One‐pot synthesis of pyrido[2,3‐d]pyrimidines via efficient three‐component reaction in aqueous media

Abstract

A short and facile synthesis of pyrido[2,3-d]pyrimidine derivatives was accomplished in good yields via the three-component reaction of aldehydes, alkyl nitriles and aminopyrimidines in water in the presence of triethylbenzylammonium chloride (TEBAC). The structures of these compounds were characterized by elemental analysis, IR and 1 H NMR spectra and further confirmed by single crystal X-ray diffraction analysis.

One-Pot Synthesis of Novel Derivatives of Dithioxopyrido[2,3-d:6,5-d’]dipyrimidine-4,6-diones Using Hap-Encapsulated γ-Fe2O3 Supported Sulfonic Acid Nanocatalyst

“…Several approaches have been developed for the synthesis of pyridopyrimidines [28,29], such as the reaction of benzylidene derivatives of malononitrile with 6-amino-3,4-dihydropyrimidine in refluxing ethanol [30,31]; the reaction of 6-amino-1-thio uracil with ethyl-3-phenyl-2-cyanoacrylate in absolute ethanol and in the presence of Et3N by heating [32,33]; the three-component reaction of aldehydes, alkyl nitriles and aminopyrimidines in water and in the presence of KF-Al 2 O 3 as catalyst [34]; the threecomponent reaction catalyzed by triethyl benzyl ammonium chloride (TEBAC) [35] or reaction of amino-uracil with α,β-unsaturated compounds in ionic liquid at 90˚C [36]. Some of the reported methods suffer from disadvantages such as multi-step synthesis with the use of expensive harmful reagents, low yields and longer reaction times.…”

Electrocatalytic multicomponent assembling of aminouracils, aldehydes and malononitrile: An efficient approach to 7-amino-pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives

“…12 Several synthetic methodologies for the synthesis of 7-aminopyrido[2,3-d]pyrimidine-6-carbonitrile derivatives have been reported. [13][14][15][16][17] However, in spite of their potential utility, most of the reported synthetic methods suffer from limitations, such as the use of expensive catalysts, long reaction times, difficult work--up and commercial non-availability. Therefore, any new, facile and highly efficient synthetic approach to corresponding 7-aminopyrido[2,3-d]pyrimidine-6--carbonitrile derivatives is welcome.…”

Clean and Efficient Synthesis of Pyrazole Derivatives in Aqueous Media

“…However, these syntheses are usually carried out in organic solvents. As part of our current studies on the development of new routes to heterocyclic systems in aqueous media , we now report an efficient and clean synthetic route to pyrazole and isoxazole derivatives via the reaction of 3‐(dimethylamino)‐1‐arylprop‐2‐en‐1‐one with hydrazine or hydroxylamine in aqueous media.…”