- Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones
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A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.
- Wang, Guanjie,Hu, Wanyao,Hu, Zhouli,Zhang, Yuxia,Yao, Wei,Li, Lin,Fu, Zhenqian,Huang, Wei
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p. 3302 - 3307
(2018/07/29)
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- Visible-Light-Mediated Aerobic Oxidation of N-Alkylpyridinium Salts under Organic Photocatalysis
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Quinolones and isoquinolones exhibit diverse biological and pharmaceutical activities, and their synthesis is highly desirable under mild conditions. Here, a highly efficient and environmentally friendly visible light-mediated aerobic oxidation of readily available N-alkylpyridinium salts has been developed with Eosin Y as the organic photocatalyst and air as the terminal oxidant, and the reaction provided quinolones and isoquinolones in good yields. The method shows numerous advantages including mild and environmentally friendly conditions, high efficiency, tolerance of wide functional groups and low cost. Furthermore, 4-desoxylonimide with important pharmaceutical activities was effectively prepared by using our method. Therefore, the present method should provide a novel and useful strategy for synthesis and modification of N-heterocycles.
- Jin, Yunhe,Ou, Lunyu,Yang, Haijun,Fu, Hua
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supporting information
p. 14237 - 14243
(2017/10/17)
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- On the Reaction of Some 2H-Pyran-2-one Derivatives with Primary Amines
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The versatile reactivity of 6-unsubstituted 2H-pyran-2-ones towards aliphatic and aromatic amines has been studied.It was found that the result of the reaction depends not only on the substitution of 2H-pyran-2-ones and on the structure of amines, but also on the stoichiometric ratio of reacting compounds.
- Kvita, Vratislav,Sauter, Hanspeter,Rihs, Grety
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p. 407 - 416
(2007/10/02)
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