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Chemical reactions of cycloalkanespirohydantoins. Part 3 . Acid‐catalyzed reaction of 4‐hydroxy‐2‐imidazolidinones. Preparation of bis(1,3‐diaza‐2‐oxospiro[4,5]decyl‐4) ether
Author(s) -
Pedregal Carmen,
Espada Modesta,
Salazar Loreto,
Elguero José
Publication year - 1986
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.5570230235
Subject(s) - chemistry , trifluoroacetic anhydride , trifluoroacetic acid , ether , catalysis , organic chemistry , reaction conditions , medicinal chemistry
The use of N ‐carbamoyliminium ion initiated reactions for the generation of spiroimidazolidin‐2‐ones has been successfully exploited. N 3 ‐Substituted‐4‐hydroxy‐2‐imidazolidinones have been treated under acid conditions to give the rearranged imidazolinones. Only in the case of N 3 ‐dialkylaminomethyl‐4‐hydroxy‐5‐cyclohexanespiro‐2‐imidazolidinones upon treatment with trifluoroacetic anhydride/trifluoroacetic acid afforded a mixture containing bis(1,3‐diaza‐2‐oxospiro[4,5]decyl‐4) ether with the rearranged imidazolidinone.