Synthesis of Tritylones via Cascade Reaction of Arynes with 5-Ethoxyoxazoles.

Abstract

A cascade reaction involving arynes and 5-ethoxyoxazoles has been developed toward the synthesis of 9-alkyl/aryl tritylones. 5-Ethoxyoxazoles undergo a [4 + 2] cycloaddition reaction with arynes followed by retro-[4 + 2] cycloaddition, a second intermolecular [4 + 2] cycloaddition reaction, and hydrolytic ring cleavage to generate substituted tritylones in good yields. The conversion of tritylone products to a series of spirocyclic anthrone derivatives has been demonstrated. The reaction is expeditious, exhibits wide scope, and employs readily available starting materials.