Synthesis and biological evaluation of novel 1,2,4-triazole containing 1,2,3-thiadiazole derivatives

A series of novel 1,2,4-triazoles containing 1,2,3-thiadiazole derivatives were designed and synthesized. Their structures were confirmed by melting points, IR, 1H NMR, and elemental analysis and ESI-MS or HRMS. Preliminary bioassays indicated that these compounds exhibited very good insecticidal activity against Aphis laburni at 100 μg/mL, with mortality no less than 95%. Compounds 6a, 6c, 6f, 61 showed higher curative activity against TMV and compound 6h showed a higher induction effects against TMV in vivo at 100 μg/mL. Collectively, our data demonstrate a new strategy for control of insects and viruses.     

Synthesis of N-Vinyl-1,2,3-triazole Derivatives

Nitro-substituted N-vinyl-1,2,3-triazole derivatives were synthesized by the vinyl exchange reaction. The process was promoted by the catalytic system mercury(II) acetate-trifluoroacetic acid. This system is universal, and it can be used in the synthesis of vinylazoles having two, three, and four nitrogen atoms in the ring. in the ring.     

Synthesis and in-vitro antioxidant activities of some coumarin derivatives containing 1,2,3-triazole ring

A new green protocol was developed for the S-alkylation of 2-mercapto-1,3,4-oxadiazole by the reaction of 5-substituted-2-mercapto-1,3,4-oxadiazole with propargyl bromide in sodium bicarbonate in water. The newly synthesized 5-[(substitutedphenoxy)methyl]-2-[(prop-2-yn-1-yl)sulfanyl]-1,3,4-oxadiazole when reacted with azidomethyl coumarins underwent regioselective reaction yielding 4-(((4-((5-((substitutedphenoxy)methyl)-1,3,4-oxadiazol-2-yl)sulfanylmethyl)-1H-1,2,3-triazol-1-yl)methyl)-6-methyl)-2H-chromene-2-one or 1-((4-((5-((substitutedphenoxy)methyl)-1,3,4-oxadiazol-2-yl)sulfanylmethy)-1H-1,2,3-triazol-1-yl-)methyl)-3H-benzo[f]chromene-3-one. Structures of the newly synthesized compounds were confirmed by spectral and analytical data. The compounds were screened for their in-vitro antioxidant property.     

1,4-二取代-1,2,3-三唑衍生物的合成

在超声波辐射下,端基炔与叠氮基(3,3-二甲基-2,4-二氧戊环基)甲烷通过1,3-偶极环加成合成了1-(3,3-二甲基-2,4-二氧戊环基甲基)-4-芳基-1,2,3-三唑(5);5在酸性条件下脱保护得1-(2,3-二羟基丙基)-4-芳基-1,2,3-三唑,其结构经1H NMR,13C NMR,MS和元素分析表征。     

Synthesis of new pyrazole-1,2,3-triazole dyads

An efficient two step synthetic methodology of new 5(4)-aryl-4(5)-[3(5)-(2-hydroxyphenyl)-1H-pyrazol-5(3)-yl]-1H-1,2,3-triazole dyads was established. The reaction of (E)-2-styryl-4H-chromen-4-ones, used as building blocks, with sodium azide, gave 4(5)-aryl-5(4)-(chromon-2-yl)-1H-1,2,3-triazoles bearing either electron-donating or electron-withdrawing substituents in their styryl moiety which upon reaction with hydrazine hydrate afforded the expected pyrazoles in moderate to very good yields.     

Synthesis and biological activities of dithiocarbamates containing1,2,3-triazoles group

Twelve novel dithiocarbamates containing 1,2,3-trizaoles group were prepared via one step starting from organic halides, dithiocarbamic acid prop-2-ynyl ester, and sodium azide, using a very simple catalytic system composed of copper（I） chloride and water at 70 8C. The structures of the new compounds were characterized and screened for their in vitro anti-tumor. Four of the compounds displayed varying levels of anti-tumor activity against the CDC25 B.     

4-甲基-5-硝基-1,2,3-连三唑的合成

以丙二酸二乙酯为原料,经水解、硝化得到关键中间体偕二硝基乙酸乙酯(2);2与乙醛、叠氮化钠缩合环化得到4-甲基-5-硝基-1,2,3-连三唑(3)。3的结构经NMR,IR和元素分析表征。初步探讨了硝化反应的反应历程,并对制备2的合成进行了工艺改进,发现以NaNO2-98%HNO3为硝化试剂的新方法,2的收率达62.1%,纯度93.1%。     

Synthesis and fluorescence properties of nicotinonitrile 1,2,3-triazole derivatives

Russian Chemical Bulletin - A three-component condensation of 1,2,3-triazole chalcones, malononitrile, and sodium alkoxides afforded 6- and 4-(1,2,3-triazol-4-yl)substituted nicotinonitriles in...     

Synthesis and physical properties of high birefringence phenylacetylene liquid crystals containing a cyclohexyl group

We have synthesized new phenylacetylene-based liquid crystals containing a cyclohexyl or cyclohexylethyl group and evaluated their physical properties in order to develop a range of materials having high value of birefringence. The cyclohexyl-containing compounds exhibited nematic behaviour near room temperature and moderate values of δn of around 0.3. The cyclohexylethyl-containing compounds had a very wide nematic range with a high T_NI and very high values of δn of over 0.4. They also exhibited low viscosities. The order parameter was not affected by introducing either a cyclohexyl or a cyclohexylethyl group and the values of δn based on calculated polarizabilities were obtained experimentally.     

Synthesis and characterizations of 1,2,3-triazole containing polymers via reversible addition-fragmentation chain transfer (RAFT) polymerization

A novel monomer containing triazole and naphthalene ring, 2-(1-naphthalen-1-ylmethyl-1H-[1,2,3]triazol-4-yl)-ethyl methacrylate (NTEMA), was designed and synthesized via “click” chemistry method. The RAFT polymerization of NTEMA was successfully carried out using 2-cyanoprop-2-yl dithiobenzoate (CPDB) as a RAFT agent, 2,2′-azobisisobutyronitrile (AIBN) as an initiator in tetrahydrofuran (THF) solution. The results showed that the polymerizations exhibited “living”/controlled characteristics. The obtained poly(2-(1-naphthalen-1-ylmethyl-1H-[1,2,3]triazol-4-yl)-ethyl methacrylate) homopolymers, PNTEMAs, were further coordinated with samarium ion to prepare rare earth containing polymers (PNTEMA-Sm(III) complexes) which were characterized by FT-IR, DSC and ICP-AES. The characterization data confirmed that triazole in side chain of the polymer could coordinate with Sm(III). The fluorescence property of the polymers and polymer Sm(III) complexes were investigated in solution and in film.     

Synthesis of 1,2,3-triazole nucleosides via the acid-catalyzed fusion procedure

The acid-catalyzed fusion of methyl 1,2,3-triazole-4-carboxylate, 4-cyano-1,2,3-triazole, and 4-nitro-1,2,3-triazole with an acylated ribofuranose provided the corresponding 2-β-D-ribo-furanosyl-4-substituted-1,2,3-triazoles along with the isomeric 1-β-D-ribofuranosyl-4-substituted-1,2,3-triazoles. The structures of these nucleosides were assigned on the basis of their nmr spectra. The synthesis of 2-β-D-ribofuranosyl-1,2,3-triazole-4-carboxamide from both the corresponding methyl ester and cyano nucleosides is described. The cyano nucleosides were utilized to prepare 2-β-D-ribofuranosyl-1,2,3-triazole-4-thiocarboxa?ide and 1-β-D-ribofuranosyl-1,2,3-triazole-4-thiocarboxamide. Reduction of the 4-nitro-1,2,3-triazole nucleosides provided 4-amino-2-β-D-ribofuranosyl-1,2,3-triazole and the isomeric 4-amino-1-β-D-ribofuranosyl-1,2,3-triazole. The acid-catalyzed fusion procedure with 1,2,3-triazole afforded 1-β-D-ribofuranosyl-1,2,3-triazole and 2-β-D-ribofuranosyl-1,2,3-triazole.     

Anion-binding properties of a cyclic pseudohexapeptide containing 1,5-disubstituted 1,2,3-triazole subunits

A C(3) symmetric cyclic pseudohexapeptide containing 2-aminopicoline-derived subunits and 1,5-disubstituted 1,2,3-triazole rings is introduced as a potent anion receptor. This macrocycle was designed to mimic both the conformation and the receptor properties of a previously described cyclic hexapeptide containing alternating L-proline and 6-aminopicolinic acid subunits. Conformational analyses demonstrate that the cyclic peptide and the cyclic pseudopeptide are structurally closely related. Most importantly, both exhibit a converging arrangement of the NH groups, hence a good preorganization for anion binding. As a consequence, the pseudopeptide also very efficiently interacts with halide and sulfate ions, and this is the case even in competitive aqueous solvent mixtures. However, there are clear differences in the structures of both compounds, which translate into characteristic differences in receptor properties. Specifically, (i) the pseudopeptide possesses an anion affinity intrinsically higher than that of the cyclopeptide, (ii) the pseudopeptide is well preorganized for anion binding in a wider range of solvents from aprotic to protic, (iii) anion affinity in aprotic solvents is very high and associated with complexation equilibria that are slow on the NMR time-scale, (iv) the propensity of the pseudopeptide to form sandwich-type 2:1 complexes with two receptor molecules surrounding one anion is significantly lower than that of the cyclopeptide. A solvent-dependent calorimetric characterization of the binding equilibria of both compounds provided clear evidence for the stabilizing effect of hydrophobic interactions between the receptor subunits in such 2:1 complexes. The pseudopeptide thus represents the first member of a new family of anion receptors whose properties may be fine-tuned by varying the side chains in the periphery of the cavity.     

Synthesis of 1,2,3,4-tetrazine 1,3-dioxides annulated with 1,2,3-triazoles and 1,2,3-triazole 1-oxides

1,2,3,4-Tetrazine 1,3-dioxides annulated with 1,2,3-triazoles and 1,2,3-triazole 1-oxides have been synthesized by the reaction of 4-amino-5-(tert-butyl-NNO-azoxy)-2-R-2H-1,2,3-triazoles (R=Me, i-Pr, t-Bu) and their 1-oxides (R=H, Me, Et, i-Pr) with the HNO₃/H₂SO₄/Ac₂O system. Their thermal stability, spectroscopic, and X-ray properties have been studied.     

三氮唑偶联的阿拉伯糖苷化白杨素衍生物的合成与表征

利用点击化学,由三乙酰阿拉伯糖叠氮化物和炔丙基取代白杨素分子通过Cu催化的1,3-环加成反应得到了一种三氮唑阿拉伯糖苷化白杨素衍生物,利用核磁共振光谱、红外光谱、电子轰击质谱对其结构进行了表征,并利用元素分析测定了其组成.结果表明,所得合成产物为目标化合物.     

哌啶链接1,2,3-三氮唑化合物的合成及抗细菌活性

以丙二酸环异丙酯为起始原料,通过酯化生成甲酰乙酸叔丁酯衍生物(2a-2e);2再与4-叠氮基-1-Boc基哌啶在碳酸钾催化下经点击反应生成Boc-哌啶链接1,2,3-三氮唑衍生物(3a-3e);3在三氟乙酸作用下脱Boc基团,生成一系列新型哌啶链接1,2,3-三氮唑化合物(4a-4e)。所得到的5种化合物均未有文献报道,结构通过1H NMR,ESI-MS和元素分析进行表征。生物活性测试结果表明,五种化合物均有良好的抗细菌活性。