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• W3009528061 startingPage "829" @default.
• W3009528061 abstract "Abstract We report the conversion of 2,3‐dihydrobenzo[ b ][1,4]dioxine‐2‐carboxamides, (derived from 2,3‐dihydrobenzo[ b ][1,4]dioxine‐2‐carboxylic acid and 2‐haloanilines) to 3‐oxoquinolin‐2(1 H )‐one motifs using catalytic amounts of Pd(OAc) 2 , PPh 3, BINOL and Cs 2 CO 3 (1.5 equiv). This conversion occurred via the less common formal 6‐ endo ‐trig cyclization and chelation‐controlled β ‐arylation (Heck‐type reaction) pathways. Initially, a base‐mediated ring‐opening of the 2,3‐dihydrobenzo[ b ][1,4]dioxine moiety generates an acrylamide intermediate in situ, which then undergoes a formal 6‐ endo ‐trig cyclization‐involved Heck‐type reaction to afford 3‐oxoquinolin‐2(1 H )‐one motif. The proposed acrylamide intermediate was isolated, characterized by the X‐ray structure analysis and then, it was also treated under the experimental conditions, which afforded the expected 3‐oxoquinolin‐2(1 H )‐one; thus, providing a strong support for the proposed mechanism. Various 3‐oxoquinolin‐2(1 H )‐one motifs were synthesized in moderate to good yields. Representative 3‐oxoquinolin‐2(1 H )‐one motifs were characterized by X‐ray analysis." @default.
• W3009528061 created "2020-03-13" @default.
• W3009528061 creator A5038086935 @default.
• W3009528061 creator A5061409016 @default.
• W3009528061 creator A5065453343 @default.
• W3009528061 date "2020-03-25" @default.
• W3009528061 modified "2023-09-27" @default.
• W3009528061 title "Conversion of 2,3‐Dihydrobenzo[ <i>b</i> ][1,4]dioxine‐2‐carboxamides to 3‐Oxoquinolin‐2(1 <i>H</i> )‐ones via Ring‐Opening and Formal 6‐ <i>endo</i> ‐trig Cyclization‐Involved Heck Reactions" @default.
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• W3009528061 doi "https://doi.org/10.1002/ajoc.202000096" @default.
• W3009528061 hasPublicationYear "2020" @default.
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