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Relevant academic research and scientific papers

Substituent Effects on Pyrid-2-yl Ureas toward Intramolecular Hydrogen Bonding and Cytosine Complexation

Equilibria between two conformational isomers of pyrid-2-yl ureas, the (E,Z) and (Z,Z) forms, have been studied in DMF-d7 at -70 °C. Most of them show a small preference for the (E,Z) form with an equilibrium constant Ki around 1-2. However, the Ki value for 1-methyl-2-(3-(pyrid-2-yl)ureido)pyridinium iodide (12) was found to be 14.2 ± 1.2. That is 1 order of magnitude larger than those of the others, which indicates that the positively charged 1-methylpyridinium-2-yl substituent would facilitate the (E,Z) form formation. Pyrid-2-yl ureas bind cytosine in DMF-d7 with binding constants KB ranging from 30 to 1700 M-1. Electron withdrawing substituents, such as the 4-O 2NC6H4- or 1-methylpyridinium-4-yl substituent, preferentially facilitate the intermolecular cytosine complexation with large binding constants.

Corrosion-protective properties of 1-phenacylmethyl-2- arylcarbamido(arylthiocarbamido)pyridinium bromides

Inhibiting effect of 1-phenacylmethylpyridinium bromides containing urea or thiourea substituents in the pyridinium ring on steel and zinc corrosion in sulfuric acid solutions was studied.

Scalable, One-Pot, Microwave-Accelerated Tandem Synthesis of Unsymmetrical Urea Derivatives

We report a facile, microwave-accelerated, one-pot tandem synthesis of unsymmetrical ureas via a Curtius rearrangement. In this method, one-pot microwave irradiation of commercially available (hetero)aromatic acids and amines in the presence of diphenylphosphoryl azide enabled extremely rapid (1-5 min) construction of an array of unsymmetrical ureas in good to excellent yields. We demonstrate the utility of our method in the efficient, gram-scale synthesis of key biologically active compounds targeting the cannabinoid 1 and α7 nicotinic acetylcholine receptors.

Disubstituted urea compound synthesis method

The invention relates to a synthesis method of disubstituted urea compounds. The synthesis method comprises the following steps: (1) in an air atmosphere, adding amide, arylamine, cuprous iodide and 1,10-phenanthroline to a solvent N-N-dimethylformamide according to a molar ratio of 1:(1.0-2.0):(0.1-0.2):(0.2-0.4) and stirring at 110-130 DEG C till the reaction raw materials disappear; (2) by the end of the reaction, adding excess saturated salt water in to the system, extracting the product with ethyl acetate, washing an organic phase with saturated salt water, drying, and removing the solvent out of the organic phase through a rotary evaporator to obtain a crude product; and (3) purifying the crude product through column chromatography on silica gel in the presence of a developing solvent to obtain a corresponding disubstituted urea compound, wherein the developing solvent is selected according to the thin layer chromatography condition and the polarity condition of the products. The synthesis method of disubstituted urea compounds has the advantages that the raw materials are simple and easily available; the catalyst is cheap, a conventional solvent is used, and air is used as an oxidizing agent; and the operation is simple, the yield is medium to excellent; therefore, the synthesis method has a good development prospect in industrial production.

Synthesis of unsymmetrical 2-pyridyl ureas via selenium-catalyzed oxidative carbonylation of 2-aminopyridine with aromatic amines

A simple, one-pot, phosgene-free approach to a series of unsymmetrical 2-pyridyl ureas starting from 2-aminopyridine and various aromatic amines is reported for the first time. The procedure employs inexpensive selenium as the catalyst, and carbon monoxide (instead of phosgene) as the carbonyl reagent. The products are obtained in moderate to good yields via selenium-catalyzed oxidative cross-carbonylation of the substrate amines in the presence of oxygen. The selenium functions as a phase-transfer catalyst and can be recovered easily and reused without any significant degradation of its catalytic activity.