Synthesis of novel pyrindine derivatives from a facile reaction of 2,5‐bisarylidenecyclopentanone and malononitrile

Abstract

Starting from 2,5‐bisarylidenecyclopentanone and malononitrile (1:1) several novel pyrindine derivatives were synthesized by a facile and convenient one‐pot reaction using sodium ethoxide in absolute ethanol at room temperature. The structure of the reaction products was unambiguously deduced ftom their infrared, 1H‐nuclear magnetic resonance spectroscopy, elemental analysis and single crystal X‐ray crystallography.

Heteroannelation of Cyclic Ketones: Synthesis, Characterization and Antitumor Evaluation of Some Condensed Azine Derivatives

“…The starting material 6 was prepared as described in the literature. 44 The progress of the reaction and the purity of the compounds were routinely monitored on TLC by pre-coated aluminum silica gel 60F 254 thin layer plates obtained from Merck (Germany) eluting with petroleum ether/ethyl acetate. The yields of all products were not optimized.…”

Synthesis of Spiro-fused Hydropyrimidinthiones with Use of Thiobarbituric Acid

“…Удобными многоцентровыми субстратами для синтеза разнообразных гетероциклических систем являются легкодоступные сопряженные диарилметилиденалканоны [1]. Наличие диенонового фрагмента предполагает возможность протекания реакций диполярного циклоприсоединения [2,3], конденсации [3][4][5][6], карбо-и гетероциклизации [7][8][9]. Ранее были изучены превращения бисарилметилиденалканонов с одинаковыми периферическими заместителями [4,6].…”

One-Step Synthesis of Pyridine Derivatives from Malononitrile with Bisarylidenecycloalkanone under Microwave Irradiation

“…For example, reaction of malononitrile with 1,3-diaryl-2-propen-1-ones using sodium alkoxide in ethanol or methanol at room temperature to afford 2,4-diaryl-5-cyano-6-alkoxypyridines (R=CH 3 , C 2 H 5 ), 4 malononitrile with 1,3-diphenylpropenone and other α,β-unsaturated ketones in refluxing methanol / sodium hydroxide to afford 1,4-dipheny-3-cyano-2methoxypyridines and phenyl-substituted [1]benzopyrano- [4,3-b]pyridines, [1]benzothiopyrano [4,3-b]pyridines, pyrido [3,2-b] [1,4]benzothiazines (1-azaphenothiazines) (the yields of 3a and 3d were 59% and 23% respectively), 5 malononitrile with 2,5-bisarylidenecyclopentanones and 2,6diarylidenecyclohexanones using sodium ethoxide in absolute ethanol at room temperature or in refluxing methanol / sodium hydroxide to give 3-cyano-2-alkoxypyridine derivatives. [6][7] However, reaction times were long and yields were low by classical methods.…”