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- Title
Reactions of ketene aminals with n-arylmaleimides and dimethyl acetylenedicarboxylate, a direct pathway to derivatives of pyrrolo[1,2- a]imidazole and imidazo[1,2- a]pyridine.
- Authors
Orlov, V.; Kharchenko, Yu.; Gella, I.; Omel'chenko, I.; Shishkin, O.
- Abstract
The addition of N-arylmaleimides or dimethyl acetylenedicarboxylate to 2-imidazolideneacetophenones proceeds at the most nucleophilic carbon atom of the acetophenone derivatives and results in a rearrangement to give derivatives of 5-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole or imidazo[1,2-a]pyridine, respectively. In the case of 2-imidazolidenecyclopentanones and 2-imidazolidine-cyclohexanones, the reaction terminates upon the addition of imide or dimethyl acetylenedicarboxylate at the nitrogen atom of the imidazoline system.
- Subjects
KETENES; ETHANES; IMIDAZOLES; PYRIDINE derivatives; ACETOPHENONE derivatives; REARRANGEMENTS (Chemistry)
- Publication
Chemistry of Heterocyclic Compounds, 2012, Vol 48, Issue 8, p1204
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-012-1123-y