Condensation of diacetyl with alkyl amines: Synthesis and reactivity of p-iminobenzoquinones and p-diiminobenzoquinones

Carlos Espinoza-Hicks; Rafael Bautista; Saúl Frias-Puente; Vanessa Pelayo; Eder I. Martínez-Mora; Francisco Delgado; Joaquín Tamariz

doi:10.3390/molecules201119716

Condensation of diacetyl with alkyl amines: Synthesis and reactivity of p-iminobenzoquinones and p-diiminobenzoquinones

Carlos Espinoza-Hicks, Rafael Bautista, Saúl Frias-Puente, Vanessa Pelayo, Eder I. Martínez-Mora, Francisco Delgado, Joaquín Tamariz

Escuela Nacional de Ciencias Biológicas (ENCB)

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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.

Original language	English
Pages (from-to)	20719-20740
Number of pages	22
Journal	Molecules
Volume	20
Issue number	11
DOIs	https://doi.org/10.3390/molecules201119716
State	Published - 20 Nov 2015

Keywords

Diacetyl
Diarylamines
N,N′-dialkyl-1,4-diaminobenzenes
P-diiminobenzoquinones
P-iminobenzoquinones

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10.3390/molecules201119716

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@article{05d4f512e37c47a8abf9120b9965adba,

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.",

keywords = "Diacetyl, Diarylamines, N,N′-dialkyl-1,4-diaminobenzenes, P-diiminobenzoquinones, P-iminobenzoquinones",

author = "Carlos Espinoza-Hicks and Rafael Bautista and Sa{\'u}l Frias-Puente and Vanessa Pelayo and Mart{\'i}nez-Mora, {Eder I.} and Francisco Delgado and Joaqu{\'i}n Tamariz",

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year = "2015",

month = nov,

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doi = "10.3390/molecules201119716",

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TY - JOUR

T1 - Condensation of diacetyl with alkyl amines

T2 - Synthesis and reactivity of p-iminobenzoquinones and p-diiminobenzoquinones

AU - Espinoza-Hicks, Carlos

AU - Bautista, Rafael

AU - Frias-Puente, Saúl

AU - Pelayo, Vanessa

AU - Martínez-Mora, Eder I.

AU - Delgado, Francisco

AU - Tamariz, Joaquín

PY - 2015/11/20

Y1 - 2015/11/20

N2 - 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.

AB - 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.

KW - Diacetyl

KW - Diarylamines

KW - N,N′-dialkyl-1,4-diaminobenzenes

KW - P-diiminobenzoquinones

KW - P-iminobenzoquinones

UR - http://www.scopus.com/inward/record.url?scp=84949980159&partnerID=8YFLogxK

U2 - 10.3390/molecules201119716

DO - 10.3390/molecules201119716

M3 - Artículo

C2 - 26610447

SN - 1420-3049

VL - 20

SP - 20719

EP - 20740

JO - Molecules

JF - Molecules

IS - 11

ER -

Condensation of diacetyl with alkyl amines: Synthesis and reactivity of p-iminobenzoquinones and p-diiminobenzoquinones

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