The Investigation of Michael Addition of Acetoacetanilide and Methyl Acetopyruvate to Some Ylidenecyanoacetamides

Abstract

It was established that by the Michael addition of substituted ylidenecyanoacetamides with acetoacetanilide in methanol media and in the presence of methyl piperazine at room temperature, various new substituted pyridone derivatives were formed. Also, by the interaction of 2-fluorobenzylidenecyanoacetamide and methyl acetopyruvate in the methanol media, in the presence of methyl piperazine corresponding pyridone derivative was synthesized. Structures of all synthesized compounds confirmed by NMR spectroscopy. ASETOASETANİLİD VƏ PİRUVAT TURŞUSUNUN METİL EFİRİNİN BƏZİ İLİDENSİANOAMİDLƏRƏ MİXAEL BİRLƏŞMƏ REAKSİYASININ TƏDQİQİ F.N.NağıyevƏvəzlənmiş ilidensianoasetamidlər ilə asetoasetanilidin Mixael birləşmə reaksiyası metanol mühitində, metilpiperazin iştirakında, otaq temperaturunda aparılmış və reaksiyadan yeni əvəzlənmiş piridon törəmələrinin əmələ gəldiyi müəyyən edilmişdir. Eləcə də metanol mühitində, metilpiperazin iştirakında, piridilidensianoasetamid, 2-flüorbenzilidensianoasetamidin methyl acetopiruvate ilə qarşılıqlı təsir reaksiyasından uyğun əvəzlənmiş piridon törəməsi sintez edilmişdir. Structures of all synthesized compounds confirmed by NMR spectroscopy.Açar sözlər: ilidensianoasetamidlər, 2-flüorbenzilidensianoasetamid, asetoasetanilid, metil asetopiruvat. ИССЛЕДОВАНИЕ ПРИСОЕДИНЕНИЯ ПО МИХАЭЛЮ НЕКОТОРЫХ ИЛИДЕНЦИАНО-АЦЕТАМИДОВ К АЦЕТОАЦЕТАНИЛИДУ И МЕТИЛАЦЕТОПИРУВАТУ Ф.Н.НагиевУстановлено, что реакцией присоединения по Михаэлю илиденцианоацетамидов к ацетоацетанилиду в среде метанола в присутствии метилпиперазина при комнатной температуре образуются различные новые замещенные производные пиридона. Также взаимодействием 2-фторбензилиденцианоацетамида и метилацетопирувата в среде метанола и в присутствии метилпиперазина синтезировано соответствующее замещенное производное. Структуры всех синтезированных соединения подтверждены методом 1 H и 13 C ЯМР.

Crystal Structure and Hirshfeld Surface Analysis of Acetoacetanilide Based Reaction Products

“…In the context of our research program aimed at exploring the utility of acetoacetanilide 1 in multicomponent synthesis, we have recently reported a series of transformations illustrated in Scheme 1 [ 14 , 15 , 16 , 17 ]. Several double Michael acceptors bearing cyano groups at the α-position were found to give rise to structurally diverse heterocyclic products 2 – 5 when reacted with 1 in the presence of piperazine catalysts.…”

“…Preparation of 2 and 4 was performed according to procedures reported in our previous papers [ 14 , 15 ]. Single crystals of title compounds were grown from ethanol solution by slow evaporation.…”

Synthesis of Some Functionalized Pyridones Derivatives

“…Ciclopirox, milrinone, camptothecin, (-)-citisin, fredericamycin, perampanel, bioactive molecules and pharmaceutical ingre-dients contain valuable pyridone fragments in their composition. Also, synthesis methods of these compounds are different from in reaction conditions in literature [1][2][3][4][5][6][7][8][9][10][11][12]. Some articles [13-17] research into antimicrobial activity of pyridone derivatives.…”