Multicomponent Synthesis of Functionalized Tetrahydroacridinones: Insights into a Mechanistic Route.
A mechanistic study of three-component reactions of various aromatic amines with a number of aldehydes and 1,3-diones was achieved. The unprecedented reaction involved a nucleophilic attack of an aromatic amine on the in situ generated Michael adduct intermediate followed by six-electron ring cyclizations. It is contrary to the common belief that advocates involvement of coupling reactions between a Knoevenagel adduct and an aromatic amine to deliver substituted tetrahydroacridinones.
Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
Tsai-Wen
TW
Chung
Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
Bharat D
BD
Narhe
Department of Chemistry, National Tsing Hua University , Hsinchu 300, Taiwan.
Chun-Cheng
CC
Lin
Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.|Department of Medicinal and Applied Chemistry, Kaohsiung Medical University , 100 Shih-Chuan First Road, Kaohsiung 807-08, Taiwan.
Chung-Ming
CM
Sun