Highly Efficient Synthesis of New α-Arylamino-α'-chloropropan-2-ones via Oxidative Hydrolysis of Vinyl Chlorides Promoted by Calcium Hypochlorite

摘要

The oxidative hydrolysis of different tri-fluoroacetyl-protected N-(2-chloroallyl)anilines, promoted by calcium hypochlorite, is able to yield several not previously described α-arylamino-α'-chloro-propan-2-ones, very valuable building blocks that are useful as precursors of several drugs, in excellent yields and short reaction times. The main requirement of the reaction for avoiding the undesired aromatic chlorination (N-protection) is effectively solved by the use of the easily formed and removed N-trifluoroacetyl group. Thus, it is possible to perform the oxidative hydrolysis-deprotection step using a one-pot strategy, obtaining quantitative yields in very short reaction times.