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Synthesis of 3,5,5‐Trisubstituted 4‐Hydroxy‐4 H ,5 H ‐1,2,4‐oxadiazoles through the Condensation of N ‐Hydroxyamidoximes and Ketones or Aldehydes
Author(s) -
Liu Ning,
Zhai LianJie,
Lian Peng,
Li Hui,
Wang BoZhou
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.201500083
Subject(s) - chemistry , methanol , condensation , catalysis , condensation reaction , reaction conditions , single crystal , organic chemistry , combinatorial chemistry , medicinal chemistry , crystallography , physics , thermodynamics
An interesting class of heterocyclic compounds, 1,2,4‐oxadiazoles and their derivatives have attracted the attention of chemists because of their use in the development of new pharmaceuticals and functional materials. Herein, a catalyst‐free reaction of N ‐hydroxyamidoxime with various ketones or aldehydes has been investigated. The reaction was carried out in methanol under mild conditions and gave 3,5,5‐trisubstituted 4‐hydroxy‐4 H ,5 H ‐1,2,4‐oxadiazole derivatives in excellent yields. The structure of product 3f was confirmed by single‐crystal X‐ray diffraction studies.