A multicomponent approach to the synthesis of 1,3-dicarbonylic compounds.
A general synthesis of 1,3-dicarbonylic compounds using multicomponent reactions of isocyanides is described. The process involves a Passerini three-component condensation of glyoxal derivatives, isocyanides and acetic acid, followed by metal mediated reductive or solvolytic removal of the acid component. Noteworthy, reductive deacetoxylation of Passerini glyoxylamide adducts was successfully achieved using photochemically activated SmI(2). This procedure constitutes a novel convenient method for the direct synthesis of malonic retro-peptidic subunits.
Neo
Ana G
AG
Laboratorio de Química Orgánica y Bioorgánica (L.O.B.O.), Departamento de Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071, Cáceres, Spain.
Carrillo
Rosa M
RM
Delgado
Jose
J
Marcaccini
Stefano
S
Marcos
Carlos F
CF
D020650:Combinatorial Chemistry Techniques; D003998:Dicarboxylic Acids / Q000138:chemical synthesis*; D008314:Malonates / Q000138:chemical synthesis
D003998:Dicarboxylic Acids; D008314:Malonates; C008314:malonamide
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