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1.
The reaction of 3-mercapto-4-arylideneamino-1,2,4-triazoles 2b-d , 3a-d with ethyl bromoacetate and/or phenacyl bromide in hot DMF and triethylamine affords the stereochemically pure 7-acyl-6-aryl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines 4b-d , 5a-d , 6b , d in which the consecutive hydrogen atoms N(5)H-C(6)H-C(7)H are cis to each other. This stereochemistry was determined by 1H NMR spectroscopy and confirmed by comparison with the spectrum of 3,6-diphenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine 10 . The latter was prepared by NaBH4 reduction of 3,6-diphenyl-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine 9 . The reported reactions offer two interesting stereospecific syntheses of the condensed heterocyclic compounds. 相似文献
2.
ZOU Kai-huang ZHANG Li-xue ** ZHANG An-jiang LEI Xin-xiang HUANG Hui-hua ZHANG Zi-yi . School of Chemistry Materials Science Wenzhou Normal College Wenzhou P. R. China . Department of Biology Chemistry Fujian Educational College Fuzhou P. R. China . College of Chemistry Chemical Engineering Lanzhou University Lanzhou P. R. China 《高等学校化学研究》2005,21(1):69-72
Introduction3,6- Disubstituted- 7H- 1 ,2 ,4- triazolo[3,4- b][1 ,3,4]thiadiazines are amongst the various hete-rocycles that received considerable attention duringthe last two decades as potential biologically activeagents.This kind of N- bridged heterocycles hasbeen reported to possess the wide spectrum of bio-logical properties,such as antimicrobial[1] ,an-tibacterial,antifungal[2 ] ,antiinflammatory[3 ] ,di-uretic[4] ,anthelmintic,and analgesic properties[5] .They can be also used as plant… 相似文献
3.
G. Mekuskiene M. M. Burbuliene V. Jakubkiene E. Udrenaite P. Gaidelis P. Vainilavicius 《Chemistry of Heterocyclic Compounds》2003,39(10):1364-1368
5-(4,6-Diphenyl-2-pyrimidinyl)-1,3,4-oxadiazole-2-thione reacted with haloalkanes or their derivatives containing side chain oxo group to give S-alkylated compounds. Aminomethylation and acylation of the thione yielded N(3)-derivatives. Treatment of the title compound with hydrazine hydrate in butanol resulted in 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-1,2,4-triazole-3-thione via a recyclization reaction. Reaction of the title compound with hydrazine hydrate or phenylhydrazine in dioxane led to formation of the corresponding thiocarbohydrazides. The latter in the presence of a base were cyclized to 4-amino-1,2,4-triazole-3-thiones. 相似文献
4.
1-苯基-3-甲基-5-氯-4-吡唑甲醛与4-氨基-5-取代苯基-1,2,4-三唑-3-硫酮缩合生成4-(1-苯基-3-甲基-5-氯吡唑次甲亚胺基)-5-(取代苯基)-2H-1,2,4-三唑-3(4H)-硫酮,再烷基加成化为新型含吡唑基5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物。 化合物结构经1H NMR、IR以及元素分析确认。 初步生物活性测试结果表明,在100 mg/L浓度下,化合物8a(3-(2-甲基苯基)-6-(5-氯-2-甲基-4-苯基吡唑)-7-(4-硝基苯基)-5H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪)对黄瓜炭疽病的抑制率达90%。 相似文献
5.
Five 5-substituted-4-(arylidene)amino-2,4-dihydro-3H-1, 2,4-triazole-3-thiones (2a-2e) and seven 6-aryl-3-(D-gluco-pentitol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines (3a-3g) were synthesized. The complete 1H and 13C NMR chemical shift assignments were analyzed on one- and two-dimensional NMR techniques, including DEPT, NOE-DIF, COSY, gHMBC, and gHSQC. 相似文献
6.
以4-氨基-5-苯氧甲基-3-巯基-1,2,4-三唑与取代苯氧乙酸为原料,三氯氧磷为溶剂,回流反应, 合成了3,6-二苯氧甲基-1,2,4-三唑并[3,4-b]-1,3,4-噻二唑衍生物。通过IR、1H NMR和元素分析确定了各化合物分子结构,并对其进行了室内毒力测试,结果表明此类化合物具有较好的杀菌、抑菌活性。 相似文献
7.
The interaction of 4-allyl-5-phenyl-1,2,4-triazole-3-thione with iodine proceeds with the formation of a mixture of 6-iodomethyl-3-phenyl-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole and 6-iodo-3-phenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b]-1,3-thiazine. The structures of the cyclization products obtained were established on the basis of the 1H NMR spectra of their dehydroiodinated derivatives. 6-Methyl-3-phenylthiazolo[2,3-c]-1,2,4-triazole, 3-phenyl-5H-1,2,4-triazolo[3,4-b]-1,3-thiazine, and 3-phenyl-7H-1,2,4-triazolo[3,4-b]-1,3-thiazine are formed on eliminating HI from the cyclization products. 相似文献
8.
Mamdouh A. M. Taha 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2525-2533
4-Amino-4H-3-methylthio{7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl}-1,2,4-triazole-5thi-ol (1) was condensed with various substituted aromatic aldehydes or acid chlorides to yield a series of arylideneamines 2 or aroylamines 3. These were easily cyclized to the corresponding 6-aryl-3-methylthio7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl-1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles (4) on treatment with palladium-on-charcoal or phosphorus oxychloride. Compounds 4 were also prepared directly via the reaction of 1 with aromatic carboxylic acids in the presence of phosphorus oxychloride. Cyclocondensation of 1 with a variety of two-carbon cyclizing reagents, namely chloroacetone, pyruvic acid, benzoylformic acid, and benzoin led to the formation of 3-methylthio{7H-1,2,4-triazolo[1,5-d]tetrazol-6-yl}-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (5?8). Some of the newly synthesized compounds were tested for their antibacterial and antifungal activity against a variety of microorganisms. 相似文献
9.
以对氟苯甲酰肼为初始原料,经成盐、环化和一锅法反应制得中间体5-对氟苯基-2,4-二氢-1,2,4-三唑-3-硫酮磷亚胺(4);4与芳基异氰酸酯发生氮杂Wittig反应,后经成环反应合成了11个新型的含氟6-芳氨基-1,2,4-三唑[3,4-b]-1,3,4-噻二唑衍生物(6a~6k),其结构经~1H NMR,~(13)C NMR,IR和HR-MS表征。对单、双子叶植物的除草活性测试结果表明:浓度为100 mg·L~(-1)时,6c和6f对稗草和萝卜的茎和根的生长表现出优异的抑制活性,抑制率高达100%。 相似文献
10.
The reaction of benzoyl isothiocyanates and methoxycarbonyl isothiocyanate with 4-amino-4,5-dihydro-3-(methylthio)-1,2,4-triazin-5-ones in acetonitrile gave several substituted 4H-1,3,4-thiadiazolo[2,3-c]-1,2,4-triazin-4-ones VIa-h instead of the expected thioureas. In addition, benzoyl isothiocyanate reacted with 4-amino-3-(methylthio)-5-(trifluoromethyl)-4H-1,2,4-triazole to give the benzoyl thiourea IX and with 4-amino-3-mercapto-5-(trifluoromethyl)-4H-1,2,4-triazole to give the bicyclic compound N-[3-(trifluoromethyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol-6-yl]benzamide IX . 相似文献
11.
取代苯甲醛与4-氨基-5-(3,4,5-三甲氧基苯基)-1,2,4-三唑-3-硫酮(2)缩合生成5-(3,4,5-三甲氧基苯基)-4-取代苯基亚胺基-1,2,4-三唑-3-硫酮(3),再烷基加成化为新型5,6-2H-1,2,4-三唑[3,4-b][1,3,4]噻二嗪衍生物4.化合物结构经1HNMR 13C NMR,IR以及元素分析确认.采用噻唑兰(MTT)比色法进行化合物抑制人体前列腺癌细胞(PC3)体外活性测试,结果表明所合成的化合物具有不同程度的抑制PC3活性,其中化合物4a在10μmol·L-1浓度下对PC3的抑制率为75.9%. 相似文献
12.
以4-氨基-5-(3,4,5-三甲氧基苯基)-3-巯基-1,2,4-三唑为原料,环化得到6-巯基-3-(3,4,5-三甲氧基苯基)-1,2,4-三唑[3,4-b][1,3,4]噻二唑再与取代苄氯反应,得到9个6-取代苄硫基-3-(3,4,5-三甲氧基苯基)-1,2,4-三唑[3,4-b][1,3,4]噻二唑类衍生物3a~3i.其结构经IR,1H NMR,MS和元素分析确证.初步生物活性测试结果表明部分化合物有一定的杀菌活性. 相似文献
13.
Bade Thirupaiah 《合成通讯》2014,44(4):513-519
A one-pot procedure has been developed for the synthesis of substituted 2,3-dihydro-2-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazin-3-yl)phthalazine-1,4-diones by reaction of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and phthalic anhydrides in acetic acid medium. Similarly, a one-pot, three-component synthetic procedure has been developed for substituted 3-[3-(N1-benzylidene-hydrazino)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-4-hydroxy-6-methyl-pyran-2-ones from 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and various aromatic aldehydes in absolute ethanol and a few drops of glacial acetic acid.
[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] 相似文献
14.
Condensation of 3-[(3-hydrazino-3-oxopropyl)anilino]-and 3-[(3-hydrazino-3-oxopropyl)-4-methylanilino]propane hydrazides with
2,4-pentanedione, phenyl isocyanate or phenyl isothiocyanate (with subsequent work up of the semicarbazides obtained by base),
and carbon disulfide gave respectively: 1-(3,5-dimethyl-1H-1-pyrazolyl)-3-[3-(3,5-dimethyl-1H-1-pyrazolyl)-3-oxopropylanilino]-1-propanone,
3-(2-{[2-(5-oxo-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethyl]anilino}ethyl)-4-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-one
and its thio analog, and 5-(2-{[2-(2-thioxo-2,3-dihydro-1,3,4-oxadiazol-5-yl)ethyl]anilino}ethyl)-2,3-dihydro-1,3,4-oxadiazole-2(3H)-thione
plus their methyl derivatives.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1353–1358, September, 2007. 相似文献
15.
Gundibasappa K. Nagaraja Vijayavittala P. Vaidya Koodamara Sheshappa Rai Kittappa M. Mahadevan 《Phosphorus, sulfur, and silicon and the related elements》2013,188(12):2797-2806
A novel and efficient method for the synthesis of substituted thiazepines and diazepines has been developed. A simple one-pot reaction of chalcones 1a–f with 1-amino-2-mercapto-5-phenyl-1,3,4-triazole and o-phenylenediamine in the presence of a catalytic amount of sodium acetate under microwave irradiation gave 2-(3,8-diphenyl-7,8-dihydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-6-yl)phenoles 2a–f and 2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenoles 3a–f, respectively. The structure of all the synthesized compounds was elucidated on the basis of elemental analysis, IR, 1H and 13C NMR, and mass spectral data. 相似文献
16.
Vijay V. Dabholkar Faisal Y. Ansari 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):298-305
Ultrasound accelerated synthesis of 2,3-(substituted)benzo-1,4-thiazino[5,6-b]-4H-9H-7- methyl-10-oxoquinolines (4), 7-substituted-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin- 4-one (5), 4-substituted-3,9, 10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-thiadiazino[2,3-d]- 1,2,4-triazole (6), and 7,7-dimethyl-7,8-dihydro-3H,5H,6H-1,2,4-triazolo[3,4-b][1,3,4] benzothiadiazin-9-one (7) from carbostyril and dimedone using sulfur powder and iodine as a catalyst in THF is reported. The structures of the compounds have been elucidated on the basis of spectral and elemental analysis. 相似文献
17.
N-(Furan-2-ylmethylidene)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-amine was prepared and alkyla- ted with the corresponding
halo compounds to afford N-alkylated products. 2-[3-(Furan-2-ylmethy- lideneamino)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-1-yl]acetohydrazide
was converted into the key intermediate thiosemicarbazide, which undergoes cyclization reactions under acidic and basic conditi-
ons to give 1,2,4-triazole, 1,3,4-oxadiazole, and 1,3,4-thiadiazole derivatives. Condensation of the hyd- razide with monosaccharide
aldoses gave the corresponding sugar hydrazones, which on treatment with acetic anhydride readily undergo cyclization reaction
to afford oxadiazoline derivatives. 相似文献
18.
M. A. Kukaniev M. M. Akbarova Z. G. Sangov S. S. Safarov D. M. Osimov 《Chemistry of Heterocyclic Compounds》2010,46(5):605-607
A one-reactor method has been developed for the synthesis of 3-methyl-6-R-6H-thiazolo[4,3-b]-1,2,4-triazolo[4,3-d]-1,3,4-thiadiazoles
by the condensation of aromatic aldehydes, thioglycolic acid, and 4-amino-5-methyl-1,2,4-triazole-3(2H)-thione in a sulfuric
acid medium. 相似文献
19.
研究了3-(2'-苯基-1', 2', 3'-连三唑-4'-基)-4-氨基-5-巯基-1, 2, 4-三唑(1)与取代苯甲酸和脂肪酸(2a-r)在POCl3催化下的反应, 共合成得到18个新的3-(2'-苯基-1', 2', 3'-连三唑-4'-基)-6-烷基/芳基-均三唑并[3, 4-b]-1, 3, 4-噻二唑(3a-r), 经元素分析,IR, 1H NMR和MS进行了结构确证。 相似文献