Studies on 2(1H)-Quinolone Derivatives: Synthetic Access to Pyrano[3,2-c] Quinoline and 3-Substituted Quinoline Derivatives

Elagamey, A A; El-Taweel, F.; Khalil, M H.M

doi:10.21608/sjdfs.2012.194258

Studies on 2(1H)-Quinolone Derivatives: Synthetic Access to Pyrano[3,2-c] Quinoline and 3-Substituted Quinoline Derivatives

Document Type : Original articles

Authors

Department of Chemistry, Faculty of Science, New Damietta City, Damietta University, Egypt

10.21608/sjdfs.2012.194258

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 give 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] quinoline-6,8-(7H,9H)-dione 9 respectively. Reacting 1d with 2a,d give pyrano[2,3-b] pyridine 12a,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 afford 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.

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