Condensation of Diacetyl with Alkyl Amines: Synthesis and Reactivity of p-Iminobenzoquinones and p-Diiminobenzoquinones
Autor: | Rafael Bautista, Vanessa Pelayo, Saúl Frias-Puente, Joaquín Tamariz, Carlos Espinoza-Hicks, Francisco Delgado, Eder I. Martínez-Mora |
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Jazyk: | angličtina |
Rok vydání: | 2015 |
Předmět: |
N
N′-dialkyl-1 4-diaminobenzenes Molecular Conformation Pharmaceutical Science diarylamines Chemistry Techniques Synthetic Article Analytical Chemistry diacetyl lcsh:QD241-441 chemistry.chemical_compound Column chromatography lcsh:Organic chemistry Drug Discovery Benzoquinones Organic chemistry p-iminobenzoquinones p-diiminobenzoquinones Reactivity (chemistry) Physical and Theoretical Chemistry Amines Alkyl chemistry.chemical_classification Organic Chemistry Condensation Aromatization Condensation reaction Diacetyl chemistry Chemistry (miscellaneous) Molecular Medicine Selectivity |
Zdroj: | Molecules, Vol 20, Iss 11, Pp 20719-20740 (2015) Molecules Volume 20 Issue 11 Pages 20719-20740 Molecules; Volume 20; Issue 11; Pages: 20719-20740 |
ISSN: | 1420-3049 |
Popis: | 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. |
Databáze: | OpenAIRE |
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