Direct Conversion of 3-(2-Nitroethyl)-1H-Indoles into 2-(1H-Indol-2-yl)Acetonitriles

The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules.     

Improved Method for Preparation of 3-(1H-Indol-3-yl)benzofuran-2(3H)-ones

3-(1H-Indol-3-yl)benzofuran-2(3H)-ones were efficiently accessed via polyphosphoric acid-mediated condensation of 3-(2-nitrovinyl)-1H-indoles with phenols.     

Chemistry of 3-(2-Haloacyl)indoles

This review presents a systematic and comprehensive survey of the methods ofpreparation and the chemical reactivity of 3-(2-haloacyl)indoles. These compounds are important intermediates for the synthesis of a variety of otherwise difficult to obtain synthetically useful and novel heterocyclic systems. The data published over the past few years are reviewed here for the first time.     

5-(1H-Indol-3-yl)-pyrazolyl derivatives as colorimetric sensor for anions

The synthesis, characterisation and binding and deprotonation studies with anions for four 5-(1H-indol-3-yl)-pyrazolyl derivatives (2–5) have been described. It is worthy to mention that sensor 2 shows a drastic change in absorption spectrum (ca. 335 nm) and colour (colourless to blue) upon addition of F^? in DMSO solution due to the deprotonation of indole –NH proton, as confirmed by ¹H NMR titration. Sensor 4 recognizes F^? and CN^? ions by deprotonation mechanism with visible colour change of the solution in a similar manner to that of 2. However, in contrary to 2 and 4, sensor 3 binds with F^?, CN^?, H₂PO₄ ^?, AcO^? and PhCOO^? ions exploiting hydrogen-bonding interaction with the shifting of absorption band to longer wavelength and subsequent colour change of the solution. Compound 5 recognizes F^? without any visual colour change and its binding is studied by ¹H NMR titration to acquire the important information about the nature of binding between F^? and 5.     

Chemistry of 3-Oxo-N-(pyridin-2-yl)butanamide and Related Compounds

This review highlights the methods used for the synthesis of 3-oxo-N-(pyridin-2-yl)butanamide compounds. The reactivity and synthetic importance are investigated. In this context, recent progress in the synthesis and use of 3-oxo-N-(pyridin-2-yl)butanamide as precursors for heterocyclic compounds is reviewed. The synthetic routes for preparation of 3-oxo-N-(pyridin-2-yl)butanamide are based on the reaction of diketene with aromatic primary amine and reaction of 2-aminopyridine with β-keto-t-butylthioester or ethylacetoacetate. The bibliography includes 73 references.     

2-(2,4-二氟苯基)-1-(4-烃基派嗪-1-基)-3-(1,2,4-三唑-1-基)-2-丙醇类化合物的合成及抗真菌活性

近20年来,真菌感染特别是深部真菌感染日益引起人们的广泛关注[1]。三唑类抗真菌药物对真菌的选择性较高,代谢稳定,体内动态、安全性都较好,已成为目前抗真菌药物研究开发的重点[2]。三唑类抗真菌药物是细胞色素P450 14α 去甲基酶的抑制剂,可影响该酶所催化的真菌麦角甾醇的生物合成,导致真菌细胞膜破损而死亡[3,4]。1998年,SynPhar实验室及Taiho制药公司[5]研制开发的化合物Syn 2869采用了取代哌嗪作为侧链。体外实验表明,该化合物抗菌谱广,对多种念珠菌、隐球菌及曲莓菌均有效,体内实验中,与目前临床上治疗真菌感染的主要用药伊曲…     

L-Proline-Catalyzed Knoevenagel Condensation: A Facile,Green Synthesis of (E)-Ethyl 2-Cyano-3-(1H-indol-3-yl)acrylates and (E)-3-(1H-Indol-3-yl)acrylonitriles

L-Proline has been utilized as a novel and ecofriendly catalyst in ethanol medium for the Knoevenagel condensation of indole-3-carboxyaldehydes and their N-methyl derivatives 1(a–e) and 4(a–e) with the active methylene compound, ethyl cyanoacetate (2) to afford substituted (E)-ethyl 2-cyano-3-(1H-indol-3-yl)acrylates 3(a–e) and 5(a–e) respectively. These products were reacted with dimethyl sulfate in the presence of PEG-600 as an efficient and green solvent to afford the corresponding N-mthylated derivatives 5(a–e). These Knoevenagel products react with 5% NaOH, yielding (E)-3-(1H-indol-3-yl)acrylonitriles 6(a–e) and 7(a–e).     

Four-Component Domino Reaction for the Synthesis of 1-(1H-Indol-2-yl)-1H-pyrazolo[1,2-b]phthalazine-5,10-diones

Facile, efficient, four-component domino reaction of dialkylphthalates, hydrazine hydrate, indole-3-carboxaldehydes, and malononitrile/ethyl cyanoacetate leads to the formation of 1-(1H-indol-2-yl)-1H-pyrazolo [1,2-b] phthalazine-5,10-diones in the presence of InCl₃ as catalyst in refluxing ethanol for 1 h in good yields. This four-component domino reaction transformation presumably proceeds via sequential addition, dehydration, condensation, and cyclization steps.     

Synthesis,Crystal Structure,Antitumor Activities and Docking Study of 1-(2-(1H-Indol-3-yl)ethyl)-3-(2-methoxyphenyl)urea

The title compound,1-(2-(1 H-indol-3-yl)ethyl)-3-(2-methoxyphenyl)urea(C_(18)H_(19)N_3O_2,M_r = 309.36) has been synthesized,and its structure was characterized by ~1H-NMR,~(13)C-NMR,ESI-MS and single-crystal X-ray diffraction.It crystallizes in the monoclinic space group P2_1/c with a = 16.2774(15),b = 11.1082(10),c = 9.0819(3) ?,β = 103.09(9)°,V = 1599.5(3) ?~3,Z = 4,T = 293(2) K,μ(MoKα) = 0.086 mm~(-1),D_c = 1.285 g/cm~3,F(000) = 656 and GOOF = 0.981.5973 reflections were measured(7.04≤2θ≤52.04°),and 3143 were unique(Rint= 0.0393,Rsigma = 0.0546) and used in all calculations.The final R = 0.0756(I 2σ(I)) and w R = 0.1976(all data).The antitumor activity of the title compound was analyzed by MTT assay.Meanwhile,to rationalize its potencies in the CDK4 target,the title compound was docked into CDK4 protein and the interactions with the active site residues were analyzed.     

Synthesis of 1-[2-(1H-Indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-ones

Russian Journal of General Chemistry - 1-[2-(1H-indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrole-2(5H)-ones were synthesized by the short heating of a mixture of tryptamine, aromatic...     

N-甲基-2-(4-取代哌嗪)-N-[3-(萘氧基)-3-(2-噻吩基)丙基]乙酰胺衍生物的设计与合成

以N-甲基-3-(1-萘氧基)-3-(2-噻吩基)-丙胺(度洛西汀)为原料,通过N-酰氯化反应和N-烷基化反应,合成了5个新型的N-甲基-2-(4-取代哌嗪)-N-[3-(萘氧基)-3-(2-噻吩基)丙基]酰胺衍生物,其结构经1H NMR,IR和MS表征。     

2-溴-3-(1H-吲哚-3)-N-甲基马来酰亚胺的合成

以琥珀酰亚胺为起始原料,经过溴化、甲基化后再与吲哚溴化镁加成反应合成了2-溴-3-(1H-吲哚-3)-N-甲基马来酰亚胺,总收率44.8%,其结构经1H NMR和IR确证.     

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)酰胺类新化合物的合成及生物活性

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.     

3-芳基-1-(吡啶-3-基)-2-(1H-1,2,4-三唑-1-基)-2-丙烯-1-醇的合成及生物活性研究

用硼氢化钠还原3-芳基-1-(吡啶-3-基)-2-(1H-1,2,4-三唑-1-基)丙烯酮, 合成了10个新型含吡啶基的三唑醇类化合物. 所有化合物均经核磁、元素分析确证. 生物活性测试结果表明, 部分化合物具有一定的杀菌活性及植物生长调节活性.     

N-[2-(1H-吲哚-3)乙基]-2-乙酰噻唑-4-甲酰胺及其类似物的合成

N-[2-(1H-吲哚-3)乙基]-2-乙酰噻唑-4-甲酰胺是最近从海洋细菌中分离得到的一种新型的天然杀藻剂, 以D-丙氨酸为原料合成了该化合物, 并用类似的方法首次合成了它的类似物2, 3和4. 其关键步骤为通过将取代的4-噻唑甲酸制成混酐与色胺连接的偶联反应. 各中间体都通过¹H NMR和¹³C NMR得到证实. 最终产品通过¹H NMR, ¹³C NMR和HRMS证实, 与文献所报道相一致.     

Synthesis and Crystal Structure of （S）-Ethyl-2-（2-methoxy-phenylsulfenamido）-3-（1H-indol-3-yl）propanoate

With an aim to discover novel AHAS inhibitors,the title compound (S)-ethyl-2(2-methoxy-phenylsulfenamido)-3-(1H-indol-3-yl)propanoate (C 21 H 22 N 2 O 4 S,M r=398.47) has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis.The crystal belongs to orthorhombic,space group P2 1 2 1 2 1 with a=8.078(2),b=12.824(4),c=18.788(6),V=1946.2(10) 3,Z=4,F(000)=840,D c=1.360 mg/m 3,μ=0.197 mm-1,the final R=0.0433 and wR=0.1035 for 3075 observed reflections with I > 2σ(Ⅰ).The absolute structure Flack parameter X of this compound is 0.00(8).A total of 14375 reflections were collected,of which 3431 were independent (R int=0.0437).X-ray analysis reveals that the crystal structure involves two intermolecular N-H···O and one N-H···S intermolecular hydrogen bonds with the neighboring molecules.The crystal structure was compared with our previously reported (S)-methyl 2-(4-R-phenylsulfonamido)-3-(1H-indol-3-yl)propanoate (R=H(1) and Cl(2)),which provided some useful information of these compounds.     

1-(3-吡唑基)薁-3-甲酸甲酯类衍生物的合成

室温下,1-乙酰基薁-3-甲酸甲酯与N,N-二甲酰胺缩甲醛缩合后再与肼或苯肼反应,合成了6个新的1-(3-吡唑基)薁类衍生物,其结构经1HNMR,MS和元素分析表征。并对反应机理进行了探讨。     

1-(嘧啶基-4)-3-(2,6-二氟苯甲酰基)脲衍生物的合成与生物活性

为了寻找高效、低毒、低残留的环境友好杀虫剂, 设计并合成了12个新的1-(嘧啶基-4)-3-(2,6-二氟苯甲酰基)脲衍生物6a～6l, 其结构经IR, ¹H NMR, LC/MS和元素分析确证. 初步生物活性测试结果表明, 部分化合物具有明显的杀虫活性, 如6g在100 mg/L浓度下, 对粘虫(Mythimna sepatara)具有100%的杀虫活性.     

Synthesis and Crystal Structure of N-(2-(1-butyl-3-phenylureido)-1H-indol-3-yl)-N-(4-chlorophenyl)benzamide

<正>The title compound N-(2-(1-butyl-3-phenylureido)-1H-indol-3-yl)-N-(4-chloro- phenyl)- benzamide (C_(32)H_(29)ClN_4O_2, M_r = 537.04) was synthesized by a sequential Ugi four com- ponent condensation (4CC)/aza-Wittig/carbodiimide-mediated cyclization, and the structure was characterized by NMR, IR, MS, elemental analysis and X-ray single-crystal diffraction analysis. The crystal belongs to orthorhombic, space group P2_12_12_1 with a = 11.3663(9), b = 13.3248(10), c = 18.7887(15), V = 2845.6(4)~3, Z = 4, D_c = 1.254 mg/m3, μ = 0.170 mm~(-1), F(000) = 1128, the final R = 0.0538 and wR = 0.1187. X-ray analysis reveals that the new five-membered ring (C(14)-C(15)-N(2)-C(16)-C(21)) and the benzene ring (C(16)-C(21)) are nearly coplanar.