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首页> 外文期刊>Russian Chemical Bulletin >Reaction of thiosemicarbazide with N-cyanoguanidine:synthesis of 3,5-diamino-1-thiocarbamoyl- and 3,5-diamino-1-thiazoI-2-yl-1,2,4-triazoles
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Reaction of thiosemicarbazide with N-cyanoguanidine:synthesis of 3,5-diamino-1-thiocarbamoyl- and 3,5-diamino-1-thiazoI-2-yl-1,2,4-triazoles

机译:硫代氨基脲与N-氰基胍的反应:3,5-二氨基-1-硫代氨基甲酰基和3,5-二氨基-1-噻唑基-2-基-1,2,4-三唑的合成

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摘要

The reaction of thiosemicarbazide with N-cyanoguanidine in an acidic medium afforded 3,5-diamino-1-thiocarbamoyl-1,2,4-triazole,whose condensation with alpha-halo ketones gave 3,5-diamino-1-thiazol-2-yl-1,2,4-triazoles 7a-d.The latter were also prepared by the independent synthesis from 2-hydrazinothiazoles and N-cyanoguanidine.Acylation of compounds 7a,d under mild conditions and their condensation with aldehydes occur at the C(3')NH_2 group.The structure of aroyl derivative 11c was established by X-ray diffraction.Acylation of diaminothiazolyltriazole 7a in boiling Ac_2O afforded 3,5-diacetylamino-l-(4-phenylthiazol-2-yl)-1,2,4-triazole.Hydrogenation of arylidene derivatives 14b,c and aroyl derivative 11c gave the corresponding benzylaminotriazoles 15a,b.
机译:硫代氨基脲与N-氰基胍在酸性介质中反应,得到3,5-二氨基-1-硫代氨基甲酰基1,2,4-三唑,其与α-卤代酮缩合得到3,5-二氨基-1-噻唑-2 -yl-1,2,4-三唑7a-d。后者也由2-肼基噻唑和N-氰基胍独立合成制备。化合物7a,d在温和条件下酰化并在C处与醛缩合(3')NH_2基团。通过X射线衍射确定芳酰基衍生物11c的结构。在沸腾的Ac_2O中酰化二氨基噻唑基三唑7a,得到3,5-二乙酰氨基-1-(4-苯基噻唑-2-基)-1,2 ,亚芳基衍生物14b,c和芳酰基衍生物11c的加氢得到相应的苄基氨基三唑15a,b。

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