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Highly Efficient Synthesis of New α‐Arylamino‐α′‐chloropropan‐2‐ones via Oxidative Hydrolysis of Vinyl Chlorides Promoted by Calcium Hypochlorite
Author(s) -
Pace Vittorio,
Martínez Fernando,
Fernández María,
Sinisterra José V.,
Alcántara Andrés R.
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900565
Subject(s) - chemistry , calcium hypochlorite , hydrolysis , hypochlorite , yield (engineering) , oxidative phosphorylation , calcium , organic chemistry , oxidizing agent , combinatorial chemistry , chlorine , biochemistry , materials science , metallurgy
The oxidative hydrolysis of different trifluoroacetyl‐protected N ‐(2‐chloroallyl)anilines, promoted by calcium hypochlorite, is able to yield several not previously described α‐arylamino‐α′‐chloropropan‐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.