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1,3‐Dipolar Cycloaddition of Imidazole Derivatives with Nitrile Oxide: Synthesis of Imidazo[1,2,4]oxadiazole Derivatives
Author(s) -
Jiang KunMing,
Zhang JianQiang,
Jin Yi,
Lin Jun
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700347
Subject(s) - chemistry , imidazole , nitrile , cycloaddition , oxadiazole , tricyclic , 1,3 dipolar cycloaddition , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , catalysis
Abstract A concise and efficient synthesis of imidazo[1,2,4]oxadiazole derivatives that proceeds through the [3+2] cycloaddition of 2‐chloro‐1 H ‐benzo[ d ]imidazole with nitrile oxides has been developed. This strategy can conveniently construct tricyclic imidazole heterocyclic derivatives that contain a broad range of functional groups. Compound 3 p showed excellent cytotoxic activity against the KYSE410 cell line (IC 50 =0.26 μ m ). These tricyclic imidazole heterocyclic derivatives are promising candidates for drug discovery.