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Likewise the 1,3,4-thiadiazole nucleus which incorporates an N-C-S linkage exhibits a large number of biological activities[1]. The fused 1,3,4-triazolo[3,4-b]-1,3,4-thiadiazoles derivatives show various biological effects, such as antifungal[2], antibacterial, hypotensive and CNS depressant activities[3]. The novel 3-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazole 6 have been synthesized by the condensation of 4-amino-5-mercapto-3-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-s-triazole 5 with formic acid in the presence of phosphorus oxychloride. The compound 5 was prepared from 4 that was prepared from 1 throng 2 and 3. Recently, we obtained the crystal structure of the novel compound 3-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazole, C14H12Cl3N7S, Mr=416.72, Crystallizes in the triclinic space group with unit cell parameters a=9.049(2), b=10.486(3), c=10.843(2)Å, α=116.79(2), β=93.83(2), γ-100.64(3)°. V=889.3(4)Å3, Z=1, Dx-0.778 Mgm-3. The final R was 0.0535. 相似文献
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以(S)-2-氨基丙醇和氯乙酰氯为起始原料,经酰化和环合反应制得(S)-5-甲基吗啉-3-酮(4); 4经还原制得(S)-3-甲基吗啉(5); 5与4-溴-2-甲基苯甲酸酰化缩合合成了(S)-(4-溴2-甲基苯基)(3-甲基吗啉)-甲酮,总收率57%,其结构经1H NMR 和 13C NMR确证。 相似文献
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The reaction of 4,4-dimethyl-3-oxobutanoic (or pentanoic) acid esters with the lactim ether of 2-pyrrolidone in the presence of 2-hydroxypyridine produces condensation products 4 in 57–72% yield. Acidic hydrolysis of 4 affords the furandione system 5 in 75–81% yield. 相似文献
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1,2,3-Triazole derivatives have been reported as inhibiting tumor proliferation, invasion, and metastasis[1]. The fused l,3,4-triazolo[3,4-b]-1,3,4-thiadiazoles derivatives show various biological effects such as antifungal[2], antibacterial, hypotensive and CNS depressant activities[3]. We have reported several 6-aryl-3-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazoles in the previous paper[4]. The novel 6-aryl-3-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-s-triazolo[2,4-b]-1,3,4-thiadiazoles 6a-j have been synthesized by the condensation of 4-amino-5-mercapto-3-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-s-triazole 5 with various aromatic carboxylic acids in the presence of phosphorus oxychloride. The mercaptotriazole 5 was prepared from 4,the latter being prepared from 1 throng 2 and 3. The title compounds 6 were depicted in scheme 1. The structures of these compounds were established by elemental analysis, NMR, MS and IR techniques. 相似文献
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V. A. Slavinskaya D. É. Sile M. Yu. Katkevich É. Kh. Korchagova N. G. Panchenko I. U. Lipsbergs E. Lukevics 《Chemistry of Heterocyclic Compounds》1998,34(1):35-39
The hydrogenation of 4-(2-furyl)-2-oxobutenoic acid sodium salt on a nickel catalyst has been studied. Using Raney nickel catalyst, the corresponding salts of 4-(2-furyl)-2-oxobutanoic acid, 4-(2-furtyl)-2-hydroxybutanoic acid, and aliphatic hydrogenolysis products of the initial compound were obtained. The sodium salt of 2-hydroxy-4-(2-tetrahydrofuryl) butanoic acid and the condensation product 4-(2-furylethyl)-3-(2-furylmethyl)-2-oxo-3,4-didehydroglutaric acid were detected in the hydrogenolysate. A method has been developed for obtaining the sodium salts of 4-(2-furyl)-2-oxobutanoic and 4-(2-furyl)-2-hydroxybutanoic acids.Latvian Institute of Organic Synthesis, Riga LV-1006, e-mail: elmira@osi.lanet.lv. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 41–45, January, 1998. 相似文献
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以对甲苯胺为原料,经重氮化、KI分解得到对-碘甲苯.在NH4Cl存在下,对-碘甲苯在过硫酸铵的氧化下与异丁苯反应,得到(4-甲苯基)(4-异丁基苯基)碘鎓氯.在丙酮溶剂中,(4-甲苯基)(4-异丁基苯基)碘鎓氯与六氟磷酸钾进行离子交换,得到目的产物(4-甲苯基)(4-异丁基苯基)碘鎓六氟磷酸盐.总收率为46.7%.通过紫外光谱、红外光谱和核磁共振测定,对产物进行了结构确证. 相似文献
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(Z)-3-丁烯基-4-羟基苯酞的合成李绍白,王志伟,方小平,李裕林(兰州大学应用有机化学国家重点实验室,兰州,730000)关键词(Z)-3-丁烯基-4-羟基苯酞,苯酞,3-丙基-5-羟基异香豆素,异香豆素,合成(Z)-3-丁烯基-4-羟基苯酞(1... 相似文献
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以N-吡啶基吡唑甲酸和2-氨基-3-甲基苯甲酸为起始原料,经由亲核加成、环化和酰化等多步反应合成了一系列结构新颖的N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)酰胺类化合物.测试了所合成化合物的杀虫及抑菌活性,结果表明,新化合物大多化合物在200 mg·L^-1浓度下对东方粘虫(Mythimna separataWalker)具有一定的杀虫活性,尤其是N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)乙酰胺(8a)和N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-3-氯-2,2-二甲基丙酰胺(8e)致死率可达70%;部分化合物在50 mg·L^-1浓度下对油菜菌核病菌的抑菌活性相对较好(54.5%~63.6%),优于triadimefon和chlorantraniliprole;部分化合物如N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-3,3-二甲基丁酰胺80和N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-4-氟苯甲酰胺(8h)对苹果轮纹病菌具有中等抑菌活性.值得注意的是,化合物8e的杀粘虫活性和对油菜菌核病菌的抑菌活性都较为突出,可用作新农药创制研究的新型参考结构. 相似文献
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以1-磺丁基-3-甲基咪唑硫酸氢盐离子液体(b)为反应介质,7-氨基头孢烷酸(7-ACA,2)为原料,与4-甲基-5-甲酰基噻唑经缩合反应制得(6R,7R)-7-氨基-3-[2-(4-甲基-5-噻唑)乙烯基]-8-氧代-5-硫-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸(7-ATCA,1),其结构经1H NMR,13C NMR和IR表征。考察了离子液体及其用量,原料摩尔比r[n(4-甲基-5-甲酰基噻唑)∶n(2)],反应温度和反应时间对1收率的影响。在最佳反应条件[b为反应介质,b用量为20 m L,r=1.3,于65℃反应5 h]下,1收率可达90%以上。 相似文献
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J Sakaguchi T Higashi T Azuma T Suzuki N Iwasaki N Kondo O Nagata H Kato M Hanaoka 《Chemical & pharmaceutical bulletin》2001,49(6):788-790
A new and facile route for the synthesis of the novel gastrointestinal prokinetic butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (1b), which exhibited potent gastro- and colon-prokinetic activities by oral administration without significant side effects, was established. The key intermediate, butyl 4-amino-1-piperidineacetate (16), was prepared from commercially available 4-amino-1-benzylpiperidine (2) in a high yield with four steps. Compound 1b was prepared by condensation of commercially available 4-amino-5-choloro-2-methoxybenzoic acid (7) with 16 in 84% yield. This improved synthetic route was appropriate for large-scale synthesis of 1b. 相似文献
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A high-performance liquid chromatographic assay for the determination of N-[2(S)-(mercaptomethyl)-3-(2-methylphenyl)-1-oxopropyl]-L-methionine (SCH 42354; II), the active metabolite of the atriopeptidase inhibitor prodrug, N-[2(S)-(acetylthiomethyl)-3-(2-methylphenyl)-1-oxopropyl]-L-methi onine ethyl ester (SCH 42495; I), in human plasma was validated for use in clinical pharmacokinetic studies. Plasma (200 microliters) was processed by protein precipitation with acetone containing the internal standard, N-[2(S)-(mercaptomethyl)-3-(2-methylphenyl)-1-oxopropyl]-L- ethionine (III). Compound II was recovered (ca. 90%) in the supernatant after centrifugation and prepared for injection by the addition of 0.15 M monochloroacetic acid containing 0.2 mM EDTA. Separation of II and III was accomplished on commercially available reversed-phase C8 columns designed for the separation of basic compounds. Both compounds were detected using amperometric detection (+0.125 V versus Ag/AgCl) on a thin-layer Au/Hg amalgam electrode. The lower limit of quantitation was 10 ng/ml, where the inter-assay precision (coefficient of variation) was +/- 11.4% and the inter-assay accuracy (bias) was +1.0%. No endogenous interferences were observed in the extracts obtained from drug-free plasma. The detector response (using either peak area or height ratios of II to III) was linear from 0.01 to 1.0 micrograms/ml. Compound II was stable in plasma supplemented with EDTA and sodium hydrogensulfite for at least 3 months when stored frozen at -78 degrees C; no significant decomposition of II was observed following three freeze-thaw cycles. The feasibility of this liquid chromatographic assay with electrochemical detection was demonstrated with plasma samples from hypertensive subjects administered 100 mg of compound I. 相似文献
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Gialiana Biagi Irene Giorgi Oreste Livi Valerio Scartoni Silvia Velo Pier Luigi Barili 《Journal of heterocyclic chemistry》1996,33(6):1847-1853
A new 4-(benzotriazol-1-yl)-1,2,3-triazole structure was obtained by the diazotization reaction of either of 1-(2-aminophenyl)-4-carboxamido-5-amino-1H-1,2,3-triazole ( 1c ) or of the corresponding Dimroth isomer 1d . It underwent some common reactions to evaluate its chemical behaviour and structure. An analogous reaction sequence was carried out from the 2-nitro-4-methylphenyl azide, to assign the structure to the nitro derivatives prepared. The structure of the new compounds prepared was confirmed by chemical and spectroscopic methods. 相似文献
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Potkin V. I. Petkevich S. K. Kaberdin R. V. Tychinskaya L. Yu. 《Russian Journal of Organic Chemistry》2002,38(9):1271-1276
Reaction of 3,4,4-trichloro-1-(4-methylphenyl)-3-buten-1-one with amines results in replacement of the internal chlorine atom and is accompanied by prototropic allyl rearrangement leading to formation of the corresponding 3-amino-4,4-dichloro-1-(4-methylphenyl)-2-buten-1-ones. The reaction of the title compound with 2,4-dinitrophenylhydrazine yields 3,4,4-trichloro-1-(4-methylphenyl)-3-buten-1-one 2,4-dinitrophenylhydrazone and is not accompanied by allyl rearrangement. 相似文献
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Meryem Fistikci Ozlem Gundogdu Derya Aktas Hasan Secen M. Fethi Sahin Ramazan Altundas Yunus Kara 《Tetrahedron》2012,68(12):2607-2610
A new synthetic strategy for (R)- and (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanoic acid, a building block in the preparation of sitagliptin and its derivatives, was developed. Pd(OAc)2 catalyzed coupling of 2,4,5-trifluoro-1-iodobenzene with allyl alcohol gave 3-(2,4,5-trifluorophenyl)propanal in a yield of 95%. l-Proline catalyzed reaction of the 3-phenylpropanal (in only 1.2 molar equiv) with nitrosobenzene followed by reduction with NaBH4 and Pd/C catalyzed hydrogenation gave (R)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >99% ee and 65% yield. Selective tosylation of primary hydroxyl group of the 1,2-propandiol unit followed by cyanide displacement afforded (R)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile (80%). The nitrile was converted to the title β-hydroxy acid under basic hydrolysis in a yield of 90%. Thus, (R)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanoic acid was prepared enantioselectively from the starting material in four steps and 45% overall yield. The reaction sequence was repeated with d-proline as the catalyst to give (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanoic acid in 45% overall yield and >99% enantiomeric excess. 相似文献
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M. E. Kon’shin A. L. Efremov M. I. Vakhrin A. A. Gorbunov 《Russian Journal of Organic Chemistry》2012,48(4):544-546
Reactions of 2-(phenylamino)benzoic and 2-(phenylamino)- and 2-methyl-6-phenylpyridine-3-carboxylic acid hydrazides with succinic
anhydride in organic solvents at room temperature gave the corresponding 4-(2-aroylhydrazinyl)-4-oxobutanoic acids. The reactions
in boiling acetic acid afforded N-(2,5-dioxopyrrolidin-1-yl)benzamide or N-(2,5-dioxopyrrolidin-1-yl)pyridine-3-carboxamide. 相似文献
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通过反-1-(4-甲基苯基)-2-(4-吡啶基)乙烯(E-MEP)在稀盐酸中的光二聚反应得到了接近定量的标题化合物(DMDPC)。用元素分析,IR, UV, 1H NMR和MS表征了其结构, 并用X射线衍射法测定了DMDPC的晶体结构。DMDPC属单斜晶系, 空间群为P21/c, 晶胞参数a=1.1376(6), b=1.7379(8), c=1.1590(5)nm, β=106.16(4)ⅲ, Z=4。由于四元环同侧苯环和吡啶环的相互排斥作用, DMDPC采取蝶式构象。研究发现, DMDPC在短波紫外光照射下易发生开环反应; 同时还发现,E-MEP与其顺式异构体(Z-MEP)间的反-顺异构化平衡受照射光波长控制。 相似文献
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(S)-2-氨基-1,1-二苯基-1-丙醇是一种合成多种手性助剂的重要中间体,也用于外消旋屈昔多巴前体化合物的拆分。从价廉易得的L-丙氨酸出发,通过四步反应制得,总收率55.6%L-丙氨酸经甲酯化,苄氧羰基保护制得的L-2-苄羰基氨基丙酸甲酯与苯基溴化镁反应制得(S)-2-苄氧羰基氨基-1,1-二苯基-1-丙醇。是在5%Pd/C催化加氢下脱除苄氧羰基得到标题化合物。该制备方法涉及的中间体及目标化合物易于纯化,总收率高且重现性好。我们用制得的氨基醇能成功地拆分外消旋苏式屈昔多巴前体化合物3-3,4-二苄氧苯基)-N-苄氧羰基丙氨酸。 相似文献