Abstract
A series of Michael adducts (5-11) have been synthesized with good yields under solvent-free microwave conditions. Aliphatic and aromatic amines utilized as Michael donors reacted with 1(4,7-dimethoxybenzo[b]thiophen-2-yl)-2-propen-1-one (4), to produce β-aminoketones and azaheterocyclic compounds of potential biological interest.
Highlights
Introduction β-amino ketones are useful synthetic intermediates used in the synthesis of biologically active natural products and pharmaceuticals.[1,2] Classical methods for the synthesis of β-aminoketones include the Mannich reaction of methylketones with amines in the presence of paraformaldehyde, alkylation of amines with β-haloalkyl ketones, and 1,4-conjugate addition reactions with vinyl ketones and amines.[3]
HeteroMichael addition of amines to α,β- unsaturated carbonyl compounds gives β-amino ketones, which are attractive for their use as synthetic intermediates of anticancer agents, and ISSN 1551-7012
In this paper we report the synthesis in good yield of a variety of β-aminoketones of potential biological interest under environmentally friendly conditions, using microwave-supported Michael-addition
Summary
Introduction β-amino ketones are useful synthetic intermediates used in the synthesis of biologically active natural products and pharmaceuticals.[1,2] Classical methods for the synthesis of β-aminoketones include the Mannich reaction of methylketones with amines in the presence of paraformaldehyde, alkylation of amines with β-haloalkyl ketones, and 1,4-conjugate addition reactions with vinyl ketones and amines.[3]. The reaction proceeds in good yields for a variety of amides, vinyl Grignard reagents, and N-nucleophiles. In this paper we report the synthesis in good yield of a variety of β-aminoketones of potential biological interest under environmentally friendly conditions, using microwave-supported Michael-addition. This protocol includes reactions that can be conducted without solvent and in absence of metal catalysts, a highly desirable experimental condition
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