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

Autor:	Yu. V. Kharchenko, Irina V. Omelchenko, I. M. Gella, Oleg V. Shishkin, Valeriy D. Orlov
Rok vydání:	2012
Předmět:	Dimethyl acetylenedicarboxylate chemistry.chemical_compound chemistry Nucleophile Stereochemistry Organic Chemistry Pyridine Imidazole Imidazoline receptor Ketene Imide Medicinal chemistry Acetophenone
Zdroj:	Chemistry of Heterocyclic Compounds. 48:1204-1212
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-012-1123-y
Popis:	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.
Databáze:	OpenAIRE
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