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Cyclic transformations of 5‐aryl(or benzyl)‐3‐(2‐bromoethyl‐ 1,3,4‐oxadiazol‐2(3 H )‐ones into 1‐aminoimidazolidin‐2‐one and 5,6‐dihydro‐4 H ‐1,3,4‐oxadiazine derivatives
Author(s) -
Milcent René,
Barbier Géo
Publication year - 1992
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.5570290508
Subject(s) - chemistry , aryl , transformation (genetics) , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , alkyl , gene
5‐Aryl(or benzyl)‐3‐(2‐bromoethyl)‐1,3,4‐oxadiazol‐2(3 H )‐ones 3 have been prepared. They were reacted with secondary alkylamines without any change of the heterocycle to give amino derivatives 6 , but with primary alkylamines, cyclic transformation occurred to give 1‐acylamino‐3‐alkylimidazolidin‐2‐ones 7 . In the presence of sodium alcoholate, bromo compounds 3 were transformed into 2‐aryl(or benzyl)‐4‐alkoxycarbonyl‐5,6‐dihydro‐4 H ‐1,3,4‐oxadiazines 9 .