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首页> 外文期刊>Der Pharma Chemica: journal for medicinal chemistry, pharmaceutical chemistry and computational chemistry >Synthesis and reactions of oxadiazolo, thiadiazolo and triazolo phthalazin-1(2H)-one derivatives
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Synthesis and reactions of oxadiazolo, thiadiazolo and triazolo phthalazin-1(2H)-one derivatives

机译：恶二唑，噻二唑和三唑酞菁-1（2H）-一衍生物的合成与反应

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摘要

Reaction 2-{2,3-dichlorophenylcarbonyl}-benzoic acid 1 with hydroxylamine hydrochloride in boiling pyridine afforded 4-(2,3dichlorophenyl)-1H-2,3-benzoxazin-1-one 2 which on condensation with ethyl glycinate in the presence of sodium acetate gave ethyl[ 4-(2,3-dichlorophenyl)-1-oxophthalazin-2(1H)-yl)]acetate 3. The sulphonamide derivative 5 was prepared via the reaction of acid hydrazide 4 with p- toluene sulfonyl chloride in refluxing glacial acetic acid. Also, oxadiazole 6 was preformed through the reaction of the acid hydrazide 4 with ethyl chloroformate under reflux in nbutanol. N-amino 4-(2, 3-dichlorophenyl)-2-[5-oxo-4, 5-dihydro1, 3, 4-triazol-2-yl) methyl] phthalazin-1-(2H)-one 7 was prepared via condensation of oxadiazole 6 with hydrazine hydrate in boiling n-butanol. Thiadiazole drevative 10 was prepared by stirring the dithiacarbazate 8 with conc. H2SO4 at room temperature while on refluxing 8 in absolute ethanol afforded the oxadiazole 11. Each of 8, 10 and 11 on hydrazinolysis with hydrazine hydrate gave 2-(4-amino 5-thioxo-4, 5- dihydro-1H-1, 2, 4-triazol-3-yl) 4-(2, 3 dichlorophenyl)-phthalazin-1-(2H)-one 12. Thiourea derivative 15 was prepared by the reaction of 12 phenyl isothiocyanate in refluxing DMF. The structure of all compounds was confirmed from their correct analytical and spectral data.
机译：将2- {2,3-二氯苯基羰基}-苯甲酸1与盐酸羟胺在沸腾的吡啶中反应，得到4-（2,3-二氯苯基）-1H-2,3-苯并恶嗪-1-酮2，其在存在下与甘氨酸乙酯缩合乙酸钠得到乙酸乙酯[4-（2,3-二氯苯基）-1-氧酞菁-2（1H）-基）]乙酸乙酯3。磺酰肼衍生物5是通过酰肼4与对甲苯磺酰氯反应制备的。在回流的冰醋酸中。同样，通过酰肼4与氯甲酸乙酯在正丁醇中的回流反应，制得恶二唑6。制备了N-氨基4-（2，3-二氯苯基）-2- [5-氧代-4，5-二氢1，3，4-三唑-2-基）甲基]酞嗪-1-（2H）-一7。通过使乙二唑6与水合肼在沸腾的正丁醇中缩合来实现。通过将二硫代氨基甲酸酯8与浓硫酸一起搅拌来制备噻二唑衍生物10。在室温下用硫酸使之在无水乙醇中回流8，得到恶二唑11。与水合肼进行肼解反应后，分别将8、10和11生成2-（4-氨基5-硫代-4,5-二氢-1H-1,2 ，4-三唑-3-基）4-（2，3-二氯苯基）-酞菁-1-（2H）-一12。硫脲衍生物15是通过使十二苯基异硫氰酸酯在回流的DMF中反应制备的。所有化合物的结构均由其正确的分析和光谱数据证实。

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