Cerium (Iv) Ammonium Nitrate (Can) as a Catalyst in Water: A Simple, Proficient and Green Approach for the Synthesis of Tetrahydropyrimidine Quinolones

Abstract

We report here a facile, mild and efficient synthesis of functionalized tetrahydropyrimidine quinolones via one pot three-component condensation of aromatic aldehydes, N,N-dimethyl barbituricacid (barbituricacid), 4-hydroxy-1-methylquinolin-2(1H)-one and using a cerium ammonium nitrate (CAN) as a green catalyst in aqueous media-water (as a green ideal solvent) is described. The significant advantages of this protocol are short reaction time, simple work up procedure and reduced environmental impact, wide substrate scope; generally very good to excellent yields and starting materials are inexpensive and commercially available. The structures of these compounds were established on the basis of IR, 1 H NMR, 13 C NMR spectra.

Design, characterization, theoretical studies, and dyeing properties of new novel diazo salicylaldehyde Schiff base catalyzed with ceric (IV) ammonium nitrate (CAN) as an eco-friendly catalyst

“…The condensation reaction occurs by refluxing the reaction in the presence of drops of acetic acid as a catalytic reagent (classical method) or in the presence of ceric ammonium nitrate (10 mol %, standard conc.) (Mekheimer et al , 2016; Geramizadegan and Mahdavinia, 2017) stirring at room temperature for a short time about 40 min. The advantage of the reaction in the case of using CAN as a catalyst is that the reaction occurred at room temperature for a short time and without hazards catalyst (green chemistry) in an excellent yield of 92%, compared with the classical method that produced the organic dyes through refluxing in the presence of acetic acid (hazards catalyst) for about 2 h in 81% yield only.…”

Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst

“…Moreover, polyhydroquinoline derivatives exhibited several medicinal applications used to treat Alzheimer ' s disease. [47] Recently, ceric ammonium nitrate (CAN) has been utilized extensively for a broad variety of oxidative transformations in organic chemistry, [48][49][50][51][52][53][54] based on Lewis acidic property due to the generation of protons by hydrolysis of the nitrate anion. Moreover, it is used as a key step for the synthesis of many heterocyclic compounds, [55,56] and it is used as an initiator of radical polymerization reactions.…”

Physicochemical properties of some pyrimidine derivatives in some organic solvents

“…These compounds are known to possess wide spectrum of biological activities such as anti-tubercular, anti-HIV, anti-microbial, anti-analgesic, anti-inflammatory and antimalarial, antidepressant, anticonvulsant, antioxidant, anticancer, antifungal, etc. [4][5][6][7][8][9][10][11][12][13][14][15][16] .…”