Synthesis Of Diheterocyclic Compounds On 1,3,4-Oxadiazole-2-thiones And 1,2,4-Triazole-5-thiones

Recently,fluorinated functional compounds have gained chemist's more and more attentions.During the design,chemical synthesis and filtering of pharmaceuticals,poly-fluorinated substituented into various positions of the heterocyclic compounds often leads to significant changes in biological activities obviously as compared to nonfluorinated analogs.It has been reported that 1,3,4-oxadiazole-2-thione and its derivatives have displayed a broad range of biological activity,such as antimicrobial,anti-inflammatory action,preventing of low blood sugar coma,anti-tumor,anti-HIV virus and so on.Another kind of heterocyclic compounds:1,2,4-triazole derivatives can also counteract blood pressure,regulate plant growth and cause vasodilation activity,and so on.A few papers have reported the reactivity of the hydrogen of NH group in heterocycle,especially Mannich base reaction,however,the same hydrogen substituted by perfluoroalkyl has been not reported in the literature.Most acylamide compounds have pharmacological activity and acylamino can lead to improve potency through combined with organism to hydrogen bond..Especially arylamide can obviously improve molecular biological activity.Based on these,Compound 3 was synthesized by reaction of acid chloride with amino acid ester in the presence of Et₃N and DMF.After several steps'synthesis, the 1,3,4-oxadiazole-2-thiones(3-5) and 1,2,4-triazole-5-thiones(2-8) are obtained. Combining the oxadiazole and triazole with good activities,two series of N-perfluoroalkylethyl-substituted 1,2,4-triazole-5-thiones(2-9a～2-9l)and 1,3,4-oxa diazole-2-thiones(3-6a～3-6l) are synthesized in the second and the third chapter of this paper,and their structures are confirmed by ¹H-NMR,¹⁹F-NMR,IR,mass spectra and elemental analysis.Diheterocyclic compound's synthesis and biological activity research is another important research direction of heterocyclic pesticides.A great many litertures have reported bis-heterocycles have favourable and broad—spectrum biological activity,such as regulation of plant growth,antimicrobial and weeding, insecticidal,anti-inflammatory,analgesic,anti-cardiovascular disease and so on.To achieve the active superimposition and develop newly heterocyclic compounds.with highly-efficient and broad-spectrum activity,we gather the different biological activity functional group in the identical molecule.In the basis of front work,the fourth chapter in this paper,the N-perfluoroary-4-phenyl 5-(p-indinophenyl) -1,2,4-triazole-5-thiones and N-perfluoroaryl-5-(p-indinophenyl)-1,3,4-oxadiazole-2-thiones are spliced in the manner of Sonogashira coupling,which are based on molecular design technologies,design and synthesize several new dual-heterocyclic compounds,whose structure are confirmed by ¹H NMR,¹⁹F NMR,IR,MS spectra and elemental analysis.