Silver-catalysed double decarboxylative addition-cyclisation-elimination cascade sequence for the synthesis of quinolin-2-ones

An atom-efficient silver-catalysed double carboxylative strategy for the one-step synthesis of quinolin-2-ones via an addition-cyclisation-elimination cascade sequence of oxamic acids to acrylic acids, mediated either thermally or photochemically, is reported. The reaction was applicable to the synt...

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Veröffentlicht in:Organic & biomolecular chemistry 2022-05, Vol.2 (17), p.3469-3474
Hauptverfasser: Mazodze, C. Munashe, Petersen, Wade F
Format: Artikel
Sprache:eng
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Zusammenfassung:An atom-efficient silver-catalysed double carboxylative strategy for the one-step synthesis of quinolin-2-ones via an addition-cyclisation-elimination cascade sequence of oxamic acids to acrylic acids, mediated either thermally or photochemically, is reported. The reaction was applicable to the synthesis of a broad range of quinolin-2-ones and featured a double-disconnection approach that constructed the quinolin-2-one core via the formal and direct addition of a C(sp 2 )-H/C(sp 2 )-H olefin moiety to a phenylformamide precursor. Thermal and photochemical silver-catalysed cascade sequence for the synthesis of quinolin-2-ones is reported. The reaction features two radical decarboxylations and proceeds via the formal addition of an olefin moiety to a phenylformamide precursor.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00521b