A Base-Catalyzed Domino-Isomerization–Hydroamination Reaction—A New Synthetic Route to Amphetamines

An efficient synthesis of pharmaceutically interesting amphetamines by a base-catalyzed domino-isomerization–hydroamination reaction is presented. Starting from allylbenzene and various primary or secondary amines, the basic structural pattern of amphetamines is synthesized directly in yields of up...

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Bibliographic Details
Published in:Tetrahedron 2000-07, Vol.56 (29), p.5157-5162
Main Authors: Hartung, Christian G., Breindl, Claudia, Tillack, Annegret, Beller, Matthias
Format: Article
Language:English
Subjects:
amphetamines
base-catalysis
domino-isomerization–amination reaction
hydroamination
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Summary:An efficient synthesis of pharmaceutically interesting amphetamines by a base-catalyzed domino-isomerization–hydroamination reaction is presented. Starting from allylbenzene and various primary or secondary amines, the basic structural pattern of amphetamines is synthesized directly in yields of up to 91% in the presence of catalytic amounts of n-butyllithium.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00436-1