hrabe de, Fabrizi, G., Goggiamani, A., Iazzetti, A., Marrone, F., Marsicano, V., Oomens, J., and Serraiocco, A.

Abstract

Contains fulltext : 284404.pdf (Publisher’s version ) (Closed access)

Published
2022

5. 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

Author

Iazzetti, Antonia, Arcadi, A, Dessalvi, S, Fabrizi, G, Goggiamani, A, Marrone, F, Serraiocco, A, Sferrazza, A, Ullah, K, Iazzetti, A (ORCID:0000-0002-7792-774X), Iazzetti, Antonia, Arcadi, A, Dessalvi, S, Fabrizi, G, Goggiamani, A, Marrone, F, Serraiocco, A, Sferrazza, A, Ullah, K, and Iazzetti, A (ORCID:0000-0002-7792-774X)

Abstract

A straightforward assembly of polysubstituted 1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-ones through a domino palladium-catalyzed reaction of indol-2-ylmethyl acetates with 1,3-dicarbonyl derivatives is described. The key role of the features of the 1,3-dicarbonyls on the reaction outcome has been explored. The employment of 2-methylcyclohexan-1,3-dione as the dicarbonyl source could allow further challenging indole nucleus functionalizations.

Published
2022

6. Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy

Author

Arcadi, A, Berden, G, Ciogli, A, Corinti, D, Crestoni, Me, De Angelis, M, Fabrizi, G, Goggiamani, A, Iazzetti, Antonia, Marrone, F, Marsicano, V, Oomens, J, Serraiocco, A, Iazzetti, A (ORCID:0000-0002-7792-774X), Arcadi, A, Berden, G, Ciogli, A, Corinti, D, Crestoni, Me, De Angelis, M, Fabrizi, G, Goggiamani, A, Iazzetti, Antonia, Marrone, F, Marsicano, V, Oomens, J, Serraiocco, A, and Iazzetti, A (ORCID:0000-0002-7792-774X)

Abstract

The synthesis of (aminomethyl), (tosylmethyl), and (aryloxymethyl) indoles starting from indolylmethylacetates and N, O, and S soft nucleophiles has been developed. ESI-MS and IR multiple-photon dissociation (IRMPD) spectroscopy analyses confirm the reaction proceeds through a conjugate addition of the nucleophile to 2-alkylideneindolenines and 3-alkylideneindoleninium.

Published
2022

7. One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids

Author

Arcadi, A., Calcaterra, A., Fabrizi, G., Fochetti, A., Goggiamani, A., Iazzetti, Antonia, Marrone, F., Mazzoccanti, G., Serraiocco, A., Iazzetti A. (ORCID:0000-0002-7792-774X), Arcadi, A., Calcaterra, A., Fabrizi, G., Fochetti, A., Goggiamani, A., Iazzetti, Antonia, Marrone, F., Mazzoccanti, G., Serraiocco, A., and Iazzetti A. (ORCID:0000-0002-7792-774X)

Abstract

The functionalized 3,4-dihydroquinolin-2-one nucleus has been assembled in good to high yields through the sequential reaction of readily available N-Ts-o-aminobenzyl alcohols with 5-substituted Meldrum's acid derivatives under mild basic conditions. Highly diastereoselective synthesis of 3-substituted-4-phenyl-1-tosyl-3,4-dihydroquinolin-2(1H)-ones was accomplished from N-(2-(hydroxy(phenyl)methyl)phenyl)-4-methylbenzenesulfonamide under the same reaction conditions. Regarding the reaction mechanism, we hypothesized that the formation of dihydroquinolones proceeds through the in situ generation of aza-o-QMs followed by conjugate addition of enolate/cyclization/elimination of acetone and CO2

Published
2022

8. Synthesis of Polycyclic Chromene Cores through Gold (I)-Catalyzed Intramolecular Hydroarylation Reaction (IMHA)

Author

Arcadi, A., Fabrizi, G., Fochetti, A., Franzini, R., Ghirga, F., Goggiamani, A., Iazzetti, Antonia, Marrone, F., Serraiocco, A., Iazzetti A. (ORCID:0000-0002-7792-774X), Arcadi, A., Fabrizi, G., Fochetti, A., Franzini, R., Ghirga, F., Goggiamani, A., Iazzetti, Antonia, Marrone, F., Serraiocco, A., and Iazzetti A. (ORCID:0000-0002-7792-774X)

Abstract

A regioselective gold (I)-catalyzed approach for the construction of polycyclic chromene cores has been developed. The reaction proceeds in good to excellent yields under mild condition with a broad range of substrates providing a simple and efficient tool for the synthesis of pyranochromene derivatives. Moreover, the regiochemical control of the annulation of unsymmetrically substituted propargylic ethers has been investigated focusing on electronic/steric effects of the ligands of gold complexes as well as on the electronic effects of the groups on the aromatic rings.

Published
2021

9. Synthesis of 4-substituted-1,2-dihydroquinolines by means of gold-catalyzed intramolecular hydroarylation reaction of n-ethoxycarbonyl-n-propargylanilines

Author

Arcadi, A., Calcaterra, A., Fabrizi, G., Fochetti, A., Goggiamani, A., Iazzetti, Antonia, Marrone, F., Marsicano, V., Mazzoccanti, G., Serraiocco, A., Iazzetti A. (ORCID:0000-0002-7792-774X), Arcadi, A., Calcaterra, A., Fabrizi, G., Fochetti, A., Goggiamani, A., Iazzetti, Antonia, Marrone, F., Marsicano, V., Mazzoccanti, G., Serraiocco, A., and Iazzetti A. (ORCID:0000-0002-7792-774X)

Abstract

An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-Npropargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-metasubstituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.

Published
2021

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