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- Title
Synthesis of certain novel 4H-pyrano[3,2-h]quinoline derivatives.
- Authors
El-Agrody, Ahmed M.; Al-Ghamdi, Abdullah M.
- Abstract
Treatment of 8-hydroxyquinoline 1a and 8-hydroxy-2-methylquinoline 1b with a-cyano-p-chloro/bromocinnamonitriles 2a,b provided 4H-pyrano[3,2-h]quinoline-3-carbonitrile derivati-ves 3a-d, while treatment of (E) 2-(4-chlorostyryl)-8-hydroxyquinoline 7 with a-cyano-p-chloro/bromocinnamonitriles 2a,b and ethyl a-cyano-p-chloro/bromocinnamates 2d,e provided 4H-pyrano[3,2-h]quinoline-3-carbonitrile derivatives 8a,b and ethyl 4H-pyrano[3,2-h]quinoline-3-carboxylate derivatives 9a,b respectively. Interaction of 8-hydroxyquinoline 1a and 8-hydroxy-2-methylquinoline 1b with a-cyano-p-fluorocinnamonitrile 2c afforded 2-[4-(piperidin-1-yl)benzylidene]malononitrile 5 via a nucleophilic aromatic substitution reaction. The reactivity of 2-hydroxyquinoline and its 2-substituted derivatives towards a-cyano-p-chloro/bromo-cinnamonitriles and ethyl a-cyano-p-chloro/bromocinnamates are discussed in this work. Structures of these compounds were established on the basis of IR, 1H NMR, 13C NMR, 13C NMR-DEPT and MS data.
- Subjects
AROMATIC compound synthesis; QUINOLINE derivatives; HYDROXYQUINOLINE; CARBONITRILES; CHEMICAL structure; CARBOXYLATE derivatives
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2011, p134
- ISSN
1551-7004
- Publication type
Article