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Ring transformations of heterocycles. Part 1 . Transformation of 4‐amino‐Δ 2 ‐1,2,4‐oxadiazolines into 1,3,4‐oxadiazoles
Author(s) -
ElAbadelah M. M.,
Nazer M. Z.,
Hussein A. Q.,
Awadallah A. M.,
Rademacher P.,
Woydt M.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280513
Subject(s) - chemistry , ring (chemistry) , chloroacetic acid , toluene , aryl , transformation (genetics) , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , alkyl , gene
3‐Aryl‐4‐amino‐δ 2 ‐1,2,4‐oxadiazolines 3 and their N ‐chloroacetyl derivatives 4 , upon treatment with chloroacetic anhydride in refluxing toluene, afford 2‐chloromethyl‐5‐aryl‐1,3,4‐oxadiazoles 5 , suggesting the conversion sequence 3 → 4 → 5 . The generality of the new ring transformation 4 → 5 is supported similar conversion of other 4‐(acylamino)‐1,2,4‐oxadiazolines 8 to 1,3,4‐oxadiazoles 9 .