Studies on Quinolin-2(1H)-One Derivatives: Synthetic Access to Pyrano[3,2-c] Quinoline and 3-Substituted Quinoline Derivatives
Fathy M. A.El-Taweel *
Department of Chemistry, Faculty of Science, 34517, New Damietta City, Damietta University, Egypt
Abdel- Ghani A. Elagamey
Department of Chemistry, Faculty of Science, 34517, New Damietta City, Damietta University, Egypt
Muhammad H. M. Khalil
Department of Chemistry, Faculty of Science, 34517, New Damietta City, Damietta University, Egypt
*Author to whom correspondence should be addressed.
Abstract
4H-pyrano[3,2-c]quinoline derivatives 6a-f were prepared via reacting arylmethylenemalononitriles 2-c,g with 4-hydroxyquinolines 1a-c or 1e,f. Refluxing 6d with formic acid or acetic anhydride gave 7-(2-chlorophenyl)-5-methyl-5H-pyrimido [5'4':5,6]pyrano[3,2-c]quinoloine-6,8-(7H,11H)-dione 7 and 7-(2-chlorophenyl)-5,10-dimethyl-5H-pyrimido [5'4':5,6] pyrano[3,2-c] quinoloine-6,8-(7H,9H)-dione 9 respectively.Reacting 1d with 2a,d gave pyrano[2,3-b] pyridine12a,b.Compounds 1c or 1g reacted with 2e,f to give 11-amino-8-oxo-9-substituted -5,6,8,9-tetrahydro-4H-pyrano[3,2-c]pyrido[3,2,1-ij]quinoline-10-carbonitriles 15a,b. Reacting 1c or 1g with ethoxymethylenemalononitrile 16 afforded 11-imino-4H,5H,6H,9H-benzo[ij][2,3-b]quinolizin-8-one 18. Also, reacting 1c or 1g with methyl 2-benzolyamino-3-dimethylaminopropionate 19 yield N-(6-(1-hydroxy-3-oxo-3,5,6,7-tetrahydropyrido[3,2,1-ij]quinolin-2-yl)-2-oxo-2H-pyran-3-yl)benzamide 21 and N-(8,11-dioxo-5,6,8,11-tetrahydro-4H-pyrano[3,2-c]pyrido[3,2,1-ij]quinolin-10-yl)benzamide 22 respectively. Condensation of 1c with aromatic aldehydes afford 2,2'-(arylmethylene)bis(1-hydroxy-6,7-dihydropyrido[3,2,1-ij]quinolin-3(5H)-ones) 28a-d.
Keywords: Arylmethylenemalononitriles, 4-hydroxyquinolines, 4H-pyrano[3,2-c] quinoline