- Copper(II)-Catalyzed Reactions of α-Keto Thioesters with Azides via C-C and C-S Bond Cleavages: Synthesis of N-Acylureas and Amides
-
Cu(II)-catalyzed reaction of α-keto thioesters with trimethylsilyl azide (TMSN3) proceeds with the transformation of the thioester group into urea through C-C and C-S bond cleavages, constituting a practical and straightforward synthesis of N-acylureas. When diphenyl phosphoryl azide (DPPA) is used instead as the azide source in an aqueous environment, primary amides are formed via substitution of the thioester group. The reactions are proposed to proceed through Curtius rearrangement of the initially formed α-keto acyl azide to generate an acyl isocyanate intermediate, which reacts further with an additional amount of azide or water and rearranges to afford the corresponding products. To demonstrate the potentiality of the method, one-step syntheses of pivaloylurea and isovaleroylurea, displaying anticonvulsant activities, have been carried out.
- Maity, Rajib,Naskar, Sandip,Das, Indrajit
-
p. 2114 - 2124
(2018/02/23)
-
- Gentle method for carbonylation and arylation reaction of urea compounds
-
The invention discloses a gentle method for carbonylation and arylation reaction of urea compounds. The method includes a step of performing a coupling carbonylation reaction to a halogenated aromatic compound with a urea compound under a gentle condition to produce a ureide compound, palladium acetate being a catalyst, triethylamine being an alkali, and pentacarbonyl iron being a CO release source. The method has simple operations and gentle reaction condition, is low in usage amount of the catalyst and the CO release source, is low in toxicity and cost, has wide substrate applicability and high yield of the target product, and can be widely applied to preparation of a ureide compound medicine molecule.
- -
-
Paragraph 0015-0019; 0020; 0021; 0022; 0023; 0024
(2018/01/12)
-
- Synthesis of imides and benzoylureas by direct oxidation of N-methylenes of amides and benzylureas
-
Some amides and benzylureas can be oxidised to imides and benzoylureas, respectively, using silver(I) nitrate (20 mol %), copper(II) sulfate pentahydrate (20 mol %), ammonium persulfate (3.0 equiv.), and potassium fluoride (20 equiv.) in water at room temperature.
- Huang, Wenhua,Xu, Mei-Li
-
-
- Solid-phase synthesis of disubstituted N -acylureas from resin-bound ureas and acyl chlorides
-
Acylureas (ureides) are valued for their important biological activities. Whereas cyclic acylureas have frequently been the object of solid-phase chemistry, only few reports have focused on the solid-supported preparation of acyclic representatives. We have prepared different types of acylureas on Rink amide resin in three or four steps. The products are either N-acylated (9, 18), N-acylated-N′-alkylated (10, 19), or N-acylated-N-alkylated (22). Characteristic NMR parameters of isomeric acylureas 10, 19, and 22 are discussed.
- Haecker, Hans-Georg,Meusel, Manuela,Aschfalk, Melanie,Guetschow, Michael
-
experimental part
p. 59 - 64
(2011/04/15)
-
- Novel two-step, one-pot synthesis of primary acylureas
-
A new procedure for the synthesis of primary acylureas from cyanamide and a variety of carboxylic acids is described. Under mild reaction conditions, the products were obtained in good yield from commercially available starting materials.
- Xiao, Zili,Yang, Michael G.,Tebben, Andrew J.,Galella, Michael A.,Weinstein, David S.
-
experimental part
p. 5843 - 5844
(2010/11/05)
-
- Aminobenzoic acid derivatives having anti-tumorigenic activity methods of making and using the same
-
Haloacetoamido, benzoic acid derivatives having anti-tumorigenic activity are inclosed. Examples of the haloacetoamido, benzoic acid derivatives include 3-chloroacetoamido, benzoylurca, 3-bromoacctoamido, benzoylurea, 3-todoacetoamido, benzoylurca, ethyl-3-chloroacetoamido, benzoate, ethyl-3-bromoacetoamido, benzoate and ethyl-3-iodoacetoamido, benzoate. Intermediates for synthesizing the derivatives, along with method of making and using the derivatives, are also provided.
- -
-
-
- Process for preparing 2-oxindole-1-carboxamides
-
The present invention provides a process for preparing 2-oxindole-1-carboxamides, comprising reacting N-acyl 2-oxindole-1-carboxamides with alcohols in the presence of aprotic weak Lewis acid catalysts. In certain processes of the present invention a 2-oxindole-1-carboxamide is prepared from a 2-oxindole by reacting the 2-oxindole with an acyl isocyanate to produce the N-acyl 2-oxindole-1-carboxamide as an intermediate, which is then reacted with alcohol in the presence of aprotic weak Lewis acid catalysts. The N-acyl 2-oxindole-1-carboxamide intermediate may be converted to the 2-oxindole-1-carboxamide without isolation.
- -
-
-
- Nucleophilic substitution of urea on aromatic carboxylic acids via phosphorylation
-
The nucleophilic substitution reaction of urea on aromatic carboxylic acids has been carried out via phosphorylation.Five different carboxylureas have been synthesised in good yields and with high purity.This new route makes the existing corrosive acid chloride route easier and can be used as a general route for the preparation of any acid-urea substitution product.The products have been characterized by elemeental analyses and spectral data (IR, PMR and mass).
- Prabhakaran, P V,S, Jayadev,Nema, S K,Rao, K V C
-
p. 1072 - 1073
(2007/10/02)
-
- Benzoyl-ureas having insecticide activity
-
Compounds are disclosed having formula: STR1 wherein: R is Cl, F; R1 is H, Cl, F; R2 and R5, equal to or differing from each other, are H, halogen, alkyl C1 -C4 ; R3 and R4, equal to or differing from each other, are: H, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy or alkynyl; Z is O, S or a group NR7, wherein R7 is alkyl C1 -C3 or H; Y is alkylene C2 -C4, haloethylene or haloethenyl; R6 is alkyl C1 -C4, haloalkyl C1 -C4, alkenyl C3 -C4, haloalkenyl C3 -C4, cycloalkyl C3 -C4, halocycloalkyl C3 -C4 or cycloalkenyl C3 -C4. The compounds having formula (I) are endowed with an elevated insecticide activity, which shows itself chiefly against insect larvae and eggs.
- -
-
-
- N-(halobenzoyl)-N'-2-halo-4-[1,1,2-trifluoro-2-(trifluoro-methoxy)ethoxy]-phenyl-ureas with insecticide activity
-
A class of particularly active insecticide compounds: N-(halobenzoyl)-N?-2-halo-4-[1,1,2-trifluoro-2-(trifluoro--methoxy)ethoxy)-phenyl-ureas, the preparation of such compounds and their use in the fight against the infestations by insects is disclosed.
- -
-
-
- Heterocyclic Photorearrangements. Photochemical Behaviour of Some 3,5-Disubstituted 1,2,4-Oxadiazoles in Methanol at 254 nm
-
Photochemical behaviour of some 3,5-disubstituted 1,2,4-oxadiazoles in methanol at 254 nm has been investigated.Ring photoisomerization to the 1,3,4-oxadiazole heterocycle or formation of open chain compounds involving the nucleophilic solvent was shown to depend on the nature and the position of the substituent.Photoinduced ring closure into the benzimidazole system, involving a 3-N-phenylamino side chain sequence and a photolytic intermediate of the oxadiazole heterocycle, is also reported.
- Buscemi, Silvestre,Cicero, Maria G.,Vivona, Nicolo,Caronna, Tullio
-
p. 931 - 935
(2007/10/02)
-
- N-(2,6-difluorobenzoyl)-N'-3-chloro-4-[1,1,2-trifluoro-2-(trifluoromethoxy) ethoxy] phenyl urea having insecticidal activity
-
A particularly active insecticidal compound: N-(2,6--difluorobenzoyl)-N′-3-chloro-4- [ 1,1,2-trifluoro-2-(trifluoro-methoxy) ethoxy ] phenyl urea, insecticidal compositions contain-ing it as active ingredient, and the use thereof for fighting insect infestations.
- -
-
-
- Benzoyl-ureas having insecticide activity
-
Compounds are specified having formula: wherein:, R = C1, F; R1 = H, C1, F; R2 and R5, equal to or differing from each other, are: H, halogen, alkyl C1-C4;, R3 and R4, equal to or differing from each other, are: H, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, halo-alkenyl, alkenyloxy, haloalkenyloxy, or alkynyl;, Z = O, S or a group = NR7, wherein R7 is alkyl C1-C3 or H; Y = alkylene C2-C4, haloethylene or haloethenyl;, R6 = alkyl C1-C4, haloalkyl C1-C4, alkenyl C3-C4, haloalkenyl C3-C4, cycloalkyl C3-C4, halocycloalkyl C3-C4 or cycloalkenyl C3-C4., The compounds having formula (I) are endowed with an ele-vated insecticide activity, which shows itself chiefly against insect larvae and eggs.
- -
-
-
- Benzoylureas
-
Insecticidally and acaricidally active novel compounds of the formula STR1 in which A is --CF2 --CF2 --, --CF2 --CHF-- or --CF2 --CFCl--, X is oxygen or sulphur, R1, R2 and R3 each independently is hydrogen, halogen or alkyl, R4 and R5 each independently is hydrogen, halogen, alkyl or halogenoalkyl, and R6 is hydrogen, halogen or alkyl. The benzodioxene intermediates therefor are also new.
- -
-
-
- Photo-oxidation of Oxazolidones and Hydantoins in the Presence of Benzophenone
-
Irradiation in the presence of benzophenone and oxygen of nitrogen-containing heterocycles having an NCO group yields products arising out of regioselective oxidation α to the nitrogen atom.Direct irradiation (in the absence of benzophenone and oxygen) of 5-methyl- and 5,5-dimethyl-hydantoins yields allophanates.The first step of this reaction involves the homolysis of the C(4) - C(5) bond of the hydantoin.
- Gramain, Jean-Claude,Remuson, Roland
-
p. 2341 - 2346
(2007/10/02)
-
- Sensitized Photooxygenation of 2-Amino-4-phenylthiazole
-
2-Amino-4-phenylthiazole (1) on photooxygenation affords a compound which has been characterised by chemical degradations and spectral evidences as thiobenzoylurea (2).Surprisingly, 2-methyl-4-phenylthiazole does not undergo photooxygenation.
- Bahar, M. H.,Sabata, B. K.
-
p. 870 - 872
(2007/10/02)
-
