Synthesis of N-Substituted Derivatives of 2-(4-Amino-2-methyl-1H-indol-3-yl)- and 2-(6-Amino-2-methyl-1H-indol-3-yl)acetic Acids

A method was developed for the production of indole compounds containing an amino group at positions 4 and 6 of the benzene ring on the basis of the indolization of the 3-acetylaminophenylhydrazone of ethyl levulinate. A series of derivatives of 2-(4-amino-2-methyl-1H-indol-3-yl)- and 2-(6-amino-2-methyl-1H-indol-3-yl)acetic acids at the 4- and 6-amino group were synthesized.     

Formation of the same pyrimido[1,2-a]indoles from 1-(oxiran-2-ylmethyl)-1H-indole or [1,3]oxazolo[3,2-a]indole derivatives in its reactions with aromatic amines

Reactions of two isomers—2-chloro-1-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde or 2-(chloromethyl)-2,3-dihydro[1,3]oxazolo[3,2-a]indole-9-carbaldehyde with aromatic amines lead to the same products in both cases—hydrochlorides of pyrimido[1,2-a]indole derivatives containing two fragments of an amine per one part of the indole nucleus. Its structure was confirmed by X-ray analysis of the crystals base, obtained by alkali treatment of the reaction product (when aryl is 4-MeOC₆H₄).     

Synthesis, Crystal Structure and Fungicidal Activity of 3- ( 4- Chloro- 3- ethyl- 1 -methyl- 1 H- pyrazol- 5-yl ) - 6- (E) phenylvinyltriazolo [ 3, 4-b ] - 1,3, 4-thiadiazole

1　ＩＮＴＲＯＤＵＣＴＩＯＮＩｎｒｅｃｅｎｔｙｅａｒｓ ,ｔｒｉａｚｏｌｏ[3,4, ｂ] 1 ,3,4 ｔｈｉａｄｉａｚｏｌｅｄｅｒｉｖａｔｉｖｅｓｈａｖｅｂｅｅｎａｔ ｔｒａｃｔｉｎｇｍｕｃｈａｔｔｅｎｔｉｏｎｆｒｏｍｃｈｅｍｉｓｔｓａｎｄｐｈａｒｍａｃｏｌｏｇｉｓｔｓｂｅｃａｕｓｅｔｈｅｙｓｈｏｗｂｒｏａｄｓｐｅｃｔｒａｏｆｂｉｏｌｏｇｉｃａｌａｃｔｉｖｉｔｉｅｓ,ｓｕｃｈａｓｉｎｓｅｃｔｉｃｉｄａｌ[1 ] ,ａｎｔｉｆｕｎｇａｌ[2 ] ,ｈｅｒｂｉｃｉｄａｌ[3] ,ａｎ ｔｉｂａｃｔｅｒｉａｌ[4] ,ｈｙｐｏｔｅｎｓｉｖ…     

Synthesis and Crystal Structure of Ethyl 2-(6-(1,3-Dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl) Butanoate

The title compound ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl) butanoate 3 was synthesized by the reaction of ethyl 2-(6-amino-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl) butanoate with 4,5,6,7-tetraydrophthalic anhydride,and its structure was determined by X-ray single-crystal diffraction.The crystal belongs to the monoclinic system,space group P21/n with a = 9.3469(2),b = 16.7715(5),c = 13.7153(4) ,β = 104.9680(10)°,μ = 0.107 mm-1,Mr = 430.42,V = 2077.08(10) 3,Z = 4,Dc = 1.376 g/cm3,F(000) = 904,T = 296(2) K,R = 0.0508 and wR = 0.1478.     

Ultrasound-assisted synthesis of 3-(1-(2-(1H-indol-3-yl)ethyl)-2-aryl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)indolin-2-ones by novel core-shell bio-based nanocatalyst anchoring sulfonated L-histidine on magnetized silica (SO3H-L-His@SiO2-nano Fe3O4)

An efficient synthesis of 3-(1-(2-(1H-indol-3-yl)ethyl)-2-aryl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)indolin-2-ones is reported via a one-pot three-component reaction of 3-phenacylidenoxindoles, tryptamine, and dimedone under ultrasound irradiation using a newly prepared core-shell nanostructure. The utilized nanocatalyst is obtained by anchoring sulfonated L-histidine amino acid shell, as the bio part, on silica-nanomagnetite core (SO₃H-L-His@SiO₂-nano Fe₃O₄) and characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy (¹H NMR), field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric/differential thermal analysis, vibrating sample magnetometer measurements, transmission electron microscopy, and back-titration. The protocol contains several advantages, such as relatively short reaction times, simple work-up procedure by separation of the catalyst with an external magnet, the use of economical and environmentally friendly ultrasonic waves, and reusability and recoverability of the core-shell nano-promoter for three runs without significant activity loss.     

“一锅串联法”合成2-[(E)-2-2-氯-1-甲基-3-吲哚基)乙烯基]喹啉-3-羧酸(英文)

设计了以2-(溴甲基)喹啉-3-甲酸乙酯(4)与2-氯-1-甲基-3-吲哚醛(5)为起始化合物,通过简便有效的"一锅法"反应,首次将吲哚环引入2-苯乙烯基喹啉骨架模型,从而得到一新颖结构的双杂环化合物,即(E)-2-(2-(2-氯-1-甲基-1H-3-吲哚基)乙烯基)喹啉-3-羧酸(3),其结构通过波谱数据和元素分析得以证实。     

Rapid and Efficient Synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-ones Catalyzed by p-TSA

An efficient synthesis of 3,3-di(1H-indol-3-yl)indolin-2-ones and 2,2-di(1H-indol-3-yl)-2H-acenaphthen-1-ones via a reaction of various isatins or acenaphthenequinone with indoles in the presence of p-methylbenzene sulfonic acid (p-TSA) in CH₂Cl₂ at room temperature is described. The advantages of this method include good reaction yield, simple workup procedure, and mild reaction condition.     

Synthesis and Antibacterial Activities of 4-Amino-3-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-5-mercapto-1,2,4-triazoles/2-Amino-5-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-1,3,4-thiadiazoles and Their Derivatives

ＩｎｔｒｏｄｕｃｔｉｏｎＳｃｈｉｆｆｂａｓｅｓ ,ａｍｉｄｅｓ ,ｉｍｉｄａｚｏｌｏ[2 ,1 ｂ] 1,3,4 ｔｈｉａｄｉａｚｏｌｅｓ,ａｎｄ 7Ｈ ｓ ｔｒｉａｚｏｌｏ[3,4 ｂ] 1,3,4 ｔｈｉａｄｉ ａｚｉｎｅｓｃｏｎｔａｉｎｉｎｇｈｅｔｅｒｏｃｙｃｌｅｓｈａｖｅｂｅｅｎａｔｔｒａｃｔｉｎｇｍｕｃｈａｔｔｅｎｔｉｏｎａｓｐｏｔｅｎｔｉａｌａｎｔｉｆｕｎｇａｌａｇｅｎｔｓ .1 51,2 ,3 ｔｒｉａ ｚｏｌｅ ,6 7ｍｅｒｃａｐｔｏ 1,2 ,4 ｔｒｉａｚｏｌｅ ,81,3,4 ｔｈｉａｄｉａｚｏｌｅ9 10ａｎｄｔｈｅｉｒｒｅｌａｔｅｄｃｏ…     

Synthesis and Crystal Structure of Methyl(7,7-Dimethyl-2-amino-4-(4-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran-3-yl)Carboxylate

<正>The title compound methyl (7,7-dimemyl-2-amino-4-(4-chlorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran-3-yl) carboxylate (C19H20ClNO4, Mr = 361.81) was synthesized and crystallized. The crystal belongs to triclinic, space group P 1 with a = 8.519(2), b = 10.346(2), c = 11.481(3) A, α = 108.16(1), β = 107.78(2), γ= 91.83(2)°, Z = 2, V = 906.5(3) A3, Dc = 1.326 g/cm3, μ(MoKα) = 0.234 mm-1, F(000) = 380, R = 0.0467 and wR = 0.1270 for 3142 observed reflections (I > 2σ(I)). X-ray analysis reveals that the C(7), C(8), C(9), O(1), C(10) and C(11) atoms form a six-membered ring which adopts a boat conformation. In the ring, the distances of C(8)-C(9) and C(10)-C(11) are 1.332(3) and 1.357(3) A, respectively, which indicates that they are C=C double bonds. Another six-membered ring (C(8)-C(9)-C(15)-C(14)-C(13)-C(12)) adopts the half-chair confonnation. In addition, there are intermolecular hydrogen bonds in the crystal structure.     

Synthesis and Crystal Structure of 7,7- Dimethyl-2-amino-3-cyano-4-(3,4-methylenedioxylphenyl)- 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran

1 INTRODUCTION Inorganic solid supports as catalysts resulting in higher selectivity, milder conditions and easier work-up has been reported as useful catalysts for many reactions [1~3]. Recently, we have reported the Knoevenagel condensation and some other reactions[4~6] catalyzed by KF-Al2O3. In this paper, we discussed the crystal structure of the title compound synthesized by the reaction of 2-cyano-3-(3,4-methylenedioxylphenyl)acrylonitrile and 5,5-dimethyl-1,3-cyclohexanedione in…     

1-(2-苯并呋喃酰基)愈创兰烃薁的合成

在路易斯酸作用下, 以氯乙酰氯为酰基化试剂, 对愈创兰烃薁进行了酰化反应研究, 将氯乙酰化产物与水杨醛在温和反应条件下进行缩合, 以较好的收率、高选择性地得到1-(2-苯并[b]呋喃酰基)兰烃薁类衍生物, 其结构经1H NMR, IR及元素分析等得以证实.     

新型含1,2,4-三唑基的1,5-苯并硫氮杂的合成和表征

以α-溴代苯乙酮为原料,在三乙胺作用下制备α-(1,2,4-三唑-1-基)-芳基乙酮(1a～1c),再与芳香醛发生羟醛缩合反应制备相应的含三唑基的查尔酮2a～2l,将中间体2a～2l同邻氨基硫酚合成新型的2,4-二芳基-3-(1,2,4-三唑-1-基)-2,3-二氢-1,5-苯并硫氮杂(3a～3l).所得化合物的结构经元素分析,IR,MS和1HNMR确认,同时用X射线衍射法测定了化合物2a和3a的晶体结构.     

An unexpected acid mediated rearrangement of monoethylene ketal of 2-methyl-2-(3-methylbut-2-en-1-yl)cyclohex-4-ene-1,3-diones to chromane

We herein report a serendipitously observed acid mediated rearrangement of monoethylene ketal of 2-methyl-2-(3-methylbut-2-en-1-yl)cyclohex-4-ene-1,3-diones to Dihydrobenzopyran and demonstrated the application of this methodology in the construction of core carbon scaffolds of dimethoxyajacareubin, cariphenone-A and crotamadine.     

Synthesis of 5-Hydroxymethyl-8-methyl-3-(3-aryl-[1,2,4]oxadiazol-5-yl)-2H-pyrano[2,3-c]pyridin-2-ones and Their Esters

New 5-hydroxymethyl-8-methyl-3-(3-aryl-[1,2,4]oxadiazol-5-yl)-2H-pyrano-[2,3-c]pyridin-2-ones and their esters were synthesized. The structure of obtained compounds was determined through a complete ¹H NMR analysis.     

Convenient,DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP

During attempts to involve 5-methyl-2-phenyl-1-(3-phenyl-prop-2-yn-1-yl)-1H-imidazole in a base-promoted, allene-mediated cyclization of the alkyne moiety onto the nearby aromatic ring, substantial amount of the ketone resulting from hydration of the alkyne with adventitious water was discovered. The formation of the ketone of the anti-Markovnikov alkyne hydration was developed into a preparative method. This method, alternative to the common acid-and metal-catalyzed approaches, may be of particular utility when alkyne hydration needs to be performed in the presence of acid-labile groups.     

Crystal Structure of Ethyl 4-benzoyl-1a,2,3,4-tetrahydro-3-methyl-1a-(4-methylphenyl)-1H-azirino〔1,2-a〕〔1,5〕 benzodiazepine-1-carboxylate(C_(28)H_(28)N_2O_3)

１ＩＮＴＲＯＤＵＣＴＩＯＮＢｅｎｚｏｄｉａｚｅｐｉｎｅｃｏｍｐｏｕｎｄｓａｒｅｉｍｐｏｒｔａｎｔｐｈａｒｍａｃｅｕｔｉｃａｌａｇｅｎｔｓ〔１,２〕．Ｒｅｃｅｎｔｌｙｉｔｈａｓｂｅｅｎｆｏｕｎｄｔｈａｔｂｅｎｚｏｄｉａｚｅｐｉｎｅｔｒｉｃｙｃｌｉｃｄｅ...     

Synthesis and in vitro Antimicrobial Activity of New Ethyl 2-(Ethoxyphosphono)-1-cyano-2-(substituted tetrazolo-[1,5-a]quinolin-4-yl)ethanoate Derivatives

A series of new ethyl 2‐(ethoxyphosphono)‐1‐cyano‐2‐(substituted tetrazolo[1,5‐a]quinolin‐4‐yl)ethanoate derivatives have been synthesized for the first time of tetrazolo[1,5‐a]quinoline derivatives. Elemental analysis, IR, ¹H NMR, ¹³C NMR, ³¹P NMR and mass spectral data elucidated the structures of the all newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds have been investigated against Gram‐positive Bacillus subtilis, Gram‐negative Escherichia coli and two fungi Candida albicans and Aspergillus niger in comparison with standard drugs. Significantly microbiological behavior of these newly synthesized derivatives possesses significant antibacterial and antifungal activity.     

Synthesis and Crystal Structure of 7-Amino-2,3,4,5-tetrahydro- 1,3-dimethyl- 5-（2-nitrophenyl）-2,4-dioxo-lH-pyrano[2,3- d]pyrimidine-6-carbonitrile DMF Solvate

The title compound 7-amino-2,3,4,5-tetrahydro-1,3-dimethyl-5-（2-nitrophenyl）- 2,4- dioxo-1H-pyrano[2,3-d] pyrirnidine-6-carbonitrile DMF solvate 1 （C19H20N6O6, Mr = 428.41） was synthesized and crystallized. The crystal belongs to the monoclinic system, space group P2 1/c with a = 11.383（2）, b = 13.372（2）, c = 13.673（2）A, β = 97.380（4）°, Z = 4, V = 2063.8（6）A^3, Dc = 1.379 g/cm^3,μ（MoKα） = 0.105 mm^-1, F（000） = 896, the final R = 0.0738 and wR = 0.1647 for 2964 observed reflections （I〉 2σ（I））. X-ray analysis reveals that the new pyran ring is coplanar, which is obviously different from those of other similar compounds. In addition, the unclassical hydrogen bonds of C-H…O and C-H…N are presented in the crystals except for the normal hydrogen bonds of N-H…O.