An Efficient New Route for the Synthesis of Some 3‐Hterocyclylquinolinones via Novel 3‐(1, 2‐Dihydro‐4‐hydroxy‐1‐methyl‐2‐oxoquinolin‐3‐yl)‐3‐oxopropanal and Their Antioxidant Screening. (31st August 2017)

• Record Type: Journal Article
• Authors: Hassan, Mohamed M.; Hassanin, Hany M.
• Is Part Of: Journal of heterocyclic chemistry. Volume 54:Number 6(2017:Nov.)
• Page Start: 3321
• Page End: 3330
• Publication Date: 2017-08-31
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2952
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : 3‐(4‐hydroxy‐1‐methylquinoline‐3‐yl)‐3‐oxoproponal (5 ) was synthesized from 3‐[(E)‐3‐(dimethylamino)‐2‐propenoyl]‐4‐hydroxy‐1‐methyl‐2(1 H )‐quinolinone (3 ) and was utilized as a starting precursor material. A convenient new route to functionalized 3‐heterocyclyl 4‐hydroxy‐2(1 H )‐quinolinones such as pyrazolyl, isoxazolyl, pyrimidinyl, azepineyl, pyridonyl, and pyranyl heterocycles was described via cyclization of compound5 with some N and C ‐nucleophiles. The newly synthesized aldehyde5 showed only one ring closure possibility with maximum yield instead of using compound3 that exhibited different regioselective ring closure routes with minimum yields. All newly synthesized products were structurally elucidated on the basis of their relevant spectroscopic data and elemental microanalyses. The antioxidant activity of the products was screened in a series of in vitro tests. Abstract :