Abstract
4-hydroxyquinolinones 7 were applied as 1,3-dinucleophiles in the reaction with Baylis-Hillman adduct acetates 6 to synthesize, in high yields of 75-92%, novel 2H-pyrano[3,2-c]quinoline-2,5(6H)-diones which are present in a number of biologically active compounds. The reaction was carried out under different conditions to achieve the optimum ones. The results indicated that acetonitrile as solvent and K2CO3 as base, under reflux conditions, were the optimum conditions. The reaction times are short and the experimental procedure is straightforward.
Keywords: 4-hydroxyqouinolone, Baylis–Hilmanadductacetates, pyranoquinolones, tandem reaction
Letters in Organic Chemistry
Title:An Efficient Synthesis of the 2H-pyrano[3,2-c]quinoline-2,5(6H)-dione System via Tandem Reaction of 4-hydroxyquinolinones to Baylis-Hillman Adduct Acetates
Volume: 9 Issue: 10
Author(s): Firouz M. Moghaddam, Behzad K. Foroushani and Elaheh L. Kalahroodi
Affiliation:
Keywords: 4-hydroxyqouinolone, Baylis–Hilmanadductacetates, pyranoquinolones, tandem reaction
Abstract: 4-hydroxyquinolinones 7 were applied as 1,3-dinucleophiles in the reaction with Baylis-Hillman adduct acetates 6 to synthesize, in high yields of 75-92%, novel 2H-pyrano[3,2-c]quinoline-2,5(6H)-diones which are present in a number of biologically active compounds. The reaction was carried out under different conditions to achieve the optimum ones. The results indicated that acetonitrile as solvent and K2CO3 as base, under reflux conditions, were the optimum conditions. The reaction times are short and the experimental procedure is straightforward.
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Cite this article as:
M. Moghaddam Firouz, K. Foroushani Behzad and L. Kalahroodi Elaheh, An Efficient Synthesis of the 2H-pyrano[3,2-c]quinoline-2,5(6H)-dione System via Tandem Reaction of 4-hydroxyquinolinones to Baylis-Hillman Adduct Acetates, Letters in Organic Chemistry 2012; 9 (10) . https://dx.doi.org/10.2174/157017812803901953
DOI https://dx.doi.org/10.2174/157017812803901953 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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