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Chemoselective Synthesis of 5‐Alkylamino‐1 H ‐pyrazole‐4‐carbaldehydes by Cesium‐ and Copper‐Mediated Amination
Author(s) -
OrregoHernández Jessica,
Cobo Justo,
Portilla Jaime
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500505
Subject(s) - amination , chemistry , pyrazole , caesium , copper , nucleophilic substitution , combinatorial chemistry , catalysis , aryl , medicinal chemistry , organic chemistry , alkyl
Microwave‐assisted synthesis of new 5‐alkylamino‐pyrazole‐4‐carbaldehydes was performed efficiently, with yields up to 99 % and short reaction times. Nucleophilic substitution of primary alkylamines with activated 5‐chloro‐1‐(2‐pyridyl)pyrazole‐4‐carbaldehyde was mediated by the “cesium effect”. The amination of deactivated 1‐aryl‐5‐chloropyrazole‐4‐carbaldehydes was also assisted by the cesium ion and catalyzed by copper(I).