A facile synthesis of 6‐alkoxy‐2,4‐diaryl‐5‐cyanopyridine

Abstract

A new synthesis of substituted pyridine is reported. The base catalyzed reaction of substituted chalcones with malononitrile using sodium ethoxide in ethanol at room temperature afforded 2,4‐diaryl‐5‐cyano‐6‐ethoxypyridine. Similarly, 2,4‐diaryl‐5‐cyano‐6‐methoxypyridine have been prepared in presence of sodium methoxide in methanol as a catalyst.

Hirshfeld Surface, Molecular Docking Study, Spectroscopic Characterization and NLO Profile of 2‐Methoxy‐4,6‐Diphenylnicotinonitrile

“…2‐Amino‐3‐cyanopyridine derivatives are valuable heterocyclic compounds possessed broadcast biological activity and due to its chelating agent ability it can be used as ligand in organometallic chemistry . The title compound 2‐methoxy‐4,6‐diphenylnicotinonitrile was obtained according to the reported method by the reaction of α , β ‐unsaturated ketone with malononitrile in the presence of sodium methoxide and absolute methanol . In the literature, a short synthesis study on 2‐methoxy‐4,6‐diphenylnicotinonitrile was made by Tyndall et al.…”

“…[1,3,10] The title compound 2-methoxy-4,6-diphenylnicotinonitrile was obtained according to the reported method by the reaction of α,β-unsaturated ketone with malononitrile in the presence of sodium methoxide and absolute methanol. [2,11] In the literature, a short synthesis study on 2-methoxy-4,6diphenylnicotinonitrile was made by Tyndall et al. [12] Aminopyridine-based monopolar spindle 1 (Mps1) kinase, known as TTK, is a dual-specificity kinase having an important role for the spindle assembly check point and its over expression are observed in tumor cells.…”

Cyanoacetanilides Intermediates in Heterocyclic Synthesis. Part 1: A Facile Synthesis of Polysubstituted and Condensed Pyridones

“…1 H NMR of 5a revealed two singlets at d = 8.1, 10.2 ppm assignable to two NH groups and a multiplet at d = 7.3-7.8 ppm assigned for aromatic protons. The formation of 5 assumed to proceed via Michael addition of the active methylene to the a,b-unsaturated ketone to yield the Michael adduct 3 followed by intramolecular cyclization to form 4 and subsequent Dimrouth rearrangement 16 to yield 5 (Scheme I). Also, interaction of 1b with 1,1,3-tricyano-2-aminopropene 6 in the presence of piperidine yielded a single product that analysed as C 15 H 8 ClN 5 O.…”

Synthesis and Anticonvulsant Activity of Novel 2- and 3-14-(Trisubstituted Pyridy1)-phenylaminol- and 2-[3- and 4-(Trisubstituted Pyridy1)-phenoxylquinoxaline Derivatives

“…To a cooled freshly prepared sodium alkoxide solution (0.04 mol, 0.92 g of sodium in 150 ml absolute methanol or ethanol) was added a mixture of compound 2 (5.95 g, 0.02 rnol), malononitrile (1.32 g, 0.02 rnol), and the appropriate aldehyde (0.02 mol) in absolute methanol or ethanol (40 rnl), respectively, with continuous stirring for 8-10 h. The precipitated solid was collected by filtration, dried, and recrystallized from the suitable solvent. ir, 18 (22). A mixture of 2,3-dichloroquinoxaline (1) (1.99 g, 0.01 rnol), 4-hydroxyacetophenone (1.36 g, 0.01 rnol), and anhydrous potassium carbonate (3.18 g, 0.03 mol) in absolute ethanol (50 ml) was stirred for 20 h. The reaction mixture was allowed to stand overnight at room temperature, the solid separated was collected by filtration and recrystallized from ethanol to yield 1.97 g (66%) of 22, mp 138-140 "C. ir: 1667 (CO).…”