Ritratto di antonia.iazzetti@uniroma1.it


Corso di Chimica Organica - canale 1 [Corso di Laurea in Scienze Naturali, Facoltà di Scienze Matematiche, Fisiche e Naturali]


Le lezioni di Chimica Organica avranno inizio lunedì 28 settembre;saranno erogate in presenza e potranno essere fruite anche a distanza secondo le modalità indicate da  Sapienza

Per maggiori dettagli consultare i  seguenti link






Per gli studenti prenotati, le lezioni in presenza si svolgeranno in aula 8 di Geochimica [CU009-E01PR1L002] secondo il seguente orario

Lunedì 9:00-11:00   

Mercoledì 11:00 - 14:00


Per seguire le lezioni a distanza occorrerà collegarsi tramite la piattaforma zoom ai link seguenti


Lunedì 9:00-11:00: https://zoom.us/j/98593373376?pwd=Q0R3c2xMc1ZlU2JaalpPWXNJTG0xZz09

ID riunione: 985 9337 3376 Passcode: dZr3n0


Mercoledì 11:00 -14:00: https://zoom.us/j/94969796436?pwd=dkorS2VpYkpEWU5hS0g5SUozSjIrZz09

ID riunione: 949 6979 6436 Passcode: eSQ6m2




Venerdì 11-13
Nuovo edificio di Chimica (CU032), piano III, laboratorio 1

Current Position
Research Fellow (RTDA) Dept. Chimica e Tecnologie del Farmaco Sapienza University of Rome.
2013: PhD in Pharmaceutical Sciences.
Dissertation title: Transition Metal Catalysis in C-C and C- Heteroatom Bonds Forming Reactions ; Sapienza , University of Rome.
2010: Pharmacist licensure; Sapienza , University of Rome.
2009: Master s degree in Pharmaceutical Chemistry and Technologies.
Dissertation title: Sintesi di 1-aril-3- amminopropan-2-oni attraverso la reazione palladio catalizzata dei composti propargilici con le ammine ; Sapienza , University of Rome.
Academic Appointments
2013-2018: Funded researcher, Dept. Chimica e Tecnologie del Farmaco Sapienza University of Rome.
Teaching Experience
Teacher in charge for the course of Organic Chemistry; Faculty of Mathematics, Phisys and Natural Sciences; Sapienza , University of Rome.
2017-2020: Member of examination board for:
Organic Chemistry I; Master s degree in chemistry and Pharmaceutical Technology; Faculty of Pharmacy and Medicine; Sapienza , University of Rome.
Organic Chemistry II; Master s degree in chemistry and Pharmaceutical Technology; Faculty of Pharmacy and Medicine; Sapienza , University of Rome.
Advanced Synthesis in Organic Chemistry; Master s degree in chemistry and Pharmaceutical Technology; Faculty of Pharmacy and Medicine; Sapienza , University of Rome.

Supplementary teaching course for Organic Chemistry I; Master s degree in chemistry and Pharmaceutical Technology; Faculty of Pharmacy and Medicine; Sapienza , University of Rome.
Teaching support activities for Organic Chemistry I, Organic Chemistry II, and Advanced Synthesis in Organic Chemistry; Master s degree in chemistry and Pharmaceutical Technology; Faculty of Pharmacy and Medicine; Sapienza , University of Rome.

Funding Information as Investigator:
2018: Horizon 2020
Project: Separation, fractionation and isolation of biologically active natural substances from corn oil and other side streams - ExCornsEED
2017: Programmi di Riecerca Scientifica di Rilevante Interesse Nazionale, PRIN 2017. Project: Targeting Hedgehog pathway: Virtual screening identification and sustainable synthesis of novel Smo and Gli inhibitors and their pharmacological drug delivery strategies for improved therapeutic effects in tumors
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 .
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 .
2013: Progetti di Ricerca di Ateneo MEDI, Università degli Studi di Roma La Sapienza . Project: Sintesi in fase omogenea ed eterogenea di derivati eterociclici azotati ed ossigenati mediante attivazione metallo-assistita del legame Carilico-H e studio meccanicistico di alcuni passaggi reattivi connessi alla procedura .
2012: Programmi di Riecerca Scientifica di Rilevante Interesse Nazionale, PRIN 2012. Project: Identificazione, sintesi sostenibile e studio dell efficacia di nuovi farmaci molecolari nei tumori del sistema nervoso .
Funding Information as Principal Investigator:
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 per avvio alla Ricerca, Università degli Studi di Roma La Sapienza , Project: Impiego di beta-enamminoni nella sintesi metallo-assistita di derivati eterociclici polifunzionalizzati .

Research Activities
As supported by scientific papers, research activities have been focused on transition metal-catalyzed organic synthesis. 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, such as indoles, quinolones, carbazoles and benzodiazepine. These studies allowed the creation of several libraries of compounds that have been identified and characterized using the main spectroscopic techniques (Nuclear Magnetic Resonance - NMR, Infrared Spacroscopy - FT-IR, and Mass Spectrometry- MS). Particularly, developed topics are:
1. Gold catalyzed assembly of heterocyclic rings
The studies carried out in this field have been allowed the development of the following synthetic approaches:
Synthesis of pyrano[2,3-f]chromen-2-ones and of pyrano[3,2-g]chromen-2-ones
Regioselective access to 10-substituted-2H,8H-pyrano[2,3-f]chromen-2-ones through the gold-catalyzed intramolecular hydroarylation reaction of 7-(prop-2-yn-1-yloxy)-2H-chromen-2-one derivatives at their C-8 position was investigated by tuning the electronic and steric properties of the ligand on the gold complex employed. On the other hand, the combination of the gold-catalyzed intramolecular hydroarylation of 8-iodo-7-(prop-2-yn-1-yloxy)-2H-chromen-2-one derivatives followed by selective palladium/formate C I reduction allows for the exclusive formation of 2H,8Hpyrano[3,2-g]chromen-2-one regioisomers. The development of these two protocols provides versatile synthetic tools required for exploring the biological activities of these new pyranocoumarin derivatives.
Synthesis of 1,5-Benzodiazepine derivatives
A new method for the preparation of 1,5 benzodiazepine bearing different substituent on the 2 and 4 position has been delveloped. Reaction proceeds through a domino hydroamination/cyclization process involving the use of o-phenylendiamine and propargilic alcohols.
Stereo- and regioselective synthesis of Z-enamines
Enamines are a class of valuable synthetic intermediates used for the preparation of different heterocyclic compounds. For this reason, it appeared of interest to study a new approach to their synthesis. This study allowed the development of a new and versatile method for the stereo- and regioselective conversion of 2-(arylethynyl) pyridines into the corresponding enamines in the presence of a gold catalyst and anilines. The reaction, which proceeds with moderate-to-excellent yields, significantly extends the scope of the hydroamination of unsymmetrical internal alkynes and tolerates a range of functional groups on alkynes.

2. Synthesis of nitrogen-containing polycylcic compounds
Palladium catalysis has been applied to develop new and selective approaches to the construction of a wide variety of functionalized indole-fused compound such as:
a) Dibenzo[a,c]carbazoles from 2-(2-bromoaryl)-3-arylindoles
This synthesis is based on an aminopalladation/reductive elimination reaction followed by an intermolecular C-H functionalizzation/C-C bond formation step. The process provides a new and versatile approach for the construction of the dibenzo [a, c] carbazole ring.
b) 12-(aryl) indolo [1,2 c]quinazolin-6(5H)-ones
The quinazolinone nucleus is a key constituent of many natural products. Due to their importance a great deal of attention has been devoted to developing new synthetic approach to this class of compounds. Particularly two main methodology have been described:
A palladium-catalyzed cascade approach in which, starting from the o-(o-aminophenylethyny)) trifluoroacetanilides, the aminoarylation of the triple bond with aryl iodides, aryl bromides and arendiazonium salts is followed by the cyclization of the resulting 3-arylindole.
The methodology is quite versatile and tolerates a variety of useful functional groups.
A palladium-catalyzed direct arylation process in which the 12-(aryl) indolo [1,2 c]quinazolin-6(5H)-ones are obtained through the direct arylation of N-benzyl and NH-free indolo [1,2 c]quinazolin-6(5H)-ones with aryl halides.
c) Indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives
An efficient procedure for the preparation of 12-arylindolo[1,2-c]quinazolines from o-(o-aminophenylethynyl) trifluoroacetanilides and arylboronic acids, by avoiding the isolation of intermediate indoles has been reported. Starting from indoles, or from o-(o-aminophenylethynyl)aniline, selective formation of 12-unsubstituted[1,2-c]quinazolines was accomplished, without competitive formation of products derived from C-3 functionalization at the indole moiety.
3. Synthesis of novel heterocyclic compunds for antitumor activities
2-Substituted 3-aroylquinolin-4(1H)-ones, prepared through a palladium-catalyzed carbonylative cyclization of N-(2-iodoaryl)enaminones, proved to inhibit efficiently the Hedgehog pathway through direct antagonism of the wild-type and drug-resistant form of the Smoothened receptor. Notably, these compounds repressed the Hh-dependent growth events and the proliferation of tumor cells with aberrant activation of the Hh pathway, which plays a crucial role in development and tumorigenesis.
4. Synthesis of 2-(aminomethyl )indoles
Because of the importance of this class of compounds we decided to investigate for the construction of the 2- (aminomethyl)indole nucleus through different approaches:
a) Synthesis of 2-(aminomethyl)indoles through Cu-catalyzed reaction
Free NH 2-(aminomethyl)indoles have been prepared via copper-catalyzed cyclization of 3-(ortho- trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficient domino three-component Sonogashira cross- coupling/cyclization/substitution process that, omitting the isolation of 3- (ortho-trifluoroacetamidophenyl)- 1-propargylic alcohols, provides access to this class of compounds by treating 2 iodotrifluoroacetanilides, propargylic alcohols, and primary or secondary amines with a copper/palladium catalyst system.
b) Synthesis of 2-(aminomethyl)indoles through a domino Pd-catalyzed three component approach
2-(Aminomethyl)-3-arylindoles have been synthesized through a domino Pd-catalyzed three-component approach from 3-(o-Trifluoroacetamido- ary1)-1-propargylic alcohols, aryl halides, and amines.

5. Copper catalyzed C-H Functionalization Processes
To this regard, we have developed a straightforward approach to the construction of the multisubstituted imidazo[1,2-a]pyridine skeleton from N-(2-pyridinyl)enaminones trough a copper catalyzed C-N bond forming reaction. The process may represent a useful alternative to known procedures that allow the synthesis of this heterocyclic nucleus present in a wide variety of biologically active natural compounds and commercially available synthetic drugs.
6. Reactivity of propargylic derivatives in palladium catalyzed reactions
Propargylic esters are versatile compounds that are known to undergo several synthetically useful Pd- catalyzed transformations. These studies have been focused on the reaction of propargylic carbonates with:
a) Meldrum s acid derivative that gives the SN2-like substitution product.
b) Secondary amines that provides access to 2-amino ketones.
7. Assembly and functionalization of indole nucleus through palladium-catalyzed processes
The indole nucleus is a key structural feature present in several biologically active natural compounds and in a wide range of pharmaceuticals. Because of this a great deal of effort has been devoted to its construction and functionalization by means of Pd-catalyzed processes.
8. Other topics
a) Synthesis of functionalized 2,3-dihydrofurans:an efficient palladium-catalyzed oxyarylation approach to 2,3-dihydrofurans from of allyl- -ketoesters has been developed b) Copper-catalyzed oxidation reactions: a novel copper-catalyzed approach to benzils from readily available deoxybenzoins under neutral conditions using air as oxidant has been developed. c) Pd-catalyzed aromatic sulfonilation: allylic sulfones are proved to be precursor of aryl sulfones via a domino sequence involving in situ generation of sulfinate anions and subsequent cross-coupling with aryl iodides or bromides d) Insights into the chemical stability of GANT61: the mechanism and the kinetic of hydrolysis of GANT61 (inhibitor of hedgehog signaling pathway) have been studied combining NMR spectroscopy, analytical studies, molecular modeling and functional assay in cells.
Keywords: Organic synthesis, Organometallic chemistry, Homogeneous catalysis, Heterocycles

Scientific Publications on International Journals
1. The Pictet-Spengler Reaction Updates Its Habits. A.Calcaterra, L.Mangiardi, G. Delle Monache, D. Qauglio, S. Balducci, S. Berardozzi, A. Iazzetti, R. Franzini, B. Botta and F. Ghirga. Molecules, 2020, 25, 414 [IF: 3.06; Citations:0]
2. Synthesis of pyrano[2,3-f] chromen-2-ones vs. pyrano[3,2-g] chromen-2-ones through site controlled gold-catalyzed annulations. A. Arcadi, A. Ciogli, G. Fabrizi, A. Fochetti, R. Franzini, F. Ghirga, A. Goggiamani, A. Iazzetti* Org. Biomol. Chem., 2019, 17, 10065. [IF: 3.49; Citations:0]
3. Palladium-Catalyzed C12-Selective Direct Arylation of [1,2-c]Quinazolin-6(5H)-ones. A. Arcadi, S. Cacchi, G. Fabrizi, A. Fochetti, F. Ghirga, A. Goggiamani*, A. Iazzetti*, F. Marinelli. Synthesis 2019. [IF: 2.867; Citations:0]
4. Stereo- and regioselective gold(I)-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines. S. Cacchi, G. Fabrizi, A. Fochetti, F. Ghirga, A. Goggiamani, A. Iazzetti*. Org. Biomol. Chem., 2019, 17, 527. [IF: 3.49; Citations:2]

5. Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal. A. Arcadi, S. Cacchi, G. Fabrizi, F. Ghirga, A. Goggiamani, A. Iazzetti*, F. Marinelli*. Beilstein J. Org. Chem., 2018,14, 2411. [IF: 2.595; Citations:5]
6. 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(05) 1133. [IF: 2.867; Citations:5]
7. Copper-Catalyzed C-N Bond Formation via C-H Functionalization: Facile Synthesis of Multisubstituted Imidazo[1,2- a ]pyridines from N -(2-Pyridinyl)enaminones S. Cacchi, A. Ciogli, N. Demitri, G. Fabrizi, F. Ghirga, A. Goggiamani, A. Iazzetti*, D. Lamba. Synthesis,2018, 50(17), 3513. [IF: 2.867; Citations:5]
8. 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, 2018, 33(1), 349. [IF: 4.027; Citations:12]
9. 2-(Aminomethyl)-3-arylindoles from 3-(o-Trifluoroacetamidoaryl1)-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. [IF: 2.722; Citations:4]
10. 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. [IF: 6.253; Citations:16]
11. 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. lazzetti, Organic Letters, 2016, 18 (15), 3511. [IF: 6.579; Citations:17]
12. A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles. S.Cacchi, G. Fabrizi, A. Goggiamani, A. lazzetti, R. Verdiglione Tetrahedron, 2015, 71, 9346. [IF: 2.645; Citations:13]
13. 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. [IF: 3.068; Citations: 5]
14. 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. [IF: 6.453; Citations:15]
15. Copper-Catalyzed Oxidation of Deoxybenzoins to Benzils under Aerobic Conditions. S.Cacchi, G. Fabrizi, A, Goggiamani, A. lazzetti, R. Verdiglione. Synthesis, 2013, 45, 1701. [IF: 2.443; Citations:13]
16. 2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2- alkynyItrifluoroacetanilides with arylboronic acids under oxidative conditions. A.Arcadi, S. Cacchi, G. Fabrizi, A. Goggiamani, A. Iazzetti and F. Marinelli Organic. & Biomolecular Chemistry., 2013, 11, 545. [IF: 3.847; Citations:29]
17. Dibenzo[a,c]carbazoles from 2-(2-bromoaryl)-3-arylindoles via a palladiumcatalyzed intramolecular C-H functionalization'C-C bond formation process. S. Cacchi, G. Fabrizi, A. Goggiamani and A. lazzetti. Organic. & Biomolecular Chemistry, 2012, 10, 9142. [IF: 3.568; Citations:17]
18. Palladium-catalyzed synthesis of 2-amino ketones from propargylic carbonates and secondary amines. S.Cacchi, G. Fabrizi, E. Filisti, A. Goggiamani, A. Iazzetti and L. Maurone. Organic & Biomolecular Chemistry, 2012, 10, 4699. [IF: 3.568; Citations:8]
19. Functionalized 2,3-dihydrofurans via palladium-catalyzed oxyarylation of a-allyl-B-ketoesters S.Cacchi, G. Fabrizi, A. Goggiamani, A. Iazzetti, D. Madec, G. Poli, G. Prestat. Organic & Biomolecular Chemistry, 2011, 9, 8233. [IF: 3.696; Citations:7]
20. Palladium-Catalyzed Aromatic Sulfonylation: A New Catalytic Domino Process Exploiting in situ Generated Sulfinate Anions G.Le Duc, E. Bernoud, G. Prestat, S. Cacchi, G. Fabrizi, A. Iazzetti, D. Madec, G. Poli. Synlett, 2011, 20, 2943. [IF: 2.71; Citations:9]