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
N1 - Publisher Copyright:
© 2015 by The Authors.
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 -