An efficient synthesis of N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide via enolate salts

About the reaction of β‐dimethylamino‐α,β‐enones with active methylene nitriles

“…Pyridines and pyridones represent an important class of these compounds because of their pharmaceutical applications [6][7][8]. The reaction of enaminones with active methylene nitriles represents one of the strategies for the preparation of 2-1H-pyridone [9][10][11]. 3-Dimethylamino-1-arylpropenones 1a-c have been extensively used in the last years by Elnagdi and coworkers for the synthesis of pyridones [12][13][14].…”

TWO-STAGE ONE-POT INTERACTION OF ACYCLIC Β-Ketoesters, DMFDMA AND 2-Cyanomethylbenzimidazole

“…In the earlier papers of our group [8,10] enamines 21 were shown to react with N-substituted cyanoacetamides 22 via intermediate formation of resonance-stabilized enolates 23 (Scheme 5) similarly to Path B (Scheme 4). The intermediates 23 were isolated as precipitates and their structure was defined in X-ray diffraction study [9]. In addition the condensation of cyclic 1,3-dicarbonyl compounds of type 1 with DMFDMA 2 and 2-(1H-benzo[d]imidazol-2-yl)acetonitrile 4 (Scheme 1) resulted in selective formation of cyanides 5 and our attempts to isolate other types of reaction products by variation of reaction conditions were unsuccessful [18].…”

“…Working in this field we studied previously several variations of a one-pot reaction between α-CH 2 -carbonyl compounds, dimethylformamide dimethylacetal (DMFDMA) and active methylene nitriles giving a great diversity of heterocyclic compounds of different classes [8][9][10][11][12][13]. Selectivity and pathways of such transformations depend on both the reaction conditions and the structure of initial compounds.…”

Syntheses of Enaminone-Based Heterocyclic Compounds and Study their Biological Activity

“…Enaminones are versatile precursors that have been utilized extensively as building blocks in organic synthesis [3][4][5][6][7][8][9][10][11][12] , such compounds are synthetic precursors for the synthesis of a broad diverse of naturally occurring alkaloids 13 and nitrogen-containing heterocycles 14 .…”