Formation of γ-oxoacids and 1H-pyrrol-2(5H)-ones from α,β-unsaturated ketones and ethyl nitroacetate.
Michael addition of ethyl nitroacetate on α,β-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus prepared into 1H-pyrrol-2(5H)-ones by reaction with primary amines under Paal-Knorr conditions is also reported.
Aginagalde
Maialen
M
Kimika Fakultatea, Kimika Organikoa I Saila, Universidad del País Vasco-Euskal Herriko Uniberstitatea, Manuel de Lardizabal Etorbidea 3, 20018 San Sebastián-Donostia, Spain.
Bello
Tamara
T
Masdeu
Carme
C
Vara
Yosu
Y
Arrieta
Ana
A
Cossío
Fernando P
FP
D000085:Acetates / Q000737:chemistry*; D000143:Acids / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
D000085:Acetates; D000143:Acids; D007659:Ketones; D009574:Nitro Compounds; D011758:Pyrroles; C555739:ethyl nitroacetate; D010100:Oxygen