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Organocatalytic 1,3‐Dipolar Cycloaddition Reaction of β‐Keto Amides with Azides – Direct Access to 1,4,5‐Trisubstituted 1,2,3‐Triazole‐4‐carboxamides
Author(s) -
Zhou Xiao,
Xu Xianhong,
Liu Kun,
Gao Hua,
Wang Wei,
Li Wenjun
Publication year - 2016
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.201600157
Subject(s) - chemistry , amide , azide , 1,3 dipolar cycloaddition , cycloaddition , triazole , combinatorial chemistry , click chemistry , 1,2,3 triazole , catalysis , medicinal chemistry , organic chemistry
Organocatalytic [3+2] 1,3‐dipolar cycloaddition reactions of β‐keto amides with azides catalyzed by 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) have been developed. This strategy generates 1,4,5‐trisubstituted 1,2,3‐triazole‐4‐carboxamides in high yields and regioselectivities at room temperature. The reaction conditions have been optimized, and the scope of the β‐keto amide and azide have been investigated. A mechanism for the reaction is also proposed.