THE REACTION OF THE DIANION OF BETA-ENAMINOKETONES WITH ELECTROPHILES.6. SYNTHESIS OF GAMMA'-NITRO-BETA-ENAMINOKETONE AND EPSILON-NITRO-BETA-ENAMINOKETONE

Authors
BARTOLI G BOSCO M DALPOZZO R DENINO A PALMIERI G
Citation
G. Bartoli et al., THE REACTION OF THE DIANION OF BETA-ENAMINOKETONES WITH ELECTROPHILES.6. SYNTHESIS OF GAMMA'-NITRO-BETA-ENAMINOKETONE AND EPSILON-NITRO-BETA-ENAMINOKETONE, Tetrahedron, 50(32), 1994, pp. 9831-9836
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
32
Year of publication
1994
Pages
9831 - 9836
Database
ISI
SICI code
0040-4020(1994)50:32<9831:TROTDO>2.0.ZU;2-O
Abstract
alpha'- And gamma-dianions of acyclic beta-(monoalkylamino)-alpha,beta -unsaturated ketones can attack the double bond of nitroalkenes afford ing gamma'- and epsilon-nitro-beta-enaminoketones in good to high yiel ds. In contrast to the corresponding 1,3-dicarbonyl dianions, cyclic p roducts from intramolecular Henry reactions are never observed. Quench ing the reaction with sulphuric acid epsilon-nitro-beta-enaminoketones are converted in low yields into dihydropyrroles.