Abstract
The significance of the acylation reaction of amines is presented in the literary reference information. The products of the reaction of the corresponding amides are important intermediates in obtaining practically useful compounds. It has been shown that the most common methods of acylfunctionalization of amines are acetylation, trifluoroacetylation and formylation, usually acid anhydrides or chlorides are used as acylating reagents in these reactions in the presence of highly toxic and expensive catalysts. The authors have developed an approach to the synthesis of a number of N-acylated amino-9,10-anthraquinones, which is based on the use of a new acylation system consisting of a strong organic acid and ammonium thiocyanate. It has been determined that 1-amino-9,10-anthraquinone and its derivatives in the presence of the two-fold excess of ammonium thiocyanate can be acetylated only by formic and trifluoroacetic acids. 2-Amino-9,10-anthraquinone additionally can be acetylated by mercaptoacetic and acetic acids. The scheme of the reaction discovered has been proposed, it involves in situ generation of ammonium acetate from carboxylic acid and ammonium thiocyanate, which serves as the acylating reagent.
Highlights
Table continued2l in work [26] on direct acetylation of anilines with ammonium acetate in acetic acid, as well as the experimental data on the absence of reactions when instead of thiocyanate ammonium, thiocyanate potassium or ammonium chloride were used, and direct conversion of 2-amino-9,10-anthraquinone 1e to amide 2h in the reaction with the excess of ammonium acetate in acetic acid
N-АЦИЛЮВАННЯ АМІНО-9,10-АНТРАХІНОНІВ СИСТЕМОЮ СИЛЬНА КАРБОНОВА КИСЛОТА – ТІОЦІАНАТ АМОНІЮ В.I.Зварич, M.В.Стасевич, В.В.Лунін, В.П.Новіков, M.В.Вовк Ключові слова: аміно-9,10-антрахінони; карбонові кислоти; тіоціанат амонію; ацетат амонію; ацилювання Наведена інформативна літературна довідка синтетичної значимості реакції ацилювання амінів, продукти якої відповідні аміди є важливими інтермедіатами при отриманні значного масиву практично корисних сполук
N-Acylamino-9,10-anthraquinones became the subject of increased attention of researchers in recent years because of identification of 1-acetamide-9,10anthraquinone as a new mutagenetic metabolite of 1-aminoanthracene [20]. 2-Trifluoroacetamide-9,10anthraquinone was used as a selective colorimetric sensor for a cyanide anion in aqueous solutions [21]
Summary
2l in work [26] on direct acetylation of anilines with ammonium acetate in acetic acid, as well as the experimental data on the absence of reactions when instead of thiocyanate ammonium, thiocyanate potassium or ammonium chloride were used, and direct conversion of 2-amino-9,10-anthraquinone 1e to amide 2h in the reaction with the excess of ammonium acetate in acetic acid. The composition and structure of amides 2a-l synthesized were confirmed by elemental analysis data, mass spectrometry, and 1H, 19F NMR spectroscopy. The new preparative, high yielding method for the synthesis of N-acylated amino-9,10-anthraquinones was introduced
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