Expedient stereoselective synthesis of trifluoromethylated pyranonaphthoquinones

Dang Thi Tuyet Anh, Hoang Thi Phuong, Vu Ngoc Doan, Pham The Chinh, Nguyen Thanh Ha, Nguyen Thi Thu Ha, Nguyen Hung Huy, Ngo Quoc Anh, Nguyen Van Tuyen

Abstract


Stereodefined and biologically relevant CF3-containing hydroxypyranonaphthoquinone carboxylates were prepared for the first time by a one-pot four-component condensation between 2-hydroxy-1,4-naphthoquinone, an aldehyde, ethyl 4,4,4-trifluoroacetoacetate and ammonium acetate. This transformation is presumed to proceed via aldol condensation/Mannich reaction followed by Michael addition and regio- and stereoselective 6-exo-trig cyclization, deamination and addition of water.

Keywords. Hydroxypyranonaphthoquinone, ammonium acetate.


Keywords


Hydroxypyranonaphthoquinone, ammonium acetate