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Summary. Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of.
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Scheme Synthesis of 3,5-diaminooximinopyrazole. Shvekhgeimer and Ushakova [55] have reported the synthesis of 4-arylazo-3,5-diaminopyrazoles 73 starting from substituted sulfonamides Scheme Synthesis of 4-arylazo-3,5-diaminopyrazoles. Reaction of ketenes, particularly those with a cyano group at one end and a leaving group such as alkoxy, alkylthio or halogen at the other, with hydrazine and its derivatives has assumed great importance in the synthesis of 5-aminopyrazoles [56,57].

The advantage of this procedure resides in the frequent possibility of forecasting the structure of the reaction product. However, Elnagdi et al. Scheme Synthesis of 3- or 5-aminocyanopyrazoles. These compounds were further treated with nitrous acid and coupled with different secondary amines to yield the triazenopyrazoles Scheme Synthesis of triazenopyrazoles. An interesting synthesis of 5 3 -aminopyrazoles 81 and 82 [63] has been developed using thioacetals 79 and 80 of malononitrile, which are conveniently obtained by the reaction of aniline and diethyl phosphite with bis methylthio methylenemalononitrile 74d , respectively.

Scheme Synthesis of 5 3 -aminopyrazoles. Scheme Synthesis of 3-substituted 5-aminocyanopyrazoles. Acylated hydrazine, as expected, reacts with ethoxymethylenemalononitrile 74a in a similar manner. Ketene dithioacetals 86 were utilized for the synthesis of corresponding pyrazole carbodithioates 88 by cyclization with methyl- or benzylhydrazine carbodithioate 87 in ethanolic TEA at room temperature.

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As before, the reaction proceeds via the nucleophilic substitution of the alkylthio group by the unsubstituted nitrogen of the hydrazine. Scheme Synthesis of 5-aminopyrazole carbodithioates and 5-aminoarylaminophenylpyrazolecarboxamides. Scheme Synthesis of 5-aminopyrazole carbodithioates and 5-aminoarylaminophenylpyrazolecarboxamide Scheme Synthesis of 5-aminocyanopyrazoles.

Scheme Synthesis of thiazolylpyrazoles. Nilov et al. Scheme Synthesis of 5-aminomethylpyrazolecarboxamide. These methods are summarized below.

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Synthesis of 4-acylamino-3 5 -amino-5 3 -arylsulfanylpyrazoles by the reaction of 2-acylaminoarylsulfanylchloroacrylonitriles with hydrazine hydrate has been described. Scheme Synthesis of 4-acylamino-3 5 -amino-5 3 -arylsulfanylpyrazoles. Scheme Synthesis of 5-aminoaryldiethoxyphosphorylhalomethylpyrazoles.

Heterocyclization reactions of trifluoromethylcyanovinyl phosphonates TFMCPs with arylhydrazines have been studied: TFMCPs can be used as precursors of 2,3-dihydro-1 H -pyrazoles modified by both trifluoromethyl and diethoxyphosphoryl groups. Further, the reaction of isomeric alkene with an arylhydrazine initially forms the unstable pyrazoline that transforms into pyrazole Scheme Synthesis of substituted 5-aminotrifluoromethylpyrazoles and Dodd et al.

Scheme Solid-support synthesis of 5- N -alkylamino and 5- N -arylaminopyrazoles. Scheme Synthesis of 5-aminocyanoacetylphenyl-1 H -pyrazole. Scheme Synthesis of 3-substituted 5-aminoaryl benzothiazolyl pyrazoles. Scheme Synthesis of 5-aminocarbethoxymethyl 4-sulfamoylphenyl pyrazole. Scheme Synthesis of inhibitors of hspphosphorylation and TNFa-release. The potassium salt of ethyl cyanopyruvate on reaction with methyl carbazate in a mixture of chloroform and ethyl acetate, saturated with hydrogen chloride resulted in situ protonation of the potassium salt followed by formation of intermediate hydrazone.

Further treatment with TEA in acetonitrile resulted in cyclization and furnished the new 5-aminopyrazole acid ester Reaction of with the acid chloride of 9-fluoroenylmethyl carbamate Fmoc -protected glycine led to peptide coupling and subsequent Fmoc deprotection with piperidine gave Scheme Synthesis of the diglycylpyrazole Scheme Synthesis of 5-aminoarylbenzoylpyrazole derivatives. The enamine nitrile reacts readily with 3-hydrazinopropanenitrile to yield via elimination of chloroform by the attack of less hindered nitrogen of reagent.

Scheme Synthesis of 4-benzoyl-3,5-diamino 2-cyanoethyl pyrazole. Treatment of with phenyl isothiocyanate in DMF in the presence of potassium hydroxide at room temperature, followed by treatment with methyl iodide afforded the novel ketene N , S -acetal Reaction of with hydrazine in refluxing ethanol gave the corresponding 5-aminopyrazole derivative The reaction proceeds in the usual manner, i. Scheme Synthesis of the 5-aminopyrazole derivative Hutaud et al.

Scheme Synthesis of 3,5-diaminopyrazoles Beam et al. Scheme Synthesis of 5-aminopyrazoles derivatives via lithiated intermediates. Scheme Synthesis of 5-amino 1,2,4-oxadiazolyl -pyrazoles The reaction of 3-aminothioacrylamide with hydrazine hydrochloride has been reported to furnish the 5-aminopyrazole in good yield. Scheme Synthesis of a 5-aminopyrazole with anticonvulsant activity. Another interesting synthesis that affords tetrasubstituted 5-aminopyrazole derivatives involves the reaction of N , N -disubstituted hydrazines with ketones [88].

Scheme Synthesis of tetrasubstituted 5-aminopyrazole derivatives. Abdelhamid et al. Scheme Synthesis of substituted 5-aminopyrazoles from hydrazonoyl halides. Ioannidou and Koutentis [91] investigated the conversion of isothiazoles into pyrazoles on treatment with hydrazine. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation were investigated. When a good nucleofugal group e. However, when the 3-substituent is not a good leaving group it is retained in the pyrazole product However, when the substituent at C-5 in isothiazole was a better nucleofuge e.

Several isothiazoles with a variety of C-4 substituents were also reacted with anhydrous hydrazine to yield the corresponding 3-aminophenylpyrazoles Scheme Synthesis of 3-aminophenylpyrazoles from isothiazoles. The reaction of hydroxylamine with 3- 4-phenyl-1,2,4-triazolyl chromones has been reported to give the 2-aminochromones Scheme Synthesis of 5-aminopyrazoles via ring transformation.

This review describes new strategies and the development of novel concepts along with conventional methods to synthesize a wide variety of substituted 5-aminopyrazoles.

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Jump to Scheme 5. Jump to Scheme 6. Jump to Scheme 7. Jump to Scheme 8. Jump to Scheme 9. Jump to Scheme WO A1 , Nov 30, Heterocycles , 78, — World-renowned chemists have chosen the most important molecular transformations and evaluated them. Over 2, scientists from 46 countries are part of our author community.

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