4-Functionally Substituted 3-Heterylpyrazoles: IV. Benzylamino[3-aryl(heteryl)-4-pyrazolyl]methylphosphonic Acids

Derivatives of N-benzyl[3-aryl(heteryl)-4-pyrazolyl]methanimines react with diethyl phosphite to afford diethyl benzylamino[3-aryl(heteryl)-4-pyrazolyl]-4-methylphosphonates that on hydrolysis with 18% hydrochloric acid yield the corresponding aminophosphonic acids.     

4-Functionally Substituted 3-Heterylpyrazoles: XIII. 3-Aryl(heteryl)-4-(4-pyrazolyl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones)

Cyclocondesation of 3-aryl(heteryl)pyrazole-4-carbaldehydes with ethyl acetoacetate and urea (thiourea) in the presence of FeCl₃ · 6H₂O afforded 3-aryl(heteryl)-4-(4-pyrazolyl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 97–98.Original Russian Text Copyright © 2005 by Bratenko, Chornous, Vovk.     

4-Functionally Substituted 3-Heterylpyrazoles: VII. 3-Aryl(heteryl)-1-phenyl-4-pyrazolecarbonyl Isothiocyanates

3-Aryl(heteryl)-1-phenyl-4-pyrazolecarbonyl isothiocyanates were synthesized by treatment of 3-aryl(heteryl)-1-phenyl-4-pyrazolecarbonyl chlorides with lead, sodium, or ammonium thiocyanate. Their reactions with amines, hydrazines, and acylhydrazines gave the corresponding thioureas and thiosemi- carbazides.     

4-Functionally Substituted 3-Heterylpyrazoles: VIII. 3-Aryl(heteryl)-4-hydroxyl(chloro)methylpyrazoles

3-Aryl(heteryl)pyrazole-4-carbaldehydes were reduced with sodium tetrahydridoborate under mild conditions to give 3-aryl(heteryl)-4-hydroxymethylpyrazoles which were converted into the corresponding 4-chloromethyl derivatives by treatment with thionyl chloride. The subsequent reaction with triphenylphos- phine led to formation of triphenyl(4-pyrazolylmethyl)phosphonium chlorides, and Wittig reaction of the latter with aromatic or heteroaromatic aldehydes yielded 4-[2-aryl(heteryl)ethenyl]pyrazoles.     

4-Functionally Substituted 3-Heterylpyrazoles: III. 3-Aryl(heteryl)pyrazole-4-carboxylic Acids and Their Derivatives

3-Aryl(heteryl)-4-formylpyrazoles were cleanly oxidized by potassium permanganate in water-pyridine medium to afford in high yield 3-aryl(heteryl)pyrazole-4-carboxylic acids, that were further converted into the corresponding chlorides and amides.     

Functionally Substituted 3-Heterylpyrazoles: IX. 3-Aryl(heteryl)-4-mercapto(thiocyanato,isothiocyanato)methylpyrazoles

By reaction of 3-aryl(heteryl)-4-chloromethylpyrazoles with thiourea and sodium thiocyanate respectively 3-aryl(heteryl)-4-mercaptomethylpyrazoles and 3-aryl(heteryl)-thiocyanatomethylpyrazoles were obtained. The latter were subjected to thermal isomerization into 3-aryl(heteryl)-isothiocyanatomethylpyrazoles.     

Functionally Substituted 3-Heterylpyrazoles: XI. 3-[3-Aryl(heteryl)pyrazol-4-yl]propenoic and Propanoic acids

3-Aryl(heteryl)-4-formylpyrazoles by condensation with malonic acid furnish 3-[3-aryl(heteryl)- pyrazol-4-yl]propenoic acids that in the presence of Raney nickel are reduced by hydrazine hydrate to 3-[3-aryl(heteryl)pyrazol-4-yl]propanoic acids. The successive conversion of both type acids into the corresponding acyl chlorides, esters, and amides was performed.     

4-Functionally-substituted 3-Heterylpyrazoles: XV. 3-Aryl(heteryl)-1-phenyl-4-pyrazolylmethylamines and Heterocumulenes Obtained Therefrom

By reduction of 3-aryl(heteryl)-1-phenyl-4-azidomethyl-pyrazoles in the presence of Raney nickel or by hydrazinolysis of N-[3-aryl(heteryl)-1-phenyl-4-pyrazolylmethyl]phthalimides 4-pyrazolylmethylamines were obtained that in reaction with bis(trichloromethyl) carbonate afforded 3-aryl-(heteryl)-1-phenyl-4-pyrazolylmethyl isocyanates, and with carbon disulfide furnished 3-aryl-(heteryl)-1-phenyl-4-pyrazolylmethyl isothiocyanates.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 247–251.Original Russian Text Copyright © 2005 by Bratenko, Panimarchuk, Mel’nichenko, Vovk.     

4-Functionally Substituted 3-Heterylpyrazoles: XIV. <Emphasis Type="Italic">N</Emphasis>-Benzyl-<Emphasis Type="Italic">N</Emphasis>-[3-aryl(heteryl)-4-pyrazolylmethylene]amines and Their Derivatives

Reduction with sodium tetrahydridoborate of Schiff bases derived from 3-aryl(heteryl)pyrazole-4-carbaldehydes and benzylamines gave N-benzyl-N-[3-aryl(heteryl)-4-pyrazolylmethylene]amines which were acylated with benzoyl chloride and succinic and maleic anhydrides to obtain the corresponding amides. Treatment of the title compounds with phenyl isothiocyanate afforded substituted thioureas.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 98–103.Original Russian Text Copyright © 2005 by Bratenko, Panimarchuk, Chornous, Vovk.     

New derivatives of 3-aminoindole. Synthesis of 2-aryl(hetaryl)-3-(3,5-dimethyl-1-pyrazolyl)indoles

The interaction of arylhydrazines with ù-(3,5-dimethyl-1-pyrazolyl)acetophenones and acetyl(2-thiophene) leads to arylhydrazones, which are converted by Fischer cyclization into 2-aryl(thienyl)-3-(3,3-dimethyl-1-pyrazolyl)indoles with substituents in positions 1, 5, and 7.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1662–1669, November, 2004.     

Synthesis of 5-Aryl(heteryl)-1-hydroxyethyl-4-(furyl-2-carbonyl)-3-hydroxy-3-pyrroline-2-ones

5-Aryl(heteryl)-1-hydroxyethyl-4-(furyl-2-carbonyl)-3-hydroxy-3-pyrroline-2-ones were synthesized via reactions of methyl ester of furyl-2-carbonylpyruvic acid with a mixture of aromatic or heterocyclic aldehyde and ethanolamine in dioxane. Antibacterial and antifungal activities of the synthesized compounds was studied.     

5-(2-苯基-1,2,3-三唑基)-3-芳基吡唑啉衍生物的合成及其荧光性能

以2-苯基-1, 2, 3-三唑基-4-甲醛为原料, 与苯乙酮［或取代苯乙酮(1a~1d)］发生羟醛缩合, 生成相应的查尔酮(2a~2d), 再与不同的肼反应, 合成了12种新的5位含2-苯基-1, 2, 3-三唑基的吡唑啉衍生物3a~3d, 4a~4d, 5a~5d. 化合物的结构经元素分析、 IR光谱和1 H NMR谱确认, 并测定了化合物的荧光光谱. 结果显示所合成的目标化合物有荧光, 是一类新型的荧光化合物.     

4-Functionally Substituted 3-Hetarylpyrazoles: VI. 1,3-Diaryl-4-isocyanatopyrazoles

1,3-Diaryl-4-isocyanatopyrazoles were obtained by reaction of 1,3-diarylpyrazole-4-carboxylic acids with ethyl chloroformate and sodium azide or by reaction of 1,3-diarylpyrazole-4-carbonyl chloride with trimethylsilyl azide. The title compounds react with amines, hydrazine hydrate, alcohols, phenols, and monochloroacetic acid to afford 4-pyrazolyl-substituted ureas, semicarbazides, urethanes, and amides respectively.     

2-[3-Phenyl-5-(m-Chlorophenyl)-2-Pyrazolin-1-yl]-3-Methyl-4(3H)-Quinazolinone

There are two molecules in the asymmetric unit (I and II). The structure consists of a 2-pyrazoline ring and three aromatic rings two of which are free and the third one is condensed with a 3-methyl-4(3H)-pyrimidine ring (4(3H)-Quinazolinone). While the pyrazoline ring is in the distorted envelope conformation, the free aromatic rings are planar and the pyrimidine ring deviates from the planarity. The crystal structure is stabilized by C–HO inter and intramolecular bonds.     

Functionally Substituted 3-Heterylpyrazoles: X. Reaction of 3-Aryl-1-phenyl-4-pyrazolecarbonyl Isothiocyanates with 3-Amino-5-methylisoxazole

3-Aryl-1-phenyl-4-pyrazolecarbonyl isothiocyanates react with 3-amino-5-methylisoxazole to afford 3-aryl-N-(3-acetonyl-1,2,4-thiadizol-5-yl)-1-phenylpyrazole-4-carboxamides.     

Facile one pot multicomponent synthesis of novel 4-(benzofuran-2-yl)-2-(3-(aryl/heteryl)-5-(aryl/heteryl)-4,5-dihydro-1H-pyrazol-1yl)thiazole derivatives

An efficient base catalyzed one pot multicomponent reaction of aryl/hetryl chalcones, thiosemicarbazide and 1-(benzofuran-2-yl)-2-bromoethan-1-one was developed to synthesize the novel 4-(benzofuran-2-yl)-2-(3-(aryl/heteryl)-5-(aryl/heteryl)-4,5-dihydro-1H-pyrazol-1yl)thiazole derivatives.     

Synthesis and Crystal Structure of 2（1-Phenyl-3-methyl-5-chloro-1H-pyrazol-4-yl）-3-（1-naphthoylamido）-4-thiazolidinone

1INTRODUCTIONManypyrazolederivativeshavebeenreportedtoshowvariousbiologicalactivitiestobeusedasbactericide[1],fungicide[2],herbicide[3],insecticide[4]andvirucide[5]agents.Inaddition,4-thiazolidinoneplaysavitalroleowingtoitswiderangeofbiologi-calactivities…     

4-Functionally Substituted 3-heterylpyrazoles: XII. 4-Chlorothieno[2,3-c]pyrazole-5-carbonyl Chlorides

3-(4-Pyrazolyl)acrylic acids reacted with excess thionyl chloride in the presence of benzyltriethylammonium chloride affording 4-chlorothieno[2,3-c]pyrazole-5-carbonyl chlorides which were converted into the corresponding acids, esters, and amides.