A Straightforward and Efficient Method for the Synthesis of Diversely Substituted β-Aminoketones and γ-Aminoalcohols from 3-( N,N -Dimethylamino)propiophenones as Starting Materials
2013; Brazilian Chemical Society; Linguagem: Inglês
10.5935/0103-5053.20130177
ISSN1678-4790
AutoresRodrigo Abonı́a, Danny Arteaga, Juan‐Carlos Castillo, Braulio Insuasty, Jairo Quiroga, Alejandro Ortíz,
Tópico(s)Chemical synthesis and alkaloids
ResumoLibraries of novel β-aminoketones and γ-aminoalcohols showing a wide structural diversity were easily obtained from a simple approach, using 3-(N,N-dimethylamino)propiophenone derivatives as key starting material. The procedure involved initially an N-alkylation of secondary benzylamines with propiophenone salts yielding the desired β-aminoketones. Chemical or catalytic reduction of their carbonyl groups provided the final γ-aminoalcohols in good yields. This protocol proved to be convenient as an alternative route for the synthesis of the local anesthetic Falicain® and for the topic antifungal drug Naftifine®.
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