title: Condensation of Diacetyl with Alkyl Amines: Synthesis and Reactivity of p-Iminobenzoquinones and p-Diiminobenzoquinones.
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.
authors.affiliation: Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico. hick_1107@hotmail.com.
authors.forename: Carlos
authors.initials: C
authors.lastname: Espinoza-Hicks
authors.affiliation: Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico. jimbe31@hotmail.com.
authors.forename: Rafael
authors.initials: R
authors.lastname: Bautista
authors.affiliation: Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico. eleanor_500m@hotmail.com.
authors.forename: Saúl
authors.initials: S
authors.lastname: Frias-Puente
authors.affiliation: Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico. fiosara29@gmail.com.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Pelayo
authors.affiliation: Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico. eder.qfb@gmail.com.
authors.forename: Eder I
authors.initials: EI
authors.lastname: Martínez-Mora
authors.affiliation: Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico. jfdelgador@gmail.com.
authors.forename: Francisco
authors.initials: F
authors.lastname: Delgado
authors.affiliation: Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala, 11340 México, Mexico. jtamarizm@gmail.com.
authors.forename: Joaquín
authors.initials: J
authors.lastname: Tamariz
mesh_terms: D000588:Amines / Q000737:chemistry*; D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003931:Diacetyl / Q000737:chemistry*; D008968:Molecular Conformation
chemical_list: D000588:Amines; D016227:Benzoquinones; D003931:Diacetyl
keywords: N,N′-dialkyl-1,4-diaminobenzenes; diacetyl; diarylamines; p-diiminobenzoquinones; p-iminobenzoquinones