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Molecules 2015, 20(11), 20719-20740; doi:10.3390/molecules201119716

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

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico
Present address: Departamento de Investigación y Desarrollo, Signa, S.A. de C.V., Av. Industria Automotriz No. 301, Zona Industrial Toluca, 50200, Toluca, Edo. de México, Mexico.
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Author to whom correspondence should be addressed.
Academic Editor: Roman Dembinski
Received: 16 October 2015 / Revised: 5 November 2015 / Accepted: 6 November 2015 / Published: 20 November 2015
(This article belongs to the Section Organic Synthesis)
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Abstract

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′-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. View Full-Text
Keywords: diacetyl; p-iminobenzoquinones; p-diiminobenzoquinones; N,N′-dialkyl-1,4-diaminobenzenes; diarylamines diacetyl; p-iminobenzoquinones; p-diiminobenzoquinones; N,N′-dialkyl-1,4-diaminobenzenes; diarylamines
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Espinoza-Hicks, C.; Bautista, R.; Frias-Puente, S.; Pelayo, V.; Martínez-Mora, E.I.; Delgado, F.; Tamariz, J. Condensation of Diacetyl with Alkyl Amines: Synthesis and Reactivity of p-Iminobenzoquinones and p-Diiminobenzoquinones. Molecules 2015, 20, 20719-20740.

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