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

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...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2012-11, Vol.48 (8), p.1204-1212
Main Authors: Orlov, V. D., Kharchenko, Yu. V., Gella, I. M., Omel’chenko, I. V., Shishkin, O. V.
Format: Article
Language:English
Subjects:
Alkaloids
Chemical tests and reagents
Chemistry
Chemistry and Materials Science
Nitrogen
Olefins
Organic Chemistry
Pharmacy
Pyridine
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-012-1123-y