Hydrolysis of dihydroisoquinoline derivatives activated by sulfonyl or acyl chloride

Abstract

A new, efficient, and mild strategy for hydrolysis of 3,4-dihydroisoquinoline imines activated by sulfonyl chloride or acyl chloride has been developed, by which method ketosulfonamides and ketoamides have been synthesized. This process tolerates broad scope with respect to both the sulfonyl chloride and acyl chloride with moderate to excellent yields. This protocol features a broad substrate scope for various kinds of 3,4-dihydroisoquinoline and mild reaction conditions without using strong acidic or basic conditions. These features show that this user-friendly and simple system could be applied in the future to the synthesis of a broader range of amino benzophenones.