Friedel-Crafts Coordinated Processes: Highly Selective Synthesis of Hydroxynaphthoquinones

Article abstract of DOI:10.1021/jo00056a014

Simple preparation of ethyl 3-hydroxy-1,4-naphthoquinone-2-carboxylates 2 including heterocyclic analogs is accomplished by C-regioselective bis-acylation of aromatic and heteroaromatic β-keto esters 1.Compounds 2 are readily hydrolyzed and decarboxylated to the corresponding 2-hydroxy-1,4-naphthoquinone derivatives 3.