V. Pace, F. Martinez, M. Fernandez, J.V. Sinisterra, A.R. Alcantara.Full Paper
Advanced Synthesis and Catalysis, 2009, 18, 3199-3126.
- Biotransformations Group, Department of Organic and Pharmaceutical Chemistry, Pharmacy Faculty, Complutense University, Plaza Ramón y Cajal s/n, 28040 Madrid, Spain, Fax: (+34)-91-394-1820
- Industrial Biotransformations Service (SBI), Scientific Park of Madrid (PCM), C/Santiago Grisolía 2, 28760 Tres Cantos, Madrid, Spain
Correspondence to Andrés R. Alcántara, Biotransformations Group, Department of Organic and Pharmaceutical Chemistry, Pharmacy Faculty, Complutense University, Plaza Ramón y Cajal s/n, 28040 Madrid, Spain, Fax: (+34)-91-394-1820 email: Andrés R. Alcántara (andresr@farm.ucm.es)
Funded by:
CAM (Comunidad Autónoma de Madrid, QO-UCM); Grant Number: S-0505/PPQ/0344
MEC (Ministerio de Educación y Ciencia); Grant Number: CTQ2006-09052
Ministerio de Ciencia e Innovación; Grant Number: FPU-AP-2005-5112
Keywords
amines • halogenation • ketones • oxidation • protecting groups
Abstract
The oxidative hydrolysis of different trifluoroacetyl-protected N-(2-chloroallyl)anilines, promoted by calcium hypochlorite, is able to yield several not previously described -arylamino--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.
http://dx.doi.org/10.1002/adsc.200900565
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