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Synthesis of Trisubstituted 1,2,4‐Triazoles from Azlactones and Aryldiazonium Salts by a Cycloaddition/Decarboxylation Cascade
Author(s) -
Yu XiaoYe,
Xiao WenJing,
Chen JiaRong
Publication year - 2019
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.201901467
Subject(s) - cycloaddition , chemistry , decarboxylation , reagent , combinatorial chemistry , aryl , context (archaeology) , organic chemistry , catalysis , paleontology , alkyl , biology
Azlactones, also known as oxazolones, possess multiple reactive sites, and are thus widely used as versatile class of reagents in organic synthesis, particularly in cycloaddition reactions for heterocycle synthesis. However, the use of azlactones as three‐member fragments in cycloaddition reactions/decarboxylation cascade were rarely explored. In this context, a metal‐free cycloaddition/decarboxylation reaction between azlactones and aryldiazonium salts has been achieved for the first time, which provides efficient and facile access to privileged 1,3,5‐trisubstituted 1,2,4‐triazoles. Notably, aryldiazonium salts serve as two‐nitrogen unit rather than the sources of aryl radicals in this transformation, which provides an alternative class of reagents for the construction of N‐heterocycles.