2327-17-5

Usage

InChI:InChI=1/C12H11N3O/c16-12(14-10-6-2-1-3-7-10)15-11-8-4-5-9-13-11/h1-9H,(H2,13,14,15,16)

Upstream product

• 504-29-0 2-aminopyridine 
• 4910-32-1 1,3-diphenylcarbamothioate 
• 121-44-8 triethylamine 
• 103-71-9 phenyl isocyanate 
• 65478-59-3 2H-<1,2,4>oxadiazolo<2,3-a>pyridine-2-thione 
• 62-53-3 aniline 
• 109-09-1 2-chloropyridine 
• 64-10-8 phenyl carbamate 
• 55-21-0 benzamide 
• 500-72-1 oxanilic acid 
• 591-50-4 iodobenzene 
• 199620-14-9 chromium⁽⁰⁾ hexacarbonyl 
• 201230-82-2 carbon monoxide 
• 582-61-6 benzoyl azide 

Downstream Products

• 58634-06-3 N-(1-oxy-[2]pyridyl)-N'-phenyl-urea 
• 677326-92-0 4-(3-pyridin-2-yl-ureido)-benzenesulfonyl chloride 
• 392692-37-4 1-{4-[4-({3-[4-(tert-butyl-diphenyl-silanyloxy)-phenoxy]-2-hydroxy-propylamino}-methyl)-piperidine-1-sulfonyl]-phenyl}-3-pyridin-2-yl-urea 
• 392691-45-1 1-[4-(4-aminomethyl-piperidine-1-sulfonyl)-phenyl]-3-pyridin-2-yl-urea 

Relevant academic research and scientific papers

Synthesis of unsymmetrical urea from aryl- or pyridyl carboxamides and aminopyridines using PhI(OAc)2via in situformation of aryl- or pyridyl isocyanates

A tandem synthesis of unsymmetrical ureas (N-aryl-N′-pyridylurea andN,N′-bipyridylurea) from aryl- or pyridyl carboxamides and aminopyridinesviaHofmann rearrangement has been reported. In particular, benzamides, picolinamide, nicotinamide, and isonicotinamide generate reactive intermediate isocyanates,in situ, in the presence of PhI(OAc)2, which upon further reaction with aminopyridines form urea derivatives. As the formation of pyridylisocyanates from their corresponding carboxamidesviaHofmann rearrangement remained unexplored previously, attempts have been made to trap the isocyanates. While the three pyridylisocyanates were trapped as their corresponding carbamates, 3-pyridylisocyanate was isolated and characterized. Unlike closely related previous methods reported for urea synthesis, the current method avoids direct use of isocyanates or eliminates the use of toxic phosgene for thein situgeneration of isocyanates.

Photocatalyzed synthesis of unsymmetrical ureas via the oxidative decarboxylation of oxamic acids with PANI-g-C3N4-TiO2 composite under visible light

The synthesis of unsymmetrical ureas via the photocatalyzed oxidative decarboxylation of oxamic acids has been developed. The carbamoyl radicals were generated from oxamic acids in the presence of a hypervalent iodine reagent and the PANI(Polyaniline)-g-C3N4-TiO2 composite under visible light irradiation. The radicals were converted in situ into the corresponding isocyanates, which were then trapped by amines to afford the corresponding products in moderate to good yields. This protocol avoided the direct use of environmentally unfriendly isocyanates and a series of substrates were tolerated. Moreover, the photocatalyst could be readily recovered by simple filtration and be reused for several runs with only a slight decrease in the catalytic activity.

Metal-free synthesis of pyridin-2-yl ureas from 2-aminopyridinium salts

An unprecedented base promoted domino approach has been developed for the synthesis of pyridin-2-yl urea derivatives via the reaction of 2-aminopyridinium salts and arylamines. The developed strategy tolerated a wide range of functional groups and afforded pyridin-2-yl ureas in moderate to good yields. The reaction was postulated to involve tandem cyclization, intermolecular nucleophilic addition, ring opening, and demethylation.

Palladium-Catalyzed Synthesis of Symmetrical and Unsymmetrical Ureas Using Chromium Hexacarbonyl as a Convenient and Safe Alternative Carbonyl Source

Pd-catalyzed synthesis of urea derivatives from aryl iodides and different aliphatic and aromatic amines using sodium azide and chromium hexacarbonyl is described. In this process, carbonylation of aryl iodides, Curtius rearrangement of aroyl azides, and nucleophilic addition of amines sequentially occur to afford the products in good to excellent yields. This protocol is operationally simple and displays a broad substrates scope.

(Thio)urea-catalyzed friedel-crafts reaction: Synthesis of bis(indolyl)-methanes

Bis(indolyl)methane derivatives (BIMs) were synthesized in moderate to good yields by (thio)urea catalyzed electrophilic substitution of indole (2) with various aldehydes 1. Reactions were performed under conventional and microwave (MW) heating, either using 1,2-dichloroetane as solvent or without solvent. The procedure using microwave heating was also applied to the synthesis of the natural products vibrindole A (3n), arsindoline A (3i), arundine (3o) and tris(1H-indol-3-yl)methane (3j). Additionally, the synthesis of streptindole was carried out via intermediate 3g. This methodology is well suited for the synthesis of bis(indolyl)methanes: it offers good yields of products, low sensitivity to moisture and oxygen, high tolerance to different functional groups on the aldehydes such as al-kynes and trimethylsilane, and simplicity in operation

Glucokinase Activators Based on N-Aryl-N′-Pyridin-2-Ylurea Derivatives

A series of previously undescribed N-aryl-N′-pyridin-2-ylureas were prepared via the reaction of 2-aminopyridines with benzoyl azides and tested in vitro as activators of glucokinase. Statistically significant reductions of glucose levels as compared with

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.

ORGANIC MOLECULES FOR TERAHERTZ TAGGING APPLICATIONS

The present invention discloses substituted heterocyclic compounds and /or aromatic compounds containing amide and/or urea groups exhibiting resonance in the range of 0.1- 10 THz. The invention also discloses binary molecular complexes based on the substituted heterocyclic compounds and/or aromatic compounds containing amide and/or urea groups of the present invention. The compounds and binary molecular complexes of the present invention have varying molecular mass and hydrogen bond strengths demonstrating several resonances below 10 THz. The compounds and binary molecular complexes of the present invention are customizable for various applications, such as authentication of a product.

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.

Synthesis of polynuclear azoles linked through carbamate and urea bridges

Polynuclear azoles linked through carbamate and urea fragments were synthesized by reactions of the corresponding azolecarboxylic acid azides with heterocyclic alcohols and amines. Pleiades Publishing, Ltd., 2012.