Synthesis of functionalized alkyl-substituted cyclohexanones, pyridines, and 2,3,5,6,7,8-hexahydroisoquinolines by condensation of aliphatic aldehydes with CH acids

The Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazol-4-carbonitrile with beta-Cycloketols

“…However, the heterocyclization reactions of β-cycloketols are not well studied. Thus, the literature describes the preparation of isoquinolines 2 [3][4][5][6][7], indazoles 3 [8][9][10], benzo[c]isoxazoles 4 [9,10], [1,2,4]triazolo [3-b]quinazolines 5 [11] and pyrazolo[3-c]isoquinolines 6 [12] (Scheme 1) by reactions of beta-cycloketols with various 1,2-and 1,3-dinucleophilic agents. Despite the large attention paid to reactions of aminoazoles with 1,3-dielectrophilic agents (see reviews [13,14]), only a few examples of reactions involving β-cycloketols were found in the literature.…”

Synthesis of 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile by condensation of cyanothioacetamide with acetaldehyde and 1-(prop-1-en-2-yl)piperidine

“…In continuation of our studies on the synthesis of alkyl-substituted pyridinechalcogenones starting from aliphatic aldehydes [9][10][11][12], in the present work we examined three-component condensation of cyanothioacetamide (1), acetaldehyde (2), and 1-(prop-1-en-2yl)piperidine (3) in anhydrous ethanol at 20°C. As a result, we isolated 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile (4) which was synthesized previously by condensation of acetylacetone with cyanothioacetamide [13], as well as by Michael-type reaction (exchange of methylene components) of 2-cyano-2-cyclohexylidenethioacetamide with acetylacetone [14].…”