Abstract
An efficient method has been developed for the synthesis of β-enaminones under solvent-free reaction conditions using PPA-SiO2 as catalyst. The reaction yields were good to excellent (up to 90%). This methodology affords high selectivity and good tolerance of a variety of different functional groups present on both aromatic and aliphatic amines. In addition, the methodology is environmentally benign and cost-effective due to absence of solvent and easy work-up.
Highlights
Enaminones are chemical compounds including an amino group coupled through a C=C bridge to a carbonyl group
When the reaction was carried out under solvent free condition, both yield and reaction time were significantly improved at about 70 °C
To a mixture of dicarbonyl compound and 1,2-diaminomethanephenylene (1 mmol, 0.14 mL) PPA-SiO2 (110 mg/mmol) was added in in one lot and the resulting yellow mixture was stirred at 70–80 °C for the specified time shown in the Table 3
Summary
Enaminones are chemical compounds including an amino group coupled through a C=C bridge to a carbonyl group They are versatile synthetic intermediates [1,2,3] that combine the ambident electrophilicity of an enone with the ambident nucleophilicity of an enamine. Enaminones are important building blocks in organic synthesis which can be further transformed into valuable bioactive nitrogen heterocylces [4,5,6], natural therapeutic agents and alkaloids [5,6]. Enaminones are known to affect several physiological functions themselves or are precursors for such molecules, in particular as anticonvulsant [16], anti-epileptic [17], anti-inflammatory [18] and antitumor agents [19,20,21]
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