Green and Facile Synthesis of Pyrimidine Derivatives Using Choline Chloride-urea Mixture as a Deep Eutectic Solvent or Cerium (IV) Ammonium Nitrate

Abstract

An efficient and facile synthesis of substituted pyrimidine derivatives through Biginelli type reaction was achieved in high yields via one-pot reaction of aromatic aldehydes, active methylene compounds and urea or thiourea in the presence of choline chloride- urea mixture as a deep eutectic solvent or cerium (IV) ammonium nitrate (CAN) as a catalyst at different conditions. The reaction was carried out using different ratio of CAN in different solvents to determine the optimum conditions. In addition, 2-mercapto-6-oxo- 4-(thiophen-2-yl)-1,6-dihydropyrimidine-5-carbonitrile was employed in the synthesis of pyrimidinylhydrazide and its corresponding hydrazone. The structural formula of all derivatives was confirmed and characterized by their elemental analyses and spectral data (IR, MS, 1H NMR, 13C NMR).

Green design of novel heterocycles using deep eutectic solvent and evaluation of their cytotoxicity and antioxidant activities

“…Recently, deep eutectic solvents (DESs) have appeared in green chemistry as promising alternatives to other organic solvents due to their low volatility, nonflammability and high thermal stability which promote their uses in many organic transformations and reactions (1)(2)(3)(4)(5). Additionally, DESs have the advantages of being recyclable and inexpensive can be used in stoichiometric amounts as catalyst (6,7).…”

Green synthesis, cytotoxicity and antimicrobial activities of some new pyrazolines, pyrimidines and naphthyridines based on 1,3-di(thien-2-yl)prop-2-en-1-one using choline chloride-urea mixture as a deep eutectic solvent

“…In recent years, deep eutectic solvents (DESs) have attracted great attention as green solvents in many organic reactions and transformations [1][2][3][4][5][6][7][8]. DESs can be easily formulated via hydrogen bonding between two components, the first is hydrogen bond donor which can be acid [9], alcohol [10,11] carbohydrate [12] or amide [13,14] and the second is hydrogen bond acceptor as quaternary ammonium salt [14,15].…”

Bio‐based benzoxazines synthesized in a deep eutectic solvent: A greener approach toward vesicular nanosystems

“…[12,13] Abbott et al reported facile synthesis of eutectic liquid from choline chloride [ (2-hydroxyethyl) trimethylammonium chloride] and urea as renewable starting materials in a molar ratio of 1:2 showing interesting solvent properties and a melting point lower than those of the individual components. [15] On the other hand, 1,3-benzoxazine derivatives (BZs) are one of the most important heterocycles owing to their remarkable antibacterial and antifungal activities, [16][17][18] anticancer, [19,20] analgesic, [21] antiplatlet, [22] and antimycobacterial activity. [15] On the other hand, 1,3-benzoxazine derivatives (BZs) are one of the most important heterocycles owing to their remarkable antibacterial and antifungal activities, [16][17][18] anticancer, [19,20] analgesic, [21] antiplatlet, [22] and antimycobacterial activity.…”