1,4-Diazabicyclo[2.2.2]octane (DABCO) as an Efficient Reagent for the Synthesis of Isoxazole Derivatives from Primary Nitro Compounds and Dipolarophiles: The Role of the Base
Luca Cecchi, Francesco De Sarlo*, Fabrizio Machetti*
*Dipartimento di Chimica Organica U. Schiff, Università di Firenze, Via
della Lastruccia 13, 50019 Sesto Fiorentino - Firenze, Italy, Email:
francesco.desarlo
unifi.it, fabrizio.machettiunifi.it
L. Cecchi, F. De Sarlo, F. Machetti, Eur. J. Org. Chem., 2006, 4852-4860.
DOI: 10.1002/ejoc.200600475
Abstract
The dehydration of primary nitro compounds can be performed by bases in the presence of dipolarophiles. Among the organic bases examined, DABCO gave the best results. The reaction is applicable to activated nitro compounds and to phenylnitromethane and affords isoxazoline derivatives in higher yields compared with those of other methods. The reaction, however, is not compatible with nitroalkanes.
see article for more examples
proposed mechanism
Key Words
1,3-dipolar cycloaddition, DABCO, Nitro Compounds, Isoxazolines, Isoxazoles
ID: J24-Y2006-3650
