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Sintesi Organometallica (CHIM/06)

Research Group (with SSD): Organometallic chemistry research group (Chim 06).

Head of Laboratory: Prof. Giancarlo Fabrizi (Full Professor)

Website:

Main research topics: The research activities of the group are devoted to the development of innovative and sustainable transition metal catalyzed C-C and C-Heteroatom bond forming processes. Particularly, taking advantage of palladium, copper and gold catalysis, new efficient synthetic methods have been developed for the construction of a variety of polyfunctionalized molecules of biological interest (indoles, quinolones, carbazoles and benzodiazepine) identified and characterized using the main spettroscopic methods (NMR, IR and mass spectroscopy).

In this area, the main research topics are:

1.  Synthesis of novel heterocyclic compounds for antitumor activities

2.  Synthesis of 2-(aminomethyl)indoles

3.  Gold catalyzed assembly of heterocyclic rings

4.  Synthesis of nitrogen-containing polycylcic compounds

5.  Reactivity of propargylic derivatives in palladium catalyzed reactions

  1. Carbonylation reactions through in situ generation methodology of carbon monoxide
  2. Diazonium salts in palladium-catalyzed reactions
  3. C-H Bond Activation: C-C and C-N bond forming reactions
  4. Reactivity of b-enaminones in palladium and copper catalyzed reactions

5.  Chemoenzimatic reaction

6.   Green chemistry

National and International Collaborations:

The organometallic chemistry group collaborates with national and international research group to develop new research tools and provide consistent scientific data. These collaborations (listed below) often results in co-authored publication.

1.       Prof. Lucia Di Marcotullio – Dipartimento di chimica molecolare – Sapienza Università di Roma

2.       Prof. Antonio Arcadi – Dipartimento di scienze fisiche e chimiche- Università dell’Aquila

3.       Prof. Fabio Marinelli - Dipartimento di scienze fisiche e chimiche- Università dell’Aquila

4.       Prof. Marco Bandini – Dipartimento di chimica “Giacomo Ciamician” – Alma Mater Studiorum Università di Bologna

5.       Prof. Giovanni Poli - Institut Parisien de Chimie Moléculaire - Université Pierre et Marie Curie, Paris

Facilities: Bruker Avance 400 spectrometer, QP2010 Gas Chromatograph Mass spectrometer (EI ion source), Jasco FT/IR-430 spectrophotometer.

ERC panels:

PE4_10 - Heterogeneous catalysis
PE4_12 - Chemical reactions: mechanisms, dynamics, kinetics and catalytic reactions
PE5_13 - Homogeneous catalysis

PE5_17 - Organic chemistry


Grants (2015-2018):

2016 – Progetti di Ricerca di Ateneo MEDI, Università degli Studi di Roma “La Sapienza”.

Project: “Targeting hedgehog pathway: identification and sustainable synthesis of novel Smo and Gli inhibitors and their pharmacological effects in tumors and cancer stem cells”.

2016 – Progetti per avvio alla Ricerca, Università degli Studi di Roma “La Sapienza”,

Project: “Sintesi metallo assistita di derivati idolo[1,2-c]chinazolinonici”.

2015 – Progetti di Ricerca di Ateneo GRANDI, Università degli Studi di Roma “La Sapienza”.

Project: “Synthesis and evaluation of innovative molecular drugs in brain tumors treatment”.

2015 – Progetti per avvio alla Ricerca, Università degli Studi di Roma “La Sapienza”,

Project:“Impiego di b-enamminoni nella sintesi metallo-assistita di derivati eterociclici polifunzionalizzati”.


Laboratory Members:

1.       Prof. Antonella Goggiamani AP)

2.       Dr. Antonia Iazzetti


Publications (2015-2018):

1. Palladium-Catalyzed Cascade Approach to 12-(Aryl)Indolo [1,2-c]Quinazolin-6(5H)-ones. A. Arcadi, S. Cacchi, G. Fabrizi, F. Ghirga, A. Goggiamani, A. Iazzetti*, F. Marinelli Synthesis, 2018, 50, 1133.

2. Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61. A. Calcaterra, V. Iovine, B. Botta, D. Quaglio, I. D’Acquarica, A. Ciogli, A. Iazzetti, R. Alfonsi, L. Lospinoso Severini, P. Infante, L. Di Marcotullio, M. Mori, F. Ghirga, Journal Of Enzyme Inhibition And Medicinal Chemistry, 2017, 60 (4) 1469

3. 2-(Aminomethyl)-3-arylindoles from 3-(o-Trifluoroacetamidoaryl)-1-propargylic Alcohols, Aryl Halides, and Amines: A Domino Palladium-Catalyzed Three-Component Approach. S. Cacchi, G. Fabrizi, A. Goggiamani, A. Iazzetti, R. Verdiglione Synthesis, 2017, 49, 4163.

4. Design, Palladium-Catalyzed Synthesis, and Biological Investigation of 2-Substituted 3-Aroylquinolin-4(1H)-ones as Inhibitors of the Hedgehog Signaling Pathway. R. Alfonsi, B. Botta, S. Cacchi, , L. Di Marcotullio, G. Fabrizi, R. Faedda, A. Goggiamani, A. Iazzetti and M. Mori Journal of Medicinal Chemistry , 2017, 60 (4), 1469.

5. Construction of the 1,5-Benzodiazepine Skeleton from o-Phenylendiamine and Propargylic Alcohols via a Domino Gold-Catalyzed Hydroamination/Cyclization Process. S.Cacchi, G. Fabrizi, A. Goggiamani, A. Iazzetti, Organic Letters, 2016, 18 (15), 3511.

6. Total synthesis of (±)-Kuwanol e V. Iovine, I. Benni, R. Sabia, I. D’Acquarica, G. Fabrizi, B. Botta, A. Calcaterra Journal of Natural Products, 2016, 79, 2495.

7. A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles. S.Cacchi, G. Fabrizi, A. Goggiamani, A. Iazzetti, R. Verdiglione Tetrahedron, 2015,71, 9346.

8. A Palladium-Catalyzed Nucleophilic Substitution of Propargylic Carbonates and Meldrum's Acid Derivatives. I. Ambrogio, S. Cacchi, G. Fabrizi, A. Goggiamani, A. Iazzetti European Journal of Organic Chemistry, 2015, 3147.

9. Synthesis of Free NH 2-(Aminomethyl)indoles through Copper-Catalyzed Reaction of 3-(ortho-Trifluoroacetamidophenyl)-1-propargylic Alcohols with Amines and Palladium/Copper-Cocatalyzed Domino Three-Component Sonogashira Cross-Coupling/Cyclization/Substitution Reactions. S. Cacchi, G. Fabrizi, A. Iazzetti, C, Molinaro, R. Verdiglione, A. Goggiamani, Advanced synthesis & catalysis, 2015, 357, 1053.

10. Pd- and Rh-Catalyzed Hydroarylation of γ-(2-Methoxycarbonylphenyl)propargylic Alcohols: Approaches to 4- or 5-Substituted Seven-Membered Benzolactones and 3,3-Disubstituted Phthalides A. Arcadi, G. Fabrizi, A. Goggiamani, F. Marinelli, Journal of Organic Chemistry, 2015, 80, 6986.