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Heterocycles from substituted amides, V. . 1,2,3,5‐Oxathiadiazolin‐4‐one 2‐oxides from thionyl chloride and N ‐hydroxyureas
Author(s) -
Chupp John P.,
Dahm Donald J.,
Leschinsky Kindrick L.
Publication year - 1975
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.5570120308
Subject(s) - thionyl chloride , chemistry , ring (chemistry) , aryl , chloride , alkyl , medicinal chemistry , nitrogen , group (periodic table) , organic chemistry
The reaction of certain N ‐hydroxy‐ N ‐methyl‐ N ′‐aryl ureas, 2 , with thionyl chloride are shown to give a new heterocycle, 1,2,3,5‐oxathiadiazolin‐4‐one 2‐oxides, 3 , in a synthesis that appears to have more severe structural requirements than the previously reported ring closures from α‐hydroxyacylanilides and thionyl chloride. Isolable amounts of 3 are obtained only if the aryl group contains deactivating substituents, and the hydroxy group is attached to the N ‐alkyl nitrogen; otherwise, resin formation or ring chlorination are found to occur. The assigned structure as 3 was verified by a full three dimensional X‐ray analysis of a representative example, 3a , 3‐(4‐bromophenyl)‐5‐methyl‐1,2,3,5‐oxathiadiazolin‐4‐one.