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N-Bromosuccinimide mediated synthesis of triazatruxenes from indoles☆

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Abstract A new synthetic method for triazatruxenes from indoles is developed using N-bromosuccinimide (NBS) as a user-friendly reagent. Major reaction parameters including the amount of NBS, substrate concentration, temperature, addition… Click to show full abstract

Abstract A new synthetic method for triazatruxenes from indoles is developed using N-bromosuccinimide (NBS) as a user-friendly reagent. Major reaction parameters including the amount of NBS, substrate concentration, temperature, addition rate and addition method are investigated. Additional experiments are also conducted in order to gain access toward the reaction mechanism. Compared to the use of Br2 in the conventional method, this reaction requires less reaction time, provides better yields, and displays excellent reproducibility. The reaction can be conveniently performed at 10 g scale and it is also applicable to several substituted indoles, benzoindole, and N-alkyl indoles.

Keywords: method; mediated synthesis; synthesis triazatruxenes; bromosuccinimide mediated; reaction; triazatruxenes indoles

Journal Title: Tetrahedron Letters
Year Published: 2017

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