One-Pot Synthesis of 2-R-Naphtho[2,3-b]thiophene-4,9-diones via Cyclization of 2-(R-Ethynyl)-1,4-naphthoquinones with Na2S2O3

The concise and efficient one-pot synthesis of 2-R-naphtho[2,3-b]thiophene-4,9-diones from 2-bromo-1,4-naphthoquinone and alkynes has been developed. The reaction proceeds through the formation of 2-(R-ethynyl)-1,4-naphthoquinones, which undergo transformation with Na2S2O3 to 2-R-naphtho[2,3-b]thiophene-4,9-diones via C-H sulfuration, accompanied by the formation of the aromatic Bunte salt, followed by its air oxidation and 5-endo-dig cyclization. The protocol is characterized by simplicity, good tolerance for functional groups, relatively mild conditions, and commercially available starting compounds.

Automated summary

The method described in this study efficiently synthesizes 2-R-naphtho[2,3-b]thiophene-4,9-diones via a series of reactions starting from 2-bromo-1,4-naphthoquinone and alkynes. The protocol offers mild reaction conditions, good functional group tolerance, and readily available starting materials.