Cyclization Reactions of Non-Conjugate Ynones with Propargyl Amine in the Presence of a Catalyst

Abstract

In this study, acetate derivatives were obtained from the reaction of acetophenones using diethyl carbonate. The acidic proton of CH2 moiety was abstracted using a suitable base and α-propargyl-β-ketoester (non-conjugated ynone) derivatives 3a-c were obtained from the reaction of the acetate derivatives with propargyl bromide. By removing the ester group of α propargyl-β-ketoester derivatives under suitable conditions, α-propargyl acetophenones (non-conjugated ynone) 4a-c were obtained. In this study, 6 different unconjugated ynone derivatives were synthesized as starting material with yield in a range of 60-95%. Cyclization reactions with propargyl amine in the presence of three different unconjugated ynone derivatives, metal catalysts were investigated. The synthesis of propargyl pyrroles 7a-c having substituents on C-2 and C-5 was completed.

Keywords

• Cyclization
• Propargyl amine
• Pyrrole
• Unconjugated ynone

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