Some 2-aryl-5-azaindandiones-1, 3

Condensation of cinchomeronic acid with p-nitrophenylacetic acid, of 2, 6-dimethylcinchomeronic acid with phenylacetic acid, and p-nitrophenylacetic acid in acetic anhydride solution in the presence of triethylamine followed by rearrangement of the condensation products with sodium methoxide gives 2-(p-nitrophenyl)-5-azaindandione-1, 3, 4, 6-dimethyl-2-phenyl-5-azaindandione-1, 3, and 4, 6-dimethyl-2-(p-nitrophenyl)-5-azaindandione-1, 3. Reaction of the alkali metal salts of these compounds with dimethyl sulfate leads to alkylation at the nitrogen atom, and formation of N-methyl betaines of the corresponding 5-azaindandiones. 2-Aryl-5-azaindandiones and their N-methyl betaines are dark in color (black to reddish brown), sparingly soluble, and decompose at 250-350°.     

Synthesis and properties of 5-aryl-3-diazo-3H-pyrazoles and 3-aryl-1H-pyrazole-5-diazonium salts. Preparation and cytolytic activity studies of 2-arylpyrazolo-[5,1-c][1,2,4]benzotriazines

Chemistry of Heterocyclic Compounds - A comparative analysis of physicochemical properties and reactivity of 3-aryl-1H-pyrazole-5-diazonium tetrafluoroborates and 5-aryl-3-diazo-3H-pyrazoles in azo...     

3-芳基-5-巯基-1,2,4-三唑的亲核取代反应研究

以3-芳基-5-巯基-1,2,4-三唑为原料合成了20个3-芳基-1,2,4-三唑-5-巯基乙酸乙酯(2a～e)、3-芳基-1,2,4-三唑-5-巯基乙酸(3a～e)、3-芳基-5,6-二氢噻唑并[2,3-c]均三唑(5a～e)和3-芳基-6,7-二氢均三唑并[3,4-b][1,3]噻嗪(6a～e)。研究了3a～e在微波辐射下的环化反应，合成了5个3-芳基-5-氧代-6H-噻唑[2,3-c]均三唑(4a～e)。产物经元素分析、红外、核磁共振以及质谱方法确定了结构。初步研究了代表化合物的生物活性。     

Investigations in the 4-aryl-5-arylamino-1,2,4-triazoline-3-thione series

Cyanoethylation of 4-aryl-5-arylamino-1,2,4-triazoline-3-thiones proceeds at the nitrogen atom of the thioamide group. Alkylation of 4-aryl-5-arylamino-1,2,3-triazoline-3-thiones with chloroacetonitrile, monochloroacetic acid and its ester, -chloropropionic acid, and methyl iodide proceeds at the sulfur atom. The acidity constants of substituted 4-phenyl-5-phenylamino-1,2,4-triazoline-3-thiones differ by two orders of magnitude from the acidity constants of the more acidic substituted 4-phenyl-1,2,4-triazoline-3-thiones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 129–132, January, 1971.     

Synthesis and transformations of 3-aryl-5-dichloromethyl-1H-1,2,4-triazoles

A method of synthesis of 3-aryl-5-dichloromethyl-1H-1,2,4-triazoles was developed, some chemical transformations of the synthesized compounds were performed, and dichloromethyl fragment in these compounds was shown to exhibit the characteristics of aldehyde group.     

Synthesis of 1-aryl-3-trifluoromethyl-5-methylthio-1,2,4-triazoles from 2-arylmethylisothiosemicarbazides and 1,1,1-trichloro-3,3,3-trifluoroacetone

The reaction of 1,1,1-trichloro-3,3,3-trifluoroacetone with S-methyl-2-arylisothiosemicarbazides affords an unusual synthesis of 1-aryl-3-trifluoromethyl-5-methylthio-1,2,4-triazoles from which 1-aryl-3-trifluoromethyl-1,2,4(4H)-triazole-5-ones are obtained on treatment with base.     

1-苯基-5-芳基-1,2-二氢-1,2,4-三唑-3-硫酮的合成

将取代苯甲酰氯1a～1f与硫氰酸钾反应, 得到的中间体不需纯化直接与苯肼反应, 成功地合成了1-苯基-5-芳 基-1,2-二氢-1,2,4-三唑-3-硫酮(2a～2f). 化合物2的结构通过红外光谱、核磁共振光谱和高分辨质谱进行了表征.     

The formation of 1,2,4-triazolylimidazolidine-2,4-diones in reactions of 3-aryl-1,2,4-triazin-5(2H)-ones with alkylureas

Recyclization of the addition products of alkylureas to 3-aryl-1,2,4-triazin-5(2H)-ones affording 1,2,4-triazole derivatives was found to occur in Ac₂O.     

Haloacetylated enol ethers. 7 . Synthesis of 3-aryl-5-trihalomethylisoxazoles and 3-aryl-5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles

β-Aryl-β-methoxyvinyl trihalomethyl ketones 1a-g, 2a-g [aryl = p-YC₆H₄ where Y= H, Me, OMe, F, Cl, Br, NO₂] are cyclocondensed with hydroxylamine hydrochloride to afford the 3-aryl-5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles 3a-g, 4a-f in good yield. The dehydratation of compounds 3a-g with concentrated sulfuric acid, led the corresponding 3-aryl-5-trichloromethylisoxazoles 5a-g . An alternative one-pot procedure yields 3-aryl-5-trihalomethylisoxazoles 5,6a-g directly by cyclocondesation of 1,2a-g with hydroxylamine hydrochloride in the presence of an excess of concentrated hydrochloric acid.     

3-（2-呋喃基）-4-芳基-1，2，4-三唑啉-5-硫酮的合成及生物活性

1-（2-呋喃甲酰基）-4-芳基氨基硫脲经过环化反应，制备了一系列新的化合 物3-（2-呋喃基）-4-芳基-1，2，4-三唑啉-5-硫酮类化合物，并通过元素分析和 IR，^1H NMR等波谱数据确证了上述化合物的结构。初步的生物活性实验表明其中 有些化合物的具有非常好的植物生长调节活性。     

Synthesis of 5-aryl-3-carbazoyl-1,3,4-oxadiazol-2(3H)-one. Derivatives and their ring transformation into 5-benzamido-1,2,4-triazolidine-3,5-dione derivatives

Some 5-aryl-3-carbazoyl-1,3,4-oxadiazol-2(3H)-one derivatives 6 and 9 have been synthesized in two ways. The expected thermal ring transformation into 2,5-disubstituted 1,3,4-oxadiazoles did not occur but, by acid hydrolysis of 5-aryl-3-[3-benzylidene-2-methyl(or phenyl)carbazoyl]-1,3,4-oxadiazol-2(3H)-ones 6 , a new ring transformation took place and the corresponding 4-benzamido-1-methyl(or phenyl)-1,2,4-triazolidine-3,5-dione derivatives 11 were formed. The 4-amino-1-phenyl-1,2,4-triazolidine-3,5-dione ( 19 ) has been prepared and its structure was confirmed by some reactions.     

35Cl Nuclear quadrupole resonance spectra of 3(5)-aryl-5 (3)-chloro-1,2,4-triazole

The ³⁵Cl nuclear quadrupole resonance (NQR) spectra of a number of 3(5)-aryl-5(3)-chloro-1,2,4-triazoles were studied. The energically most favorable tautomeric forms of the molecules were established, and a correlation between the ³⁵Cl NQR frequencies and the _m and ₀ reaction constants of the substituents in the aromatic ring was found.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 837–838, June, 1982.     

Environmentally friendly and efficient: iron-mediated reduction of 3-methyl-5-aryl-1,2,4-oxadiazoles to benzamidines

A new synthetic method is described for the mild and selective reduction of 3-methyl-5-aryl-1,2,4-oxadiazoles to amidines employing iron powder in aqueous medium. Its application is demonstrated in the synthesis of 1, a potent and selective urokinase-type plasminogen activator (uPA) inhibitor.     

Carbon-13 NMR Studies of 3-Aryl-4-(5-aryl-Δ 2-1,2,4-oxadiazolin-3-yl)sydnones and 3-Aryl-4-(5-aryl-1,2,4-oxadiazol-3-yl)sydnones

The ¹³C NMR spectra of twelve 3-aryl-4-(5-aryl-Δ²-l,2,4-oxadiazolin-3-yl)sydnones and twelve 3-aryl-4-(5-aryl-l,2,4-oxadiazol-3-yl)sydnones have been measured and assigned by means of proton-noise decoupling and DEPT-experiments. The coupling constants were determined by means of gated decoupling, and NOE effects were observed by comparison of proton-decoupled and inverse-gated decoupled spectra. Differences shown by the oxadiazoline and the oxadiazole rings and the substitution effects are discussed.     

Rapid acid hydrolysis of 5-aryl-3-(β-thiomorpholinoethyl)-1,2,4-oxadiazoles

The acid hydrolysis of a series of 5-aryl-3-(β-thiomorpholinoethyl)-1,2,4-oxadiazoles gave substituted benzoic acids and 2-amino-8-thia-1-aza-5-azoniaspiro[4.5]dec-1-ene chloride hydrate, whose structure was demonstrated by spectral methods and X-ray diffraction structural analysis.