Synthesis and Crystal Structure of 3-（1-Ethyl-1H-indole-3-carbonyl）aminopropionic Acid

3-(1-Ethyl-1H-indole-3-carbonyl)aminopropionic acid has been synthesized by alkylation of 3-(1H-indole-3-carbonyl)aminopropionic acid methyl ester with bromoethane,follo-wed by saponifying and acidating,in 89.0% yield.Its crystal structure was gotten and determined by X-ray diffraction method.The crystal is of orthorhombic,space group P212121 with a = 8.9490(12),b = 11.1010(15),c = 13.0475(18) ,V = 1296.2(3) 3,Z = 4,Dc = 1.334 g/cm3,λ = 0.71073 ,μ(MoKα) = 0.095 mm-1,Mr = 260.29 and F(000) = 552.The structure was refined to R = 0.0306 and wR = 0.1445 for 2612 observed reflections with I 2σ(I).In the crystal structure,molecules are linked to each other through hydrogen bonds of N(2)-H(2)···O(1) and O(3)-H(3)···O(1),generating a three-dimensional network.     

(2S,4S)-苯甲基-2-(6-氟-1H-吲哚-3-羰基)-4-羟基-吡咯烷-1-羧酸酯的合成

以4-羟基-L-脯氨酸为原料,经Cbz保护、偶联、Mitsunobu反应和水解合成了抗肿瘤新药Birinapant的重要中间体--(2S,4S)-苯甲基-2-(6-氟-1H-吲哚-3-羰基)-4-羟基吡咯烷-1-羧酸酯,总收率83%,其结构经¹H NMR和ESI-MS确证。     

Synthesis and Antivirus Activities of Novel Triazoly1-3 (2H) -2H-chromen-2-ones

设计并合成了6个未见文献报道的三唑席夫碱苯并吡喃酮类化合物,其结构经1H NMR,IR和元素分析表征.初步生物活性测试结果表明,用量为500 mg·L-1时,部分化合物对黄瓜花叶病毒有一定的抑制作用.     

Synthesis and Crystal Structure of Methyl 3-（5- Bromo-1-ethyl-1H-indole-3-carbonyl）aminopropionate

Methyl 3-(5-bromo-1-ethyl-1H-indole-3-carbonyl)aminopropionate has been syn-thesized by the acylation of 5-bromo-3-trichloroacetylindole with β-alanine methyl ester,followed by alkylation with ethyl iodide,in 82.6% yield.Its crystal structure was gotten and determined by X-ray diffraction method.The crystal is of monoclinic,space group P2 1 /c with a=11.7927(8),b=14.9342(8),c=9.0060(5),β=101.558(6)°,V=1553.93(16)3,Z=4,D c=1.510 g/cm 3,λ=0.71073,μ(MoKα)=2.656 mm-1,M r=353.22 and F(000)=720.The structure was refined to R=0.0401 and wR=0.0825 for 1704 observed reflections with I > 2σ(I).In the crystal structure,intermolecular N(2)-H(2)···O(1) hydrogen bond and weak intermolecular bonds (C(1)-H(1) O(1) and C(10)-H(10B) O(2)) are formed,and π-π stacking also exists.     

Synthesis of 5-Aryl(heteryl)-1-hydroxyethyl-4-(furyl-2-carbonyl)-3-hydroxy-3-pyrroline-2-ones

5-Aryl(heteryl)-1-hydroxyethyl-4-(furyl-2-carbonyl)-3-hydroxy-3-pyrroline-2-ones were synthesized via reactions of methyl ester of furyl-2-carbonylpyruvic acid with a mixture of aromatic or heterocyclic aldehyde and ethanolamine in dioxane. Antibacterial and antifungal activities of the synthesized compounds was studied.     

Synthesis of 3-(quinoxalin-2-yl)-2H-chromen-2-ones under microwave irradiation

Abstract  A facile procedure for the synthesis of quinoxalines is being reported starting from 3-(2-bromoacetyl)coumarins or 3-(2-bromobutanoyl)coumarins and substituted o-phenylenediamines. The reactions were carried out under catalyst-free and microwave irradiation conditions producing the title compounds in moderate to excellent yields in a short time with easy workup. The structures of all new compounds have been confirmed on the basis of their IR, ¹H NMR, ¹³C NMR, and HRMS data. Graphical Abstract        

Synthesis of 3-alkylamino-3-(2-hydroxyaryl)-1-polyfluoroalkylprop-2-en-1-ones and 2-polyfluoroalkyl-4H-chromen-4-imines

Condensation of Schiff"s bases (prepared from 2-hydroxy- or 2-hydroxy-5-methylacetophenones and primary amines) with ethyl polyfluoroalkanoates in the presence of LiH in THF affords 3-alkylamino-3-(2-hydroxyaryl)-1-polyfluoroalkylprop-2-en-1-ones, which undergo cyclization in acidic media into 2-polyfluoroalkyl-4H-chromen-4-iminium salts. When neutralized with aqueous ammonia, the latter give 2-polyfluoroalkyl-4H-chromen-4-imines in high yields.     

三唑席夫碱苯并吡喃酮衍生物的合成及其抗病毒活性

设计并合成了6个未见文献报道的三唑席夫碱苯并吡喃酮类化合物,其结构经1H NMR,IR和元素分析表征。初步生物活性测试结果表明,用量为500 mg·L-1时,部分化合物对黄瓜花叶病毒有一定的抑制作用。     

Efficient,Stereoselective Approach to the Synthesis of 3-(1-Phenyl-2-(Z-styrylsulfonyl)-1H-imidazol-4-yl)-2H-chromen-2-ones

Reaction of phenyl acetylene with 3-(1-aryl-2-mercapto-4-imidazolyl)-2H-1-benzopyran-2-ones (4) in the presence of sodium hydroxide in absolute ethanol led to the formation of 3-(1-phenyl-2-(Z-styrylthio)-1H-imidazol-4-yl)-2H-chromen-2-ones (6) in excellent yields. These, on further oxidation with H₂O₂/AcOH, gave the corresponding sulfones (7) with retention of stereochemistry.

Synthesis and Antimicrobial Activity of 5-(Het)aryl-3-hydroxy-1-hydroxyethyl-4-(thienyl-2-carbonyl)-3-pyrrolin-2-ones

Russian Journal of General Chemistry - A series of novel 5-(het)aryl-3-hydroxy-1-hydroxyethyl-4-(thienyl-2-carbonyl)-3-pyrrolin-2-ones was synthesized by reacting methyl thienyl-2-carbonylpyruvate...     

Reaction of 3-(3-Arylpropenoyl)-2H-chromen-2-ones with Methyl 1-Bromocyclopentane-1-carboxylate and Zinc

Russian Journal of Organic Chemistry - The reaction of 3-(3-arylpropenoyl)-2H-chromen-2-ones with methyl 1-bromocyclopentane-1-carboxylate and zinc resulted in the isolation, after hydrolysis of...     

N-(3-吲哚甲酰基)-β-丙氨酸甲酯的结构鉴定

为研究吲哚衍生物的生理活性,对吲哚进行三氯乙酰化、并与β-丙氨酸甲酯缩合,合成了含吲哚环氨基酸甲酯.通过1H NMR,IR,MS和元素分析对产物结构进行了鉴定,确证其为N-(3-吲哚甲酰基)-β-丙氨酸甲酯.     

Synthesis, stereochemistry, and antimicrobial activity of 2,6-diaryl-3-(arylthio)piperidin-4-ones

A series of novel 2,6-diaryl-3-(arylthio)piperidin-4-ones have been synthesized by reaction of arylthioacetones, substituted aromatic aldehydes, and methylamine/ammonium acetate and their structures elucidated by (1)H, (13)C, and 2D NMR (H, H-COSY, C, H-COSY, HMBC, and NOESY) spectroscopy. The NMR data reveal that all these piperidones exist in chair conformation with the 2,6-diaryl groups equatorially oriented, while the arylthio group prefers to be in either an equatorial or axial orientation depending on whether the substituent in the 2,6-diaryl rings is present in 4- or 2-position, respectively. In the case of NH-2,6-diaryl-3-(arylthio)piperidin-4-ones with o-substituted 2,6-diaryl groups, the arylthio group prefers the axial orientation presumably in a bid to minimize the steric and/or electronic repulsion. The arylthiopiperidin-4-ones exhibit significant antibacterial activity against Staphylococcus aureus, Vibrio cholerae, Salmonella typhi, and Escherichia coli and antifungal activity against Candida albicans and Aspergillus niger.     

Synthesis of 1-(2-furyl)-2-nitropropen-3-ones

1-(2-Furyl)-2-nitropropen-3-ones were synthesized by reaction of nitrogen tetroxide with a number of , -unsaturated furylcarbonyl compounds. The 5-nitrofuryl derivative was obtained from 1-(2-furyl)-3-(4-methoxyphenyl)propen-3-one when the excess amount of N₂O₄ was increased. Replacement of bromine by a nitro group in the furan ring is observed in the case of the 5-bromofuryl derivative.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1604–1606, December, 1977.     

Synthesis of Esters of 3-(2-Aminoethyl)-1H-indole-2-acetic Acid and 3-(2-aminoethyl)-1H-indole-2-malonic acid (= 2-[3-(2-aminoethyl)-1H-indol-2-yl]propanedioic acid) 4th communication on indoles,indolenines, and indolines

Alkyl 3-(2-aminoethyl)-1H-indole-2-acetates 6a and 6b are synthesized starting from methyl 1H-indole-2-acetate (2) via methyl 3-(2-nitroethenyl)-1H-indole-2-acetate (4) and the alkyl 3-(2-nitroethyl)-1H-indole-2-acetates 5a and (Scheme 1). Analogously, diisopropyl 3-(2-aminoethyl)-1H-indole-2-malonate 20b is obtained from diisopropyl 1H-indole-2-malonate 11c (Scheme 4). An alternative synthesis of 20a and 20b follows a route via 15–18 and the dialkyl 3-(2-azidoethyl)-1H-indole-2-malonates 19a and 19b , respectively (Scheme 3). The aminoethyl compounds 6a and 20a are easily transformed into lactams 7 and 21 , respectively. Procedures for the preparation of the indoles 2 and 11a and of the alkylating agent 14 are described. A tautomer 12 of 11a is isolated.     

Synthesis of 2-substituted 3-iodo-4H-chromen-4-ones

3-Iodochromones containing phenyl and furyl fragments at position 2 were synthesized by heterocyclization of β-ketoenamines.     

Synthesis,characterization, NLO study,and antimicrobial activities of metal complexes derived from 3-(3-(2-hydroxyphenyl)-3-oxoprop-1-enyl)-4H-chromen-4-one and sulfanilamide

A series of metal(II) complexes ML (where M?=?Cu(II), Co(II), Ni(II), Zn(II), Mn(II), Cd(II), and VO(II)) have been prepared from 3-(3-(2-hydroxyphenyl)-3-oxoprop-1-enyl)-4H-chromen-4-one and sulfanilamide. The structures of the complexes have been investigated by elemental analysis, magnetic susceptibility, molar conductance, IR, UV-Vis, NMR, mass, and ESR spectral studies. Conductivity measurements reveal that the complexes are non-electrolytes, except the oxovanadium complex. Spectral and other data show square pyramidal geometry for oxovanadium and octahedral for the other complexes. The redox behaviors of the copper and vanadyl complexes have been studied through cyclic voltammetry. Antimicrobial activities of the compounds against several microorganisms indicate that some complexes have higher activity than free ligand. The compounds may serve as photoactive materials as indicated from their characteristic fluorescence properties. The second harmonic generation efficiency of the ligand was found to be higher than that of urea and KDP.     

Photocyclisation of 3-alkoxy-6-chloro-2-(3-methylthiophen-2-yl)-4H-chromen-4-ones

Photocyclisation of 3-alkoxy-6-chloro-2-(3-methylthiophen-2-yl)-4H-chromen-4-ones in methanol with pyrex filtered UV-light lead to the formation of tetracyclic compounds through intramolecular γ-hydrogen abstraction. The methyl group on the thiophenyl ring does not interfere in the photocyclisation although it does effect the product formation.