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SYNTHESIS AND REACTION OF NEW PYRAZOLE DERIVATIVES

机译：新型吡唑衍生物的合成与反应

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N-(4-(2-phenyldiazenyl)-2,5-dihydro-3-hydroxy-1H-pyrazol-5-yl)-2 chloroacetamide 2 was obtained from reaction of 3-amino-5-hydroxy -4- phenylazo-1H-pyrazole 1 with chloroacetylchloride . Reaction of 2 with malononitrile and ammoniumisothiocyanate gave the corresponding 1-(4-(2-phenyldiazenyl)-5-hydroxy-1H-pyrazol-3-yl)-2-amino-4,5-dihydro-5-oxo-1H-pyrrol-3-carbonitrile 3 and 3-(2-phenyldiazenyl)-7-amino-2-hydroxy pyrazolo[1,5-a] pyrimidin-5(1H)-one 4. Thiation of 1 with P2S5 gave the corresponding 3-amino-5-mercapto-4-phenylazo-1H-pyrazole 5. The reaction of compound 5 with chloroaceticacid, ethylchloroacetate, tetrahydrofuran, 3-hydroxybenzaldhyde, phencylbromide and ninhydrine gave the corresponding 6,7,8,9,10,11,12,13 respectively, as mercapto, N-substituted. While, hydrazenolysis of7 inthe presence of hydrazine hydrate afforded 8 and cyclization of11 in the presence aglacial acid and sulfuric acid mixture afforded 12. 1-(4-(2-phenyldiazenyl)-5-mercapto-1H-pyrazol-3-yl)-3- phenylthiourea 14 was obtained from reaction of 5 with phenyl isothiocyanate. pyrazolothiadiazole 15 and pyrazolotriazole 16 were obtained by the reaction of 14 with bromine in different solvents. 3-amino-5-hydrazino-4-phenylazo-1H-pyrazole 17 was obtained from reaction 5 with hydrazine hydrate. Cyclization of compound 17 by reacting it with ethylacetoacetate, acetylacetone, phthalic anhydride and phencylbromide gave the corresponding N-pyrazolylpyrazole derivatives 18 & 19, pyrazol-2,3-dihydrophthalazine-1,4-dione 20 and pyrazolotriazine 21, respectively. Reaction of 17 with sodium nitrate in the presence acetic acid, ethyl pyruvate and carbon disulfide gave the corresponding pyrazolotetrazole 22, imidazolopyrazole 23 and pyrazolotriazole derivatives 26. hydrazenolysis of 17 in the presence of hydrazine hydrate afforded 24 and cyclization it in the presence aglacial acid and sulfuric acid mixture afforded 25.
机译：N-（4-（2-苯基二氮烯基）-2,5-二氢-3-羟基-1H-吡唑-5-基）-2氯乙酰胺2由3-氨基-5-羟基-4-苯基偶氮- 1H-吡唑1与氯乙酰氯。 2与丙二腈和异硫氰酸铵反应得到相应的1-（4-（2-苯基二氮烯基）-5-羟基-1H-吡唑-3-基）-2-氨基-4,5-二氢-5-氧代-1H-吡咯-3-腈3和3-（2-苯基二氮烯基）-7-氨基-2-羟基吡唑并[1,5-a]嘧啶5（1H）-14。1与P2S5的稠合得到相应的3-氨基-5-巯基-4-苯基偶氮-1H-吡唑5。化合物5与氯乙酸，氯乙酸乙酯，四氢呋喃，3-羟基苯甲醛，苯溴铵和茚三酮的反应得到相应的6,7,8,9,10,11,12 ，13分别作为巯基，被N-取代。同时，在水合肼存在下进行7的肼解得到8，在冰醋酸和硫酸混合物存在下进行11的环化得到12。1-（4-（2-苯基二氮烯基）-5-巯基-1H-吡唑-3-基）-由5与异硫氰酸苯基酯反应获得3-苯基硫脲14。吡唑并噻二唑15和吡唑并三唑16是由14与溴在不同溶剂中反应制得的。由反应5与水合肼制得3-氨基-5-肼基-4-苯基偶氮-1H-吡唑17。通过使化合物17与乙酰乙酸乙酯，乙酰丙酮，邻苯二甲酸酐和苯溴铵反应而环化，分别得到相应的N-吡唑基吡唑衍生物18和19，吡唑-2,3-二氢邻苯二甲酰-1,4-二酮20和吡唑并三嗪21。 17在乙酸，丙酮酸乙酯和二硫化碳存在下与硝酸钠反应，得到相应的吡唑并噻唑22，咪唑并吡唑23和吡唑并三唑衍生物26。在水合肼存在下的17肼解反应得到24，并在冰醋酸和水存在下环化。硫酸混合物得到25。

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