ChemInform Abstract: Synthetic Approach for Constructing the 1‐Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids.

Bautista, Rafael; Jerezano, Alberto V.; Tamariz, Joaquı́n

doi:10.1002/chin.201306071

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2015

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“…Diarylamines have become important synthetic targets as fine chemicals and precursors of a variety of N -containing pharmacological and natural products [38,39,40], such as carbazoles and ellipticines [41,42,43,44,45]. Due to the importance of diarylamines, a great number of synthetic approaches have been designed for their preparation [46,47,48].…”

Section: Resultsmentioning

confidence: 99%

Condensation of Diacetyl with Alkyl Amines: Synthesis and Reactivity of p-Iminobenzoquinones and p-Diiminobenzoquinones

et al. 2015

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Condensation reactions between diacetyl and α-branched primary alkylamines under mild and neutral conditions provided a mixture of 2,5-dimethylbenzoquinone(alkylimines), 2,5-dimethylbenzoquinone(bis-alkyldiimines), and N,N 1 -dialkyl-2,5-dimethylbenzene-1,4-diamines, which were efficiently separated as pure products by column chromatography. Both 2,5-dimethylbenzoquinone(alkylimines) and 2,5-dimethylbenzoquinone(bis-alkyldiimines) underwent an interchange of the alkylimino group when treated with anilines, followed by reductive aromatization, to provide diarylamines and 1,4-dianilinobenzenes, respectively. Evaluation was also made of the reactivity and selectivity of these compounds in the presence of anilines, thiophenols and alkylhalides.

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