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- W2487432850 abstract "The Engler indole synthesis entails the Lewis acid-promoted reaction of benzoquinone imines with styrenes and enol ethers to give a suite of heterocycles including dihydroindoles and indoles. The Engler indole synthesis is related to the Nenitzescu indolization both in benzoquinone starting materials and 5-hydroxyindole products. Engler and colleagues extended to the reaction of N-phenylsulfonylimino-1,4-benzoquinones with enol ethers derived from 3- and 4-piperidone to give β- and γ-tetrahydrocarbolines. Kita and coworkers described an intermolecular version that resembles the procedure of Engler. This features phenyliodine(III) bis(trifluoroacetate) (PIFA) reaction with N-tosylaniline, followed by nucleophilic attack by an activated olefin, and cyclization to give either N-tosylindoline or N-tosylindole. The Engler-Kita indole synthesis, combined with the Nenitzescu indolization, represent powerful and versatile syntheses of 5-hydroxyindoles." @default.
- W2487432850 created "2016-08-23" @default.
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- W2487432850 date "2016-06-17" @default.
- W2487432850 modified "2023-09-23" @default.
- W2487432850 title "Engler-Kita Indole Synthesis" @default.
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- W2487432850 doi "https://doi.org/10.1002/9781118695692.ch16" @default.
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