An efficient metal-free strategy for the synthesis of pharmaceutically relevant benzo[α]carbazoles from the derivatives of readily available 2-phenylindole and bio-renewable acetol in an aqueous biphasic system was d...An efficient metal-free strategy for the synthesis of pharmaceutically relevant benzo[α]carbazoles from the derivatives of readily available 2-phenylindole and bio-renewable acetol in an aqueous biphasic system was developed. This protocol employed a sulfone-containing Bronsted acidic ionic liquid as the catalyst, which could be used for five times without a noticeable decrease in its activity and selectivity. Various substituted 2-phenylindoles and α-hydroxyketones participated in the reaction smoothly, with water as the sole byproduct. Mechanistically, the reaction involved the conventional carbon-nucleophile-induced Heyns-type rearrangement and downstream intramolecular olefination.展开更多
A series of E and Z-isomers of 3-（4＇-substituted benzylidene）-indolin-2-one derivatives were synthesized and separated. Based on their 1H NMR characterization, an unusual counterintuitive deshielding phenomenon for...A series of E and Z-isomers of 3-（4＇-substituted benzylidene）-indolin-2-one derivatives were synthesized and separated. Based on their 1H NMR characterization, an unusual counterintuitive deshielding phenomenon for the protons presenting in the shielding zone of phenyl ring was observed and analyzed for the first time.展开更多
基金supported by the National Natural Science Foundation of China(21761132014,21872060)the Fundamental Research Funds for the Central Universities of China(2016YXZD033)+1 种基金the Fundamental Research Funds for the Central Universities(2019kfyXJJS072)Opening fund of Hubei Key Laboratory of Material Chemistry and Service Failure(2017MCF01K)~~
文摘An efficient metal-free strategy for the synthesis of pharmaceutically relevant benzo[α]carbazoles from the derivatives of readily available 2-phenylindole and bio-renewable acetol in an aqueous biphasic system was developed. This protocol employed a sulfone-containing Bronsted acidic ionic liquid as the catalyst, which could be used for five times without a noticeable decrease in its activity and selectivity. Various substituted 2-phenylindoles and α-hydroxyketones participated in the reaction smoothly, with water as the sole byproduct. Mechanistically, the reaction involved the conventional carbon-nucleophile-induced Heyns-type rearrangement and downstream intramolecular olefination.
基金National Natural Science Foundation of China(Grant No.21172008 and 21372015)
文摘A series of E and Z-isomers of 3-（4＇-substituted benzylidene）-indolin-2-one derivatives were synthesized and separated. Based on their 1H NMR characterization, an unusual counterintuitive deshielding phenomenon for the protons presenting in the shielding zone of phenyl ring was observed and analyzed for the first time.
