Articolo in rivista, 2009, ENG, 10.1002/ejoc.200900802

Base and Copper Catalysed Condensation of Primary Activated Nitro Compounds with enolisable Compounds

Trogu, Elena; Cecchi, Luca; De Sarlo, Francesco; Guideri, Luca; Ponticelli, Fabio; Machetti, Fabrizio

Istituto di Chimica dei Composti Organo metallici del CNR Dipartimento di Chimica Ugo Schiff dell'Università di Firenze Dipartimento di Chimica dell'Unversità di Siena

Primary nitro compounds have not been employed as nitrile oxide precursors in reactions with active methylene compounds because the reagents commonly used as dehydrating agents also react with these dipolarophiles. However, the Cull-catalysed cycloaddition/condensation procedure has been shown to be viable with these substrates, leading directly to the expected polyfunctional isoxazoles provided nitro compounds with enhanced acidity ("activated") were used. In the absence of added dipolarophiles, these nitro compounds underwent self-condensation to the corresponding furoxans. However, as well as 3,4-dibenzoylfuroxan, benzoylnitromethane predominantly gave the isomer 3-benzoyl-4-nitro-5-phenylisoxazole, the structure of which was confirmed by crystallographic analysis.

European journal of organic chemistry (Print) (34), pp. 5971–5978

Keywords

Nitro compounds, Isoxazoles, Organocatalysis, Copper, Enols

CNR authors

De Sarlo Francesco, Trogu Elena, Guideri Luca, Machetti Fabrizio

CNR institutes

ICCOM – Istituto di chimica dei composti organo metallici

ID: 16885

Year: 2009

Type: Articolo in rivista

Creation: 2010-01-29 00:00:00.000

Last update: 2013-06-20 17:43:14.000

External links

OAI-PMH: Dublin Core

OAI-PMH: Mods

OAI-PMH: RDF

DOI: 10.1002/ejoc.200900802

External IDs

CNR OAI-PMH: oai:it.cnr:prodotti:16885

DOI: 10.1002/ejoc.200900802

ISI Web of Science (WOS): 000272425400012

Scopus: 70749151512