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Quadrelli Paolo

Qualifica:
Professore associato
Ricevimento:
Mercoledì; 10.00-11.00
E-mail:
paolo.quadrelli (at) unipv.it
Telefono:
+39.0382.987315
Fax:
+39.0382.987323
Sito web:
https://mitch.unipv.it:4443/uri/public?lingua=ITA&cr=I29566
Dipartimento:
Dipartimento di Chimica

Elenco corsi

2012/2013
Chimica organica e biochimica
2012/2013
Chimica Organica e laboratorio

+ Altri anni accademici

2011/2012
Chimica organica e biochimica
2011/2012
Chimica Organica e laboratorio
2010/2011
Chimica Bioorganica e Bioanalitica
2010/2011
Chimica Organica e laboratorio
2009/2010
Chimica Organica e laboratorio
2008/2009
Chimica Organica applicata e laboratorio
2008/2009
Chimica Organica I con laboratorio
2007/2008
Chimica Organica applicata e laboratorio

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Curriculum

Il Prof. Paolo QUADRELLI si è laureato in Chimica presso l'Università di Pavia nel 1986 ed ha conseguito il titolo di Dottore di Ricerca in Scienze Chimiche (III Ciclo) presso la medesima Università nel 1990. Dal 1990 al 1992, ha svolto attività di ricerca presso i laboratori della Società Eniricerche S.p.A (attualmente Enitecnologie S.p.A.) in San Donato Milanese (MI). Dal 1992 è Ricercatore presso il Dipartimento di Chimica Organica della Facoltà di Scienze MM.FF.NN. dell'Università di Pavia. Dal Novembre 1996 all'Ottobre 1997 ha svolto attività di ricerca presso la School of Chemistry dell'Università di Leeds (Gran Bretagna) presso il gruppo di ricerca del Prof. Ronald Grigg (Marie Curie Fellowship Grant). I suoi interessi scientifici riguardano il chimismo di nitrilossidi e nitrilimmine e lo studio delle cicloaddizioni a sistemi eteroaromatici. Gli studi sul chimismo dei nitrilossidi hanno fornito metodi alternativi per la generazione degli intermedi nitrosocarbonilici per blanda ossidazione di nitrilossidi o, alternativamente, per cicloreversione termica e fotochimica di 1,2,4-ossadiazoli-4-ossidi, una classe di eterocicli che è stata oggetto di una recente rassegna. A partire dagli addotti dienici dei nitrosocarbonili è stato messo a punto un nuovo approccio alla sintesi di nucleosidi carbociclici modificati con potenziale attività anti-virale. Svolge anche ricerche di natura teorica per l'individuazione dei fattori determinanti le varie forme di selettività delle cicloaddizioni con l'uso di metodi DFT. Tra gli altri interessi di ricerca vi è poi l'uso di metalli di transizione per la sintesi di complessi chirali da utilizzare quali catalizzatori in reazioni di cicloaddizione enantioselettive nonché la sintesi organica in fase solida applicata alle reazioni pericicliche come valida metodologia per la salvaguardia ambientale. Queste ricerche sono state oggetto di diverse comunicazioni a congressi nazionali ed internazionali. Ha svolto numerose attività organizzative: dal 1997 al 2002 è stato Addetto Locale al Servizio di Prevenzione e Protezione del Dipartimento di Chimica Organica e dal 1999 al 2003 è stato Rappresentante dei Docenti per i temi della Sicurezza presso l'Ateneo Pavese. Questi temi sono oggetto di attività didattica per la Scuola Interuniversitaria Lombarda di Specializzazione per l'Insegnamento Secondario (SILSIS) a partire dal 2002. E' stato membro in rappresentanza del Dipartimento di Chimica Organica della Commissione del Consiglio Didattico in Scienze e Tecnolgie Chimiche per i Fondi Didattici d'Ateneo e membro della Commissione FAR per il settore Chimica Organica. E' membro della Commissione Paritetica del Consiglio Didattico in Scienze e Tecnologie Chimiche. L'attività didattica è stata svolta dal Prof. Quadrelli interamente nell'ambito dei Corsi di Laurea in Scienze e Tecnologie Chimiche dal 1997 ed attualmente è incaricato del corso di Chimica Organica Applicata e Laboratorio (9 CFU), esame fondamentale del 3° anno del CL in Tecnologie Chimiche per l'Ambiente e le Risorse.

 

 

 

 

Prof. Paolo Quadrelli got the Degree in Chemistry in 1986 at the University of Pavia and the PhD Degree in Chemical Sciences in 1990 at the same University. From 1990 to 1992 he worked in the R&D Laboratories of Eniricerche S.p.A. (actually Enitecnologie S.p.A.) in San Donato Milanese (MI). Since 1992 he is assistent professor at the Department of Organic Chemistry in the Faculty of Sciences of the University of Pavia. From November 1996 to October 1997 Prof. Quadrelli joined the School of Chemistry at the University of Leeds (UK) working in the research group of prof. Ronald Grigg (Marie Curie Fellowship Grant). His scientific interests concern the chemistry of nitrile oxides and imines and the study of the cycloadditions to heteroaromatic systems. The studies on the chemistry of nitrile oxides allowed to suggest a new methodology to generate nitrosocarbonyl intermediates through the mild oxidation of nitrile oxides or, alternatively, the thermic and photochemical cycloreversion of 1,2,4-oxadiazoles-4-oxides, a class of heterocycles which have been subject of a recent review. From the hetero Diels-Alder cycloadducts of nitrosocarbonyls, a new approach has been developed toward modified carbocyclic nucleosides with potential anti-viral activity. He is also involved in theoretical studies on the factors determining the selectivities in cycloaddition reactions with the help of DFT methods. Among the other research activities, the use of transition metals for the synthesis of chiral complexes has been also developed to be employed for enantioselective catalised cycloaddition reactions as well as the solid phase organic synthesis applied to pericyclic reactions as a valuable environmental friendly methodology. All these researches have been communicated to several national and international conferences. Among his activities as organiser: from 1997 to 2002 he was Safety Officer of the Department of Organic Chemistry and since 1999 member of the Safety Commission of the University. He holds the course of Safety in Laboratory at the School of Teaching of Lombardy (SILSIS) since 2002. He was also member of the University Didactic Funds Commitee for the Chemical Area as well as of the FAR Commission. Actually he is member of the Didactic Commission for the School of Chemistry. Since 1997 Prof. Quadrelli was involved in teaching in the Chemical Sciences courses and actually has a docent position for the course of Applied Organic Chemistry and Laboratory (9 CFU) for the CL of Tecnologie Chimiche per l'Ambiente e le Risorse.

Temi di ricerca

Synthesis and reactivity of nitrogen heterocyclic compounds. The synthesis and reactivity of pyrazoles, isoxazoles and oxadiazoles is a traditional research topic of the research unit. Recent studies involve the thermal or photochemical fragmentation of 1,2,4-oxadiazole-4-oxides.

1,3-Dipolar cycloadditons of nitrile oxides and nitrile imines. The 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrile imines are currently studied in order to determine the factors determining the selectivity outcome, and in particular the role of steric effects in the reactions with a,b-unsaturated carbonyl compounds. The cycloadditon of nitrile oxides and imines to pyridines are also studied allowing for the assesment of one and two-step cycloadditions.

Generation, reactivity and synthetic applications of nitrosocarbonyl intermediates. The oxidation of nitrile oxides with tertiary amine N-oxides affords nitrosocarbonyl intermediates which can be trapped with dienes or enes. Starting from the cycloadducts of nitrosocabonyls to cyclopentadiene and cyclohexadiene, a straightforward synthesis of stereodefine aminols has been accomplished as well as their synthetic elaboration into carbocyclic nucleosides.

Solid phase synthesis through 1,3-dipoles. Nitrile oxides have been found stable for days when generated on a Merrifield or a Wang resin. This stability allows for their clean and efficient oxidation into nitrosocarbonyl intermediates. With the same approach, supported 1,2,4,-oxadiazole-4-oxides are obtainable and their photochemical cleavage on solid phase offers a clean and valuable method for the generation of nitrosocabonyls.

Pubblicazioni

 
1)             A. Corsico Coda, G. Desimoni, P. Quadrelli, P.P. Righetti e G. Tacconi
“Copper (II) in Organic Synthesis. V. Influence of the nature of Copper (II) complexes of 3-arylaminomethyleneoxindoles on their reactivity with dimethyl acetylenedicarboxylate”
Gazz. Chim. Ital. 1987, 117, 301.
2)             A. Corsico Coda, G. Desimoni, A. Gamba Invernizzi, P. Quadrelli, P.P. Righetti e G. Tacconi
“Copper (II) in Organic Synthesis. VI. Reaction of the of Copper (II) acetate complex of 1-methylisatin-3-chlorophenylhydrazone with dimethyl acetylenedicarboxylate”
          Tetrahedron 1987, 43, 2843.
3)             A. Corsico Coda, G. Desimoni, H. L. Monaco, P. Quadrelli e P.P. Righetti
“Copper (II) in Organic Synthesis. VII. Copper (II) acetate-catalyzed reaction of 1-acetyl-3-(chlorophenyl)hydrazonoisatin with dimethyl acetylenedicarboxylate”
          Gazz. Chim. Ital. 1989, 119, 13.
4)             G. Desimoni, P. Quadrelli e P.P. Righetti
“Copper (II) in Organic Synthesis. VIII. Enantioselective Michael reactions with chiral copper (II) complexes as catalysts”
          Tetrahedron 1990, 46, 2927.
5)             G. Desimoni, A. Gamba Invernizzi, P. Quadrelli e P.P. Righetti
“Copper (II) in Organic Synthesis. IX. The Copper (II) catalyzed michael reaction as a route to polysubstituted benzene derivatives”
          Gazz. Chim. Ital. 1991, 121, 483.
6)             P. Quadrelli, C. Flego, A. Gervasini e M. G. Clerici
          “Superacidic catalyst and process for preparing it”
          Eur. Patent 0 520 543, 1992; CA 118: 256982, 1993.
7)             G. Desimoni, G. Dusi, G. Faita, P. Quadrelli e P.P. Righetti
“Copper (II) in Organic Synthesis. XI. Evaluation of the ligand architecture on the efficiency of a Copper (II) catalyst for enantioselective Michael reactions ”
          Tetrahedron 1995, 51, 4131.
8)             P. Caramella, A. Gamba Invernizzi, E. Pastormerlo, P. Quadrelli e A. Corsaro
          “A pericyclic cascade in the addition of diphenylnitrile imine to pyridine”
          Heterocycles 1995, 40, 515.
9)             P. Quadrelli, A. Gamba Invernizzi e P. Caramella
          “A mild oxidation of nitrile oxides: a new synthetic route to nitroso carbonyl intermediates”
          Tetrahedron Lett. 1996, 37, 1909.
10)         A. Corsaro, G. Perrini, V. Pistarà, P. Quadrelli, A. Gamba Invernizzi e P. Caramella
“Cycloaddition of Benzonitrile Oxide to Pyridazine, Pyrimidine and Pyrazine”
          Tetrahedron, 1996, 52, 6421.
11)         P. Quadrelli, A. Gamba Invernizzi, M. Falzoni e P.Caramella
“Cycloaddition of Nitrile Oxide to Amidoximes. A General Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazole-4-oxides”
Tetrahedron, 1997, 53, 1787.
12)         P. Quadrelli, M. Mella e P. Caramella
          “Nitrosocarbonyl Intermediates as Super-Enophiles: a Mild Method for Carbon-Nitrogen Bond Formation”
Tetrahedron Lett. 1998, 39, 3233.
13)         P. Quadrelli, M. Mella e P. Caramella
“A Photochemical Generation of Nitrosocarbonyl Intermediates”
Tetrahedron Lett. 1999, 40, 797.
14)         P. Caramella, D. Reami, M. Falzoni e P. Quadrelli
          “Cycloaddition of nitrile oxides to cyclic and acyclic a,b-unsaturated amides. Frontier orbital interactions and an unexpected steric drift determine regiochemistry”
          Tetrahedron 1999, 55, 7027.
15)         P. Quadrelli, M. Mella, A. Gamba Invernizzi e P.Caramella
“The mild oxidation of nitrile oxides affords a convenient entry to nitrosocarbonyl intermediates, versatile tools in organic syntheses”
          Tetrahedron, 1999, 55, 10497.
16)         G. Faita, A. Paio, P. Quadrelli, F. Rancati e P. Seneci
“(4S)-p-Hydroxybenzyl-1,3-oxazolidin-2-ones as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions”
          Tetrahedron Lett. 2000, 41, 1265.
17)         P. Quadrelli, G. Campari, M. Mella e P. Caramella
          “A thermal fragmentation of 1,2,4-oxadiazole-4-oxides to nitriles and nitrosocarbonyls”
          Tetrahedron Lett. 2000, 41, 2019.
18)         P. Quadrelli, M. Mella, P. Paganoni e P. Caramella
          “Cycloadditions of Nitrile Oxides to the Highly Reactive N-Acyl 2-Oxa-3-Azanorborn-5-enes Afford Versatile Cycloadducts and a Convenient Entry to Highly Functionalized Derivatives”
          Eur. J. Org. Chem. 2000, 2613.
19)         L. Toma, P. Quadrelli, G. Perrini, R. Gandolfi, C. Di Valentin, A. Corsaro e P. Caramella
“Cycloadditions of Nitrile Oxides to a,b-Unsaturated Aldehydes. Frontier Orbital Interactions and Secondary Orbital Interactions at Work in Determining Regiochemistry”
          Tetrahedron 2000, 56, 4299.
20)         L. Toma, P. Quadrelli e P. Caramella
“Classical and non-classical secondary orbital interactions and Coulombic attraction in regiospecific dimerization of acrolein”
Tetrahedron Lett. 2001, 42, 731.
21)         L. Toma, S. Romano, P. Quadrelli e P. Caramella
“Merging of 4+2 and 2+4 cycloaddition paths in the regiospecific dimerization of methacrolein. A case of concerted crypto-diradical cycloaddition”
          Tetrahedron Lett. 2001, 42, 5077.
22)         G. Faita, A. Paio, P. Quadrelli, F. Rancati e P. Seneci
“Solid supported chiral auxiliaries in asymmetric synthesis. Part 2: Catalysis of 1,3-dipolar cycloadditions by Mg(II) cation”
          Tetrahedron 2001, 57, 8313.
23)    P. Caramella, P. Quadrelli, L. Toma
“An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene”
J. Am. Chem. Soc. 2002, 124, 1130.
24)         G. Faita, M. Mella, A. Mortoni, A Paio, P. Quadrelli, P. Seneci
“Solid supported nitrile oxides as stable and valuable reactive intermediates”
Eur. J. Org. Chem. 2002, 1175.
25)         G. Desimoni, G. Faita, A. Galbiati, D. Pasini, P. Quadrelli, F. Rancati
“A soluble polymer-bound Evans’ chiral auxiliary: synthesis characterization and use in cycloaddition reactions”
Tetrahedron Asymmetry 2002, 13, 333.
26)         P. Quadrelli, V. Fassardi, A. Cardarelli, P. Caramella
“Intra- and Intermolecular Hydrogen Bonding Effects in Cycloadditions between Nitrile Oxides and 4-Benzoylamino-2-cyclopenten-1-ol and its Derivatives”
Eur. J. Org. Chem. 2002, 2058.
 
27)         P. Quadrelli, S. Romano, L. Toma, P. Caramella
“Merging and bifurcation of 4+2 and 2+4 cycloaddition modes in the archetypal dimerization of butadiene. A case of competing bispericyclic and diradical paths”
Tetrahedron Lett. 2002, 43, 8785.
28)         L. Toma, P. Quadrelli, W. H. Bunnelle, D. J. Anderson, M. D. Meyer, G. Cignarella, A. Gelain, D. Barlocco
“6-Chloropyridazin-3-yl Derivatives Active as Nicotinic Agents: Synthesis, Binding and Modelling Studies”
J. Med. Chem., 2002, 45, 4011
29)         P. Quadrelli, Silvano Romano, Lucio Toma, Pierluigi Caramella
“A bispericyclic Transition Structure allows for efficient relief of antiaromaticity enhancing reactivity and endo stereoselectivity in the dimerization of the fleeting cyclopentadienone”
J. Org. Chem., 2003, 68, 6035
30)         G. Desimoni, G. Faita, P. Quadrelli
“Pyridine-2,6-bis(oxazolines), Helpful Ligands for Asymmetric Catalysts”
Chem. Rev. 2003, 103, 3119.
31)         B. Bovio, P. Quadrelli
“Crystal structure of 1-phenylamino-2-phenyl-4-p-chlorophenylimidazole, C21H16N3Cl”
J. Chem. Crystallography, 2003, 33, 913.
32)         P. Quadrelli, R. Scrocchi, P. Caramella, A. Rescifina, A. Piperno
“From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through nitrosocarbonyl chemistry”
Tetrahedron 2004, 60, 3643.
33)         U. Chiacchio, F. Genovese, D. Iannazzo, A. Piperno, P. Quadrelli, A. Corsaro, R. Romeo, V. Valveri, A. Mastino
“4’-a-C-Branched N,O-Nucleosides: Synthesis and Biological Properties”
Bioorganic. Med. Chem., 2004, 12, 3903.
34)         B. Bovio, P. Quadrelli
“Crystal structure of 4-(6-chloro-purin-9-yl)-3-phenyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazol-6-ol, C17H14N5O2Cl”
J. Chem. Crystallography, 2005, 35, 701.
35)         B. Bovio, P. Quadrelli, P. Caramella
“Crystal structure and DFT calculations of 3,8–Diphenyl–3a,4,5,5a,8a,8b–hexahydro–benzo[1,2–d: 3,4–d’]diisoxazole, C20H18N2O2
J. Mol. Struct., 2005, 743, 135.
36)         P. Caramella, P. Quadrelli, L. Toma, S. Romano, K. S. Khuong, B. Northrop, K. N. Houk
The three corrugated surfaces of 1,4-divinyltetramethylene diradical intermediates and their connections to 1,2-divinylcyclobutane, 4-vinylcyclohexene, 1,5-cyclooctadiene, and two Butadienes
J. Org. Chem., 2005, 70, 2994.
37)         P. Quadrelli, R. Scrocchi, A. Piccanello, P. Caramella
“Photochemical generation of nitrosocarbonyl intermediates on solid phase: synthons toward hetero Diels-Alder and ene adducts through photocleavage”
J. Comb. Chem. 2005, 7, 887.
38)         P. Quadrelli, A. Piccanello, N. Vazquez Martinez, B. Bovio, M. Mella, P. Caramella
“Isoxazoline-carbocyclic aminols for nucleoside synthesis throguh aza-Diels-Alder reactions”
Tetrahedron 2006, 62, 7370.
39)         P. Quadrelli, M. Mella, S. Carosso, B. Bovio, P. Caramella
“A straightforward synthesis of isoxazoline-based carbocyclic nucleosides from 1,3-cyclohexadiene through nitrosocarbonyl chemistry”
Eur. J. Org. Chem. 2007, 6003.
40)         P. Quadrelli, P. Caramella
“Synthesis and synthetic application of 1,2,4-oxadiazole-4-oxides”
Curr. Org. Chem. 2007, 11, 959.
41)         P. Quadrelli, M. Mella, A. Piccanello, S. Romano, P. Caramella
“Variable Markonikov orientation and “cis effect” in ene reactions of nitrosocarbonyl intermediates”
J. Org. Chem. 2007, 72, 1807.
42)         P. Quadrelli, A. Piccanerllo, M. Mella, A. Corsaro, V. Pistarà
“From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through aza-Diels-Alder reactions”
Tetrahedron 2008, 64, 3541.

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