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Title: Catalytic Condensation of Nitro Compounds with Alkenes and Alkynes: a New Method for Molecular Functionalisation

Principal Investigator: Fabrizio Machetti

Project type: National

Duration: 01/2019-12/2020

Abstract: The isoxazole skeleton represents a privileged structure for the design of biologically active molecules and new functionalised materials. We have recently developed a synthetic procedure for the catalysed preparation of isoxazoles from primary nitro compounds and alkenes or alkynes. We established that a catalytic amount of a suitable base was enough to promote condensation between primary nitro compounds and alkenes or alkynes. Condensation occurs in chloroform as well as in hydroxylic solvents including water. In chloroform the catalytic effect depend on the nature of the base and can be improved combining the base with a metal, while in water any base, either organic or inorganic, has the same catalytic effect. The above catalytic method has been referred to as the Machetti- De Sarlo reaction. The project consists in studying and applying this process i) in the conjugation of peptide substrates containing in a side chain propargylic residues ii) in the functionalisation of carbon nanotubes (including fullerene) for the preparation of materials with specific and particular properties due to the inserted molecular structures.

Partnership: ICCOM-CNR, Dipartimento di Chimica “Ugo Schiff”, Università di Firenze.

ICCOM participants: Fabrizio Machetti, Giovanni La Penna

Sponsored by: Cassa di Risparmio di Firenze Foundation

Financial contribution (overall): 30.000 €

Financial contribution (ICCOM): 7.500 €

Categories: Ended projects