- Carbamoyl Radicals via Photoredox Decarboxylation of Oxamic Acids in Aqueous Media: Access to 3,4-Dihydroquinolin-2(1 H)-ones
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The first visible-light-mediated photoredox oxidative approach for generating carbamoyl radicals from oxamic acids is disclosed. Reaction of the generated carbamoyl radicals with electron-deficient alkenes opens efficient access to 3,4-dihydroquinolin-2(1H)-ones under mild conditions through a sequence of intermolecular radical addition, cyclization, and aromatization. The process is compatible with a variety of oxamic acids and electron-deficient alkenes, and a wide variety of 3,4-dihydroquinolin-2(1H)-ones were prepared.
- Bai, Qi-Fan,Jin, Chengan,He, Jing-Yao,Feng, Gaofeng
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- Synthetic method of quinolinone compounds
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The invention discloses a synthetic method of quinolinone compounds. The synthetic method is characterized by comprising the following steps: taking aniline and oxalyl chloride as raw materials, carrying out stirring in an organic solvent, sequentially ad
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- N,N-DISUBSTITUTED LITHIUM BIS(CARBAMOYL)CUPRATE. A CONVENIENT COMPLEX FOR ONE-POT CONVERSIONS OF AMINES TO FORMAMIDES, OXAMIDES, CARBAMATES, AND OXAMIC ACIDS
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Lithium bis(carbamoyl)cuprates (2) were readily derived from secondary amines such as N-methylaniline, N-methylbenzylamine, and diethylamine, under mild carbonylation conditions (0 deg C, 1 atm of carbon monoxide), but diphenylamine and benzylphenylamine were unsuitable as the starting materials.The carbamoylcopper complexes 2 formed in ether were readily converted to the corresponding formamides, oxamides, carbamates, and oxamic acids by the appropriate treatment.The formation and stability of 2 depended much on the solvent used.The higher polarity effect of the solvent (DME, THF, and HMPA) made 2 less stable and caused concomitant evolution of carbon monoxide in further reactions.A palladium catalyst was found to be effective for cross-coupling reactions of 2 with iodobenzene or (E)-β-bromostyrene.
- Wakita, Yoshiaki,Noma, Shun-Ya,Maeda, Minoru,Kojima, Masaharu
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p. 379 - 390
(2007/10/02)
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