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.

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

Methyl 3-（5-bromo-l-ethyl-lH-indole-3-carbonyl）aminopropionate has been synthesized 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/c with a = 11.7927（8）, b = 14.9342（8）, c = 9.0060（5） A, β = 101.558（6）°, V = 1553.93（16） A3, Z = 4, Dc= 1.510 g/cm3, 2 = 0.71073 A,μ（MoKa） = 2.656 mm-1, Mr = 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.

An efficient synthesis of 2,2-bis(1H-indol-3-yl)-2H-acenaphthen-1-one catalyzed by recyclable solid superacid SO_4^(2-)/TiO_2 under grinding condition

An efficient synthesis of symmetrical 2,2-bis（1H-indol-3-yl）-2H-acenaphthen-1-one is achieved via a reaction of acenaphthe-nequinone and indoles catalyzed by solid superacid SO4^2-/TiO2 under solvent-free conditions at room temperature by grinding, which provides an efficient route to the synthesis of symmetrical 2,2-bis（1H-indol-3-yl）-2H-acenaphthen-1-one.This procedure offers several advantages including solvent-free conditions,excellent yields of products,simple work-up as well as reuse of catalysts which makes it a useful and attractive protocol for the synthesis of these compounds.

Adolescent Exposure of JWH-018 “Spice” Produces Subtle Effects on Learning and Memory Performance in Adulthood

The active components associated with the bio-designer drugs known variously as “Spice” or “K2” have rapidly gained in popularity among recreational users, forcing the United States Drug Enforcement Administration to classify these compounds as Schedule I drugs in the Spring of 2011. However, although there is some information about many of the synthetic cannabinoids used in Spice products, little is known about the consequences of the main constituent, (1-pentyl-3-(1-naphthoyl)indole;JWH-018), on neuropsychological development or behavior. In the present experiment, adolescent rats were given repeated injections of either saline or 100 μg/kg of JWH-018. Once the animals were 75 days of age, they were trained using tasks with spatial components of various levels of difficulty and a spatial learning set task. On early trials with water maze tasks of varying difficulty, the JWH-018 treated rats were impaired relative to controls. However, by the end of each phase of testing, drug and control animals were comparable, although on probe trials the drug-treated animals spent significantly less time in the target quadrant. In addition, the performance of the drug-treated rats was inferior to that of the control animals on a learning set task, suggesting some difficulty in adapting their responses to changing task demands. The results suggest that chronic exposure to this potent cannabinoid CB1 receptor agonist during adolescence is capable of producing a variety of subtle changes affecting spatial learning and memory performance in adulthood, well after the drug exposure period.

Fe-catalyzed regioselective Friedel–Crafts hydroxyalkylation of N-substituted glyoxylamide with indoles

An efficient regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with various indoles catalyzed by Lewis acids was developed. The reactions proceeded smoothly at room temperature and the 2-hydroxy-2-（1H-indol-3-yl）-N-substituted acetamide resulted from the reactions catalyzed by FeSO4 were synthesized in excellent yields （up to 93%）. While the bisindole compounds were obtained when FeCl3 was used as a catalyst in excellent yields （up to 92%）. A possible mechanism was proposed.

银催化的3-三氟乙酰基吲哚与异氰酸酯反应:(Z)-β-三氟甲基取代的脱氢色氨酸衍生物的高效合成

实现了银催化的3-三氟乙酰基吲哚与异氰酸酯的环化-重排反应,以优秀的收率(up to>99%)得到了一系列单一构型的(Z)-β-三氟甲基脱氢色氨酸衍生物.反应以克级规模进行时,产率仍能达到98%,这一结果证明了反应的实用性.此外,作者提出了可能的反应机理.该反应具有原子经济性高、反应条件温和及操作简便等优点.

3-三氟乙酰基吲哚的合成研究

以廉价易得的吲哚和三氟乙酸酐为原料,经过傅-克酰基化反应合成得到目标化合物3-三氟乙酰基吲哚,其结构经~1H-NMR和ESI-MS表征。对3-三氟乙酰基吲哚的合成工艺进行研究,确定适宜的反应条件为:物料比为n(三氟乙酸酐)∶n(吲哚)=7∶1,过量的三氟乙酸酐在反应过程中不但是反应物,而且起到溶剂的作用,反应温度为25℃,反应时间4h。在该反应条件下,产物收率为87.5%(以吲哚计)。

Base-controlled annulation of tryptamine-derived isocyanides with nitrile imines for access to polycyclic spiroindoline derivatives

An annulation reaction of tryptamine-derived isocyanides with hydrazonyl chlorides in the presence of bases was developed.Controlled by different bases,[1+2+3]annulation and[1+2+3]/[2+3]annulation cascade were realized.In the latter reaction,five new chemical bonds as well as three new heterocycles were formed in one step.It showed extremely high efficiency,relatively broad substrate scope,milder reaction conditions,good tolerance of functional groups and good chemoselectivity.