- Journal of the Turkish Chemical Society Section A: Chemistry
- Vol: 9 Issue: 2
- Cyclization Reactions of Non-Conjugate Ynones with Propargyl Amine in the Presence of a Catalyst
Cyclization Reactions of Non-Conjugate Ynones with Propargyl Amine in the Presence of a Catalyst
Authors : Volkan Taşdemir
Pages : 553-570
Doi:10.18596/jotcsa.1064488
View : 11 | Download : 5
Publication Date : 2022-05-31
Article Type : Research
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