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- Title
Heterocyclic ketones in the pfitzinger reaction.
- Authors
Moskalenko, A. I.; Boeva, A. V.; Boev, V. I.
- Abstract
By the reaction of isatin with heterocyclic ketones ( N- tert-butoxycarbonyl derivatives of pyrrolidin-3-one, piperidin-4-one, piperidin-3-one, 1,2,3,4-tetrahydroquinolin-4-one, 8-azabicyclo[3.2.1]octan-3-one, tetrahydropyran-4-one, tetrahydrobenzopyran-4-one) in the presence of KOH (the Pfitzinger reaction) were synthesized quinoline-4-carboxylic acids [4,3]fused with the respective heterocycles. These acids were involved in the reactions with diazomethane and amines at the carboxy group leading to methyl esters and amides, respectively. The esters obtained reacted with hydrazine hydrate affording the acid hydrazides, which entered in the condensation with benzaldehyde to form phenylhydrazones. The esters and amides containing N-tert-butoxycarbonyl fragment lost the tert-butoxycarbonyl group easily to form the secondary amines dihydrochlorides, the [4,3]fused quinoline-4-carboxylic acid derivatives.
- Subjects
KETONIC acids; ORGANIC compounds; HYDROGEN; CARBOXYLIC acids; HETEROCYCLIC compounds; DIAZOMETHANE
- Publication
Russian Journal of General Chemistry, 2011, Vol 81, Issue 2, p397
- ISSN
1070-3632
- Publication type
Article
- DOI
10.1134/S1070363211020198