• 제목/요약/키워드: 1,2,3-Triazole

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Theroetical Study of the Nonlinear Optical Properties of Thiophene, Furan, Pyrrole, (1,2,4-triazole), (1,3,4-oxadiazole), and (1,3,4-thiadiazole) Monomers and Oligomers

  • 최우성;김태원;정승우;김철주
    • Bulletin of the Korean Chemical Society
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    • 제19권3호
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    • pp.299-307
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    • 1998
  • PM3 semiempirical calculations were carried out to study the frequency-dependent nonlinear optical properties of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-oxadiazole, and (1,3,4)-thiadiazole monomers and oligomers. The longitudinal component, αxx, is the largest of three principle components. On the other hand, the out-of-plane component, αzz, is the smallest. Moreover, the out-of-plane component (αzz) of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-oxadiazole, and (1,3,4)-thiadiazole monomers show constant changes with increasing optical frequencies. The frequency-dependent first- order polarizabilities increase in the order: thiophene > (1,2,4)-triazole > pyrrole > furan > (1,3,4)-thiadiazole > (1,3,4)-oxa-diazole monomers and oligomers. The effects of β(-2ω;ω,ω) (SHG) shows a larger dispersion compared with (-ω;ω,0) (EOPE) and β(0;-ω,ω) (OR). The second- order polarizabilities of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-thiadiazole, and (1,3,4)-oxadiazole monomers for the various second- order effects have the order: β(-2ω;ω,ω) (SHG) > β(-ω;ω,0) (EOPE) > β(0;-ω,ω) (OR) and thiophene > pyrrole > (1,2,4)-triazole > furan > 1,3,4-thiadiazole > 1,3,4-oxadiazole monomers. The third- order polarizabilities for the various third- order effects have the following order: γ(-3ω;ω',ω,ω) (THG) > γ(-2ω;0,ω,ω) (EFISHG) > γ(-ω;ω',-ω,ω) (IDRI) > γ(-ω;0,0,ω) (OKE). The effects of THG increase rapidly with increasing optical frequencies compared with the other effects. In particular, OKE effects increase most slowly with increasing optical frequencies. Also, the effects of THG for thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-thiadiazole, and (1,3,4)-oxadiazole oligomers show the order thiophene > (1,2,4)-triazole > furan > pyrrole > (1,3,4)-thiadiazole > (1,3,4)-oxadiazole oligomers. In particular, the third- order polarizabilities of thiophene and (1,3,4)-thiadiazole oligomers are about four and three times larger than those of (1,3,4)-oxadiazole and (1,2,4)-triazole oligomer, respectively.

Synthesis and $\beta$-lactamase inhibitory acitvity of 6-exomethylene penamsulfone derivatives -I (Synthesis of 1-substituted thioalkyl-l,2,3-triazole-4-carboxaldehyde)

  • Park, Hee-Suk;Oh, Jeong-Suk;Chaeuk Im;Yim, Chul-Bu
    • 한국응용약물학회:학술대회논문집
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    • 한국응용약물학회 1997년도 춘계학술대회
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    • pp.70-70
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    • 1997
  • $\beta$-Lactamase 억제제로 6-Substituted exomethylene기를 갖는 penam계 화합물이 강력한 활성을 보여주고 있어서, $\beta$-lactamase억제제의 중간체 합성으로 6-exomethylene기에 도입 할 1-substituted thioalkyl-1,2,3-triazole-4-carboxaldehyde를 합성하였다. 2-Bromoethanol에 NaN$_3$를 반응시켜서 2-Azidoethanol을 합성하였고, 이것을 propargyl aldehyde와 반응시켜서 1-(2-hydroxyethyl)-1,2,3-triazole-4-carboxaldehyde를 합성하였다. 이것을 trifluoromethanesulfonic anhydride와 triethylamine존재 하에 heterocyclic mercapto화합물과 반응시켜서 hetorocyclic ring을 함유한 1-substituted thioalkyl-1,2,3-triazole-4-carboxaldehyde를 합성하였다.

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New Thiazolo[3,2-b][1,2,4]triazole Derivatives : Useful Compounds for the Preparation of 7-Substituted Cephalosporins

  • Nam, Ghil-Soo;Lee, Jae-Chul;Chi, Dae-Yoon;Kim, Joong-Hyup
    • Bulletin of the Korean Chemical Society
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    • 제11권5호
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    • pp.383-386
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    • 1990
  • We have synthesized several bicyclic heteroaromatic compounds with bridgehead nitrogen from N-amine salts of heteroaromatic amines. 2-Amino and 2-unsubstituted thiazolo[3,2-b][l,2,4]triazole derivatives 2a-b were prepared by the cyclization reaction from N-amine salts of aminothiazole-5-yl(N-methoxyimino)acetate with cyanogen bromide and formamidine acetic acid salt, respectively. 2-Methylthiazolo[3,2-b][1,2,4]triazole 2c was obtained from N-acetylated N-amine salt of aminothiazole-5-yl(N-methoxyimino)acetate by the cyclization reaction in the presence of polyphosphoric acid (PPA). 2-Substituted and 2-unsubstituted thiazole[3,2-b][1,2,4]triazole derivatives 2a-c were coupled with 7-aminocephalosporanic acid (7-ACA). Coupled cephalosporin derivatives 1a-c did not have good antibacterial activities in vitro.

5-Phenyl-tetrazole의 光分解反應과 그 메카니즘에 관한 硏究 (The Mechanism in the Photolysis of 5-Phenyl-tetrazole Derivatives)

  • 채영복;장경수;김성수
    • 대한화학회지
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    • 제11권3호
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    • pp.85-88
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    • 1967
  • 5-Phenyl-tetrazole은 光分解하면 질소 한 分子를 放出하며 1,3-dipole인 C-phenyl-nitrilei-mine을 形成한다. 그러나 이때 dipolarphile의 存在下에서 1,3-dipole-cyclo-addition은 일으키지 않으며 二重合體인 3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine(III)을 거쳐 最終産物로서 3,6-diphenyl-1,2,4,5-tetrazine(IV), 2,5-diphenyl-1,2,4-triazole, 4-amino-3,5-diphenyl-1,2,4-triazole, benzonitrile, ammonia 그리고 nitrogen을 生成한다.

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Reactions with Heterocyclic Amidines (V). Synthesis of some new imidazo[l, 2-b] pyrazole,pyrazolo[5,1-C]-1,2,4-triazine and pyrazolo [5, 1-c]-1,2,4-triazole derivatives

  • Ali Elagamey, Abdel Ghani;Ahmed Sowellim, Salah Zaki;Mohamed Nabil, Khodeir
    • Archives of Pharmacal Research
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    • 제10권1호
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    • pp.14-17
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    • 1987
  • Several new imidazo [1, 2-b] pyrazole, pyrazolo [5, 1-c]-1, 2, 4-triazine and pyrazolo [5, 1-c] triazole derivatives were prepared from the reaction of 3-antipyrinyl-5-aminopyrazole or its diazonium salt with .alpha.-chloroacetyl derivatives.

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1,2,4-Triazole기를 가지고 있는 S-glycoside들의 합성 및 항균활성시험 (Synthesis and Antibacterial Activities of New S-glycosides Bearing 1,2,4-Triazole)

  • Chao, Shu-Jun;Geng, Ming-Jiang;Wang, Ying-Ling
    • 대한화학회지
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    • 제54권6호
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    • pp.731-736
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    • 2010
  • 5-Aryl-3-($\beta$-D-glucopyranosylthio)-1,2,4-triazole 화합물들을 합성하였으며, 합성한 화합물들에 대한 항균활성시험을 수행하였다.

1,2,4-Triazine III : 1,2,4-Triazine 유도체의 Methiodide 염 합성과 이들 염의 고리 축소화반응에 의한 1,2,4-Triazole 유도체 합성 (1,2,4-Triazine III : Synthesis of 1-Methyl-1,2,4-triazinium Iodides and Their Ring Contraction Reaction to 1-Methyl-1,2,4-triazoles)

  • 이재근;유향선
    • 대한화학회지
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    • 제33권4호
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    • pp.419-425
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    • 1989
  • 1,2,4-Triazine 유도체들을 acetone 용매하에서 methyl iodide와 반응시켜 다양한 1-methyl-1,2,4-triazinium iodide 염을 합성하였다. 또한 이들 염을 10% NaOH 수용액 내에서 $K_3Fe(CN)_6$로 산화시킨 결과 고리 축소화반응이 일어나 1-methyl-1,2,4-triazole 유도체를 주로 얻을 수 있었으나 $C_6$에 치환기가 없을 경우는 미량이긴 하지만 1,6-dihydro-6-oxo-1,2,4-triazine 유도체도 동시에 얻을 수 있었다. 고리 축소화반응은 $OH^-$에 의해 먼저 pseudo base를 형성하고 이 Pseudo base가 1-methyl-1,2,4-triazole과 1,6-dihydro-6-oxo-1,2,4-triazine으로 진행됨을 확인할 수 있었고 또한 1,2,4-triazine의 3개의 질소원자 중 $N_1$ 원자에 quaternization됨을 확인할 수 있었다.

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Synthesis of 8-Alkoxy-4,5-dihydro-[1,2,4]triazole[4,3-a]quinoline-1-ones and Evaluation of their Anticonvulsant Properties

  • Sun, Xian-Yu;Jin, Yun-Zhe;Li, Fu-Nan;Li, Gao;Chai, Kyu-Yun;Quan, Zhe-Shan
    • Archives of Pharmacal Research
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    • 제29권12호
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    • pp.1080-1085
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    • 2006
  • A series of 8-alkoxy-4,5-dihydro-[1,2,4]triazole[4,3-a]quinoline-1-one derivatives were synthesized using 7-hydroxy-3,4-dihydro-2(1H)-quinolone as the starting material. Their anticonvulsant activities were evaluated by the maximal electroshock test (MES) and the subcutaneous pentylenetetrazole test (sc-PTZ), and their neurotoxicities were measured by the rotarod neurotoxicity test (Tox). The tests demonstrated that 8-hexyloxy-4,5-dihydro-[1.2.4]triazole[4.3-a]quinoline-1-one (4e) and 8-heptyloxy-4,5-dihydro-[1,2,4]triazole[4, 3-a]quinoline-1-one (4f) were the most potent anticonvulsants, with 4e having $ED_{50}$ values of 17.17 mg/kg and 24.55 mg/kg and protective index ($PI=TD_{50}/ED_{50}$) values of 41.9 and 29.3 in the MES and sc-PTZ tests, respectively, and 4f having $ED_{50}$ values of 19.7 mg/kg and 21.2 mg/kg and PI values of 36.5 and 33.9 in the MES and sc-PTZ tests, respectively. The PI values of 4e and 4f were many fold better than that of the marketed drugs phenytoin, carbamazepine, phenobarbital and valproate, which have PI values in the range of 1.6-8.1 in the MES test and <0.22-5.2 in the sc-PTZ test. Structure-activity relationships were also discussed.

Syntheses, Structures, and Characterization of Two Novel Copper(II) and Cadmium(II) Compounds Based on Pyridyl Conjugated 1,2,3-Triazole

  • Hong, Jin-Long;Qu, Zhi-Rong;Ma, Hua-Jun;Wang, Gai-Gai;Zhao, Hong
    • Bulletin of the Korean Chemical Society
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    • 제35권5호
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    • pp.1495-1500
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    • 2014
  • Two new complexes with 5-methyl-1-(pyridine-3-yl)-1H-1,2,3-triazole-4-carboxylic acid (Hmptc) ligand: [$Cd(mptc)_2(H_2O)_4$] (1) and $[Cu(mptc)_4{\cdot}2H_2O]_n$ (2) were prepared and their crystal structures were determined by single crystal X-ray diffraction analyses. In complex 1, the Cd(II) ions coordinates with the pyridyl nitogen atom from the Hmptc ligand, forming a mononuclear Cd(II) compound. Complex 2 exhibits a novel two-dimensional (2D) polymer in which four Hmptc ligands stabilize the Cu(II) atom. And the coordination involves one nitrogen atom of the triazole, one oxygen atom of the carboxylic acid and the pyridyl nitrogen atom. In addition, FT-IR and solid-state fluorescent emission spectroscopy of two compounds have been determined.