cas 3189-13-7, 6-Methoxyindole | Articles data

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Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis
A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.
Ogura, Akihiro,Shibata, Kouhei,Takao, Ken-Ichi
p. 10067 - 10087
(2021/07/26)

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.
Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
supporting information
p. 7738 - 7744
(2021/05/07)

Preparation method of indole compound
The invention discloses a preparation method of a novel efficient indole compound, which comprises the following steps: by using o-nitroalkylbenzene containing various substituents as a raw material,controlling the reaction temperature to be 70-160 DEG C in an organic solution under the protection of inert gas and the participation of inorganic base, thereby obtaining the indole compound; preparing the novel indole compound containing various substituent groups through a hydrocarbon activation reaction catalyzed by a metal rhodium catalyst. The synthetic method is not reported in literature,the raw materials are easy to synthesize, no reducing agent needs to be added additionally, the method is simple in step, the indole compound containing various substituent groups does not need to beconstructed in one step through a nitroso intermediate, and the yield is high; The method is simple in unit operation, low in equipment requirement and suitable for rapidly synthesizing the indole compounds containing various substituent groups.
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Paragraph 0038-0039

(2020/12/29)

Monoamine Oxidase (MAO-N) Biocatalyzed Synthesis of Indoles from Indolines Prepared via Photocatalytic Cyclization/Arylative Dearomatization
The biocatalytic aromatization of indolines into indole derivatives exploiting monoamine oxidase (MAO-N) enzymes is presented. Indoline substrates were prepared via photocatalytic cyclization of arylaniline precursors or via arylative dearomatization of unsubstituted indoles and in turn chemoselectively aromatized by the MAO-N D11 whole cell biocatalyst. Computational docking studies of the indoline substrates in the MAO-N D11 catalytic site allowed for the rationalization of the biocatalytic mechanism and experimental results of the biotransformation. This methodology represents an efficient example of biocatalytic synthesis of indole derivatives and offers a facile approach to access these aromatic heterocycles under mild reaction conditions.
Black, Gary W.,Brancale, Andrea,Castagnolo, Daniele,Colonna, Serena,Ferla, Salvatore,Masci, Domiziana,Turner, Nicholas J.,Varricchio, Carmine,Zhao, Fei
p. 6414 - 6421
(2020/07/09)

Optimizing ligand structure for low-loading and fast catalysis for alkynyl-alcohol and-amine cyclization
A series of [Ru(Cp/Cp?)(PR2NR′2)(MeCN)]PF6 complexes were prepared, in which the steric and electronic properties of the primary coordination sphere were varied (R = Ph, t-Bu, Bn; and Cp vs. Cp?). These complexes were catalytically active in the cyclization of alkyne substrates with an intramolecular nucleophile (amine or alcohol) to produce 5-and 6-membered heterocycles. The effect of the 1° coordination sphere structure on catalyst performance was evaluated. Steric bulk around the metal centre was a key feature to achieve rapid catalysis at low temperatures. The catalyst [Ru(Cp)(Pt-Bu2NPh2)(MeCN)]PF6 gave a turnover number that was >1 order of magnitude more active than previous catalysts in the cyclization of the benchmark substrate 2-ethynylaniline. This catalyst is tolerant of a diversity of functional groups and is competent at the formation of various substituted indoles.
Stubbs, James M.,Bridge, Benjamin J.,Blacquiere, Johanna M.
p. 7928 - 7937
(2019/06/13)

Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles
Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).
Liu, Tingting,Wu, Kaikai,Wang, Liandi,Yu, Zhengkun
supporting information
p. 3958 - 3964
(2019/08/01)

A indole compound and its preparation method and application (by machine translation)
The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)
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Paragraph 0131; 0156; 0157

(2018/10/02)

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer
Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.
Huang, Yuan-Qiong,Song, Hong-Jian,Liu, Yu-Xiu,Wang, Qing-Min
supporting information
p. 2065 - 2069
(2018/01/27)

Catalyst-free Synthesis of 6-Hydroxy Indoles via the Condensation of Carboxymethyl Cyclohexadienones and Amines
An efficient catalyst-free synthesis of 6-hydroxy indoles from carboxymethyl cyclohexadienones and primary amines has been developed. The aza-Michael addition of the in situ formed enamine, generated through the condensation of carboxymethyl unit of the s
Reddy, Reddy Rajasekhar,Adlak, Komalkant,Ghorai, Prasanta
p. 8426 - 8437
(2017/08/23)

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry
Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.
Ranasinghe, Nadeesha,Jones, Graham B.
p. 1740 - 1742
(2013/04/10)

Convenient modification of the Leimgruber-Batcho indole synthesis: Reduction of 2-nitro-p-pyrrolidinostyrenes by the FeCl3-activated carbon-N2H4H2O system
A new catalytic system containing ferric chloride, activated carbon, and hydrazine has been proposed for the reductive cyclization of β-dialkylamino-2-nitrostyrenes to give the corresponding indoles (Leimgruber-Batcho synthesis). Various substituted indoles may be obtained in high yield under these conditions.
Taydakov,Dutova,Sidorenko,Krasnoselsky
experimental part
p. 425 - 434
(2012/01/13)

INDOLE DERIVATIVES AND DRUGS CONTAINING THE SAME
An indole derivative represented by the following general formula (1) : wherein at least one of R1, R2, R3, and R4 represents an alkoxy group containing 1 to 20 carbon atoms, and other groups of the R1, R2, R3, and R4 represent hydrogen, an alkyl group containing 1 to 6 carbon atoms, acetyl group, or hydroxyl group; and either one of X and Y represents -(CH2)nOH wherein n is an integer of 0 to 30, and the other one of the X and Y represents hydrogen atom; or a salt thereof; and a drug and an agent for promoting differentiation of a stem cell containing such indole derivative or its salt as an effective component. The indole derivative (1) of the present invention has action of inducing differentiation of neural stem cell specifically into a neuron, and this indole derivative is useful as a prophylactic or therapeutic drug for brain dysfunction or neuropathy caused by loss or degeneration of the neuron.
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Page/Page column 9

(2010/02/11)

Effects of indole fatty alcohols on the differentiation of neural stem cell derived neurospheres
In a search for inducers of neuronal differentiation to treat neurodegenerative diseases such as Alzheimer's disease, a series of indole fatty alcohols (IFAs) were prepared, 13c (n = 18) was able to promote the differentiation of neural stem cell derived neurospheres into neurons at a concentration of 10 nM. Analysis of the expression of the Notch pathway genes in neurospheres treated during the differentiation phase with 13c (n = 18) revealed a significant decrease in the transcription of the Notch 4 receptor.
Coowar, Djalil,Bouissac, Julien,Hanbali, Mazen,Paschaki, Marie,Mohier, Eliane,Luu, Bang
p. 6270 - 6282
(2007/10/03)

A simple two-step synthesis of indoles
A two-step synthesis of indoles that is suitable for use on a large scale is described. The general applicability of this methodology has also been briefly explored.
Walkington, Andrew,Gray, Matthew,Hossner, Frank,Kitteringham, John,Voyle, Martyn
p. 2229 - 2233
(2007/10/03)

Ruthenium-catalysed synthesis of indoles from anilines and trialkanolamines in the presence of tin(II) chloride dihydrate
Anilines react with trialkanolamines in dioxane in the presence of a catalytic amount of a ruthenium catalyst together with tin(II) chloride dihydrate to give the corresponding indoles in moderate to good yields.
Cho, Chan Sik,Lim, Hyo Kyun,Shim, Sang Chul,Kim, Tae Jeong,Choi, Heung-Jin
p. 995 - 996
(2007/10/03)

Palladium-Catalyzed Synthesis of Indoles by Reductive N-Heteroannulation of 2-Nitrostyrenes
A palladium-phosphine catalyzed reductive N-heteroannulation of 2-nitrostyrenes, in the presence of carbon monoxide, producing indoles has been developed. Indoles were obtained, in moderate to excellent yield, from substituted 2-nitrostyrenes having either electron-withdrawing (NO2 and CO2-Me) or electron-donating (Br, OH, Me, OMe, and OTf) substituents on the aromatic ring. Best results were obtained using palladium diacetate (6 mol percent) together with triphenylphosphine (24 mol percent) as the catalytic system, under 4 atm of carbon monoxide in acetonitrile at 70 °C. Other palladium(II) and palladium(0) complexes also catalyze the reaction.
So?derberg, Bjo?rn C.,Shriver, James A.
p. 5838 - 5845
(2007/10/03)

Facile synthesis of 6-hydroxyindole and 6-methoxyindole via regioselective Friedel-Crafts acylation and Baeyer-Villiger oxidation
A facile synthesis of 6-hydroxyindole and 6-methoxyindole starting from indole is described. Regioselective chloroacetylation of 1-pivaloylindole followed by Baeyer-Villiger oxidation offers introduction of an oxygen function into the 6-position of the indole ring. Deacylation of 6-chloroacetyl-1-pivaloylindole gives 6-hydroxyindole which is converted to 6-methoxyindole by methylation. The overall yield of 6-hydroxyindole and 6-methoxyindole from indole is 54 and 37%, respectively.
Teranishi,Nakatsuka,Goto
p. 1018 - 1020
(2007/10/02)

Decarboxylation of Indole-2-carboxylic Acids: Improved Procedures
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Jones, Graham B.,Chapman, Brant J.
p. 5558 - 5559
(2007/10/02)

Entry into 6-methoxy-D(+)-tryptophans. Stereospecific synthesis of 1-benzenesulfonyl-6-methoxy-D(+)-tryptophan ethyl ester
A strategy for the synthesis of optically active ring-A methoxylated indole alkaloids which employs the Moody azide/Schollkopf chiral auxiliary protocol has resulted in the successful preparation of 1-benzenesulfonyl-6-methoxy-D(+)-tryptophan ethyl ester 16. This amino ester is required for the synthesis of Alstonia bisindole alkaloids including macralstonine 2 via an enantiospecific Pictet-Spengler reaction
Allen,Hamaker,La Loggia,Cook
p. 2077 - 2102
(2007/10/02)

Palladium-Catalyzed Synthesis of Indoles from 2-Nitrostyrenes
In the presence of palladium salts, oxidation of 2-nitrostyrenes 1 with nitrous acid alkyl esters 2 resulted in the formation of 2-nitrophenylacetaldehyde dialkyl acetals 3.Reductive cyclization of the acetals 3 with iron powder in acetic acid afforded indoles 5 in good yield.
Izumi, Taeko,Soutome, Michihiko,Miura, Takashi
p. 1625 - 1629
(2007/10/02)

Synthesis of camalexin and related phytoalexins
A number of 3-(2′-thiazoyl)indoles, including two recently reported phytoalexins, have been prepared from the Grignard reaction of the corresponding substituted indole and 2-bromothiazole. The antifungal activity of these 3-(2′-thiazoyl)indoles and 3-(2′-oxazolyl)indole have been examined.
Ayer, William A.,Craw, Peter A.,Ma, Yu-Ting,Miao, Shichang
p. 2919 - 2924
(2007/10/02)

Preparation of indoles and oxindoles from N-(tert-butoxycarbonyl)-2-alkylanilines
Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz[c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl)1H-pyrrolo[2,3-b]pyridine (21).
Clark,Muchowski,Fisher,Flippin,Repke,Souchet
p. 871 - 878
(2007/10/02)

A Regiocontrolled Synthesis of Substituted Indoles by Palladium-Catalyzed Coupling of 2-Bromonitrobenzenes and 2-Bromoacetanilides
The palladium-catalyzed cross-coupling reaction of 2-bromonitrobenzenes or 2-bromoacetanilides with ethylene has been used to produce a variety of substituted indoles.The mild reaction conditions and selectivity inherent in the coupling reaction have been utilized to produce regiochemically pure 4-, 5-, 6-, and 7-substituted indoles.
Kasahara, Akira,Izumi, Taeko,Murakami, Satoshi,Miyamoto, Kazuhiro,Hino, Toshimi
p. 1405 - 1413
(2007/10/02)

Reactions of Organic Anions, 147.- Simple and General Synthesis of Hydroxy- and Methoxyindoles via Vicarious Nucleophilic Substitution of Hydrogen
A simple synthesis of 4-, 5-, 6-, and 7-hydroxy- and -methoxyindoles via cyanoalkylation of O-protected nitrophenols by vicarious nucleophilic substitution of hydrogen, followed by catalytic hydrogenation of the (2-nitroaryl)acetonitriles obtained is described.
Makosza, Mieczyslaw,Danikiewicz, Witold,Wojciechowski, Krzysztof
p. 203 - 208
(2007/10/02)

Synthesis of Indole Derivatives from 2-Bromoanilines by a Palladium-assisted Reaction
In the presence of palladium(II) acetate, 2-bromoanilines readily react with enamines such as N-vinylpyrrolidone or α-piperidinostyrene to produce indole derivatives.
Kasahara, Akira,Izumi, Taeko,Kikuchi, Tokio,Xiao-ping Lin
p. 1555 - 1556
(2007/10/02)

SYNTHESIS OF INDOLES FROM N-ARYL-1-ALKENYLSULPHINAMIDES
Reactions of 1-alkenylmagnesium bromides with N-sulphinyl-benzenamines affords the title sulphinamides 5.On heating in toluene, these sulphonamides 5 are the transformed into the corresponding indoles.
Baudin, Jean-Bernard,Julia, Sylvestre A.
p. 837 - 840
(2007/10/02)

Convenient Synthesis of 6-Methoxyindole and 6-Methoxytryptophyl Bromide
A preparatively convenient synthesis of 6-methoxyindole (7) and 6-methoxytryptophylbromide (11) is presented starting with p-cresol (1).Regioselective nitration of p-cresol carbonate (2) followed by hydrolysis of the carbonate and methylation gives 4-methoxy-2-nitrotoluene (5) which is converted to 7 by esterification, reduction and bromination yields 6-methoxytryptophyl bromide (11).The overall yield of 7 and 11 from p-cresol is 43percent and 25percent respectively.
Feldman, Paul L.,Rapoport, Henry
p. 735 - 737
(2007/10/02)

Synthesis of Substituted Indoles via Meerwein Arylation
A new method for the synthesis of substituted indoles is detailed.Meerwein arylation of 4- and 6-substituted 2-nitrobenzenediazonium chlorides with vinyl acetate or vinyl bromide and subsequent reductive cyclization of the resulting adducts affords the corresponding 6- and 4-substituted (CH3, OCH3, Cl, Br, CF3) indoles.The diazonium bisulfates of weakly basic 2-nitroanilines (4-Cl, 6-Br, 4-CF3) gave higher yields of Meerwein arylation adducts than the corresponding diazonium chlorides.Coupling of 2-nitrobenzenediazonium chloride with 2-acetoxy-1-alkenes followed byreductive cyclization affords 2-alkylindoles.
Raucher, Stanley,Koolpe, Gary A.
p. 2066 - 2069
(2007/10/02)

HETEROGENEOUS-CATALYTIC E. FISCHER REACTION XIV. EFFECT OF ELECTRONIC FACTORS IN THE HETEROGENEOUS-CATALYTIC E. FISCHER REACTION
The effect of electronic factors on the heterogeneous-catalytic E.Fischer reaction was studied for the case of methoxy- and nitro-substituted arylhydrazones.It was shown that the presence of the methoxy groups in all probability increases the basicity of the respective hydrazone and facilitates adsorption of the active centers of the catalyst.In this case indoles are obtained with high yields.The presence of nitro groups hinder the adsorption of the hydrazone on the catalyst and as a result leads to a decrease in the yield of indole.
Suvorov, N. N.,Shkil'kova, V. N.,Podkhalyuzina, N. Ya.
p. 2117 - 2120
(2007/10/02)

A SIMPLE PROCEDURE FOR THE PREPARATION OF INDOLES
Indoles are easily prepared in 60-70percent yield from the corresponding o-nitrotoluenes by condensation with tripiperidinomethane, followed by reductive cyclization with aqueous titanous chloride.
Lloyd, David H.,Nichols, David E.
p. 4561 - 4562
(2007/10/02)

Synthesis of 6-Methoxyindoles and Indolines. Regioselective C-6 Bromination of Indolines and Subsequent Nucleophilic Substitution with a Methoxyl Group
Regioselective bromination of the 6-position of indolines was investigated.Treatment of indolines with bromine in sulfuric acid in the presence of silver sulfate or with bromine in superacid afforded the 6-bromoindolines, which were converted to 6-methoxyindolines and indoles.
Miyake, Yuko,Kikugawa, Yasuo
p. 349 - 352
(2007/10/02)

HETEROGENEOUS-CATALYTIC FISCHER REACTION. 13. CATALYTIC SYNTHESIS OF 4-, 5-, 6-, AND 7-METHOXYINDOLES
Methoxy-substituted acetaldehyde phenylhydrazones were cyclized in the vapor phase on GIPKh-115 catalyst to give 4-, 5-, 6-, and 7-methoxyindoles. 5-Methoxyindole was obtained in 50percent yield, 4- and 6-methoxyindoles were obtained in 85percent yield, and 7-methoxyindole was obtained in 45percent yield.
Suvorov, N. N.,Shkil'kova, V. N.,Podkhalyuzina, N. Ya.
p. 802 - 803
(2007/10/02)

SYNTHESIS OF INDOLES FROM N-(TRIFLUOROACETYL)-2-ANILINO ACETALS
N-(trifluoroacetyl)indoles (3) are produced in high yield from appropriately ring-substituted N-(trifluoroacetyl)-2-anilino acetals (2) in boiling trifluoroacetic acid containing excess trifluoroacetic anhydride.Mild saponification provides the free indoles nearly quantitatively.The scope of the reaction is discussed.The ring closure follows solvolytic substitution of a trifluoroacetoxy group for one of the ethoxy groups in 2.The method has been extended to cyclization of N-(trifluoroacetyl)-α-anilinoacetone in hot polyphosphoric acid followed by saponification to yield 3-methylindole.
Nordlander, J. Eric,Catalane, David B.,Kotian, Kirtivan D.,Stevens, Randall M.,Haky, Jerome E.
p. 778 - 782
(2007/10/02)

Intermediates for indoles
Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.
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(2008/06/13)