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Studies on isocyanides and related compounds. A convenient synthesis of 2,3‐disubstituted spiroimidazolones
Author(s) -
Bossio Ricardo,
Marcaccini Stefano,
Papaleo Sandro,
Pepino Roberto
Publication year - 1994
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.5570310225
Subject(s) - chemistry , formamides , carbanion , isocyanide , butyllithium , ammonium formate , organic chemistry , condensation , ammonium , acetamide , medicinal chemistry , acetonitrile , formamide , physics , thermodynamics
The four‐component condensation between cycloketones 1 , ammonium formate, and isocyanides 2 afforded formamides 3 , which were dehydrated to the corresponding isocyanides 4 . Upon treatment with n ‐butyllithium, compounds 4 cyclized to spiroimidazolones 6 , via the carbanions 5 . A series of 2,3‐disubstituted spiroimidazolones 8 was obtained by reacting 5 with aldehydes 7 .