A simple two-step synthesis of avenanthramides, constituents of oats (Avena sativa L)

Abstract

A simple two-step general procedure has been developed to prepare naturally occurring and synthetic avenanthramides, constituents of oats (Avena sativa L). Reaction of anthranilic acid I with Meldrum's acid 2 gives half amide of malonic acid 3 which on condensation with different benzaldehyde derivatives 4a-m gives avenanthramides 5a-m of which 5a-d are natural, 5e-g are their methyl ethers and 5h-m are synthetic.