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

Molecules

Carlos Espinoza-Hicks²  Rafael Bautista¹  Saúl Frias-Puente²  Vanessa Pelayo²  Eder I. Martínez-Mora²  Francisco Delgado²  Joaquín Tamariz¹ 

[1] Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico

关键词: diacetyl;    p-iminobenzoquinones;    p-diiminobenzoquinones;    N;    N′-dialkyl-1;    4-diaminobenzenes;    diarylamines;   

DOI  :  10.3390/molecules201119716

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.