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Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
J. Mex. Chem. Soc vol.55 no.4 Ciudad de México oct./dic. 2011
Article
Preparation and Some Reactions with 3(Quinolin3yl)3Oxopropanoic Acid
Mohamed Abass,1* Elhossain A. Mohamed,1 Mostafa M. Ismail,1 and Aisha S. Mayas2
1 Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Postal Code 11757, Cairo, Egypt. Tel.: +201093694622. m.abass@chemist.com
2 Department of Chemistry, Faculty of Education, Sana University, Sana, Yemen.
Received May 10, 2011.
Accepted August 25, 2011.
Abstract
Preparation of quinolinyl3oxopropanoic acid 2 was accomplished by hydrolysis of pyranoquinolinedione 1 in aqueous alkaline medium. The chemical behavior of this βketo acid 2 towards nitrosation, coupling with a diazonium salt, esterification, condensation with 2,2dimethoxyethanamine, hydrazinolysis, Knoevenagel condensation with isatine, salisyaldehyde, 3formylquinolones, and 3formylchromone, was investigated. Also many of the products of these reactions were found obtainable using either pyranoquinolinedione 1 or βketo acid 2, under the same conditions.
Key words: Quinolin2(1H)one, βKetocarboxylic acid, Pyrano[3,2c]quinoline, Knoevenagel condensation, heterocyclization reactions.
Resumen
La preparación del ácido quinolinil3oxopropanoico 2 se realizó por hidrólisis de la piranoquinolindiona 1 en medio acuoso alcalino. Se investigó el comportamiento químico de este βcetoácido 2 en reacciones de nitrosación, acoplamiento con sales de diazonio, esterificación, condensación con 2,2dimethoxyethanamine, hidrazinólisis, condensación de Knoevenagel con isatina, salicilaldehido, 3formilquinolones y 3formilchromonas. Muchos de los productos de estas reacciones pueden obtenerse mediante el uso ya sea de la piranoquinolindiona 1 o del βcetoácido 2, bajo las mismas condiciones.
Palabras clave: Quinolin2(1H)ona, ácido βcetocarboxílico, pirano [3,2c] quinolina, condensación de Knoevenagel, reacciones de heterociclización.
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