10604-59-8Relevant articles and documents
Pyrazolo[4,3-a]quinindoline as a new highly fluorescent heterocyclic system: Design, synthesis, spectroscopic characterization and DFT calculations
Alikhani, Elaheh,Pordel, Mehdi,Daghigh, Leila Rezaei
, p. 1484 - 1490 (2015)
(Chemical Equation Presented) After obtaining the desired precursors in several reactions, new N-alkyl-substituted heterocyclic system pyrazolo[4,3-a]quinindolines (pyrazolo[4,3-f]-indolo[2,3-b]quinolines) were synthesized by one-pot reaction of 1-alkyl-5-nitro-1H-indazole with 2-(1-alkyl-1H-3-indolyl)acetonitrile in MeOH/KOH solution via the nucleophilic substitution of hydrogen in excellent yields. Spectral (UV-Vis, FT-IR, NMR and fluorescence) and analytical data allowed the structures of the synthesized compounds to be established. The values of absorption and fluorescence maxima, extinction coefficients and fluorescence quantum yield of these new heterocyclic fluorophores were obtained and they show highlighting interesting photophysical properties. Density functional theory (DFT) calculations of one structure by using the B3LYP hybrid functional and the 6-311 + G(d,p) basis set were performed to provide the optimized geometry, relevant frontier orbitals and the prediction of 1H NMR chemical shifts. Calculated electronic absorption spectrum of one structure was also obtained by time-dependent density functional theory (TD-DFT) method. Solvatochromic properties of these dyes have been discussed and the results showed that the absorption and emission bands in polar solvents undergo a modest red shift.
ALKYLATIONS EN ABSENCE DE SOLVANT ORGANIQUE. EFFETS D'ADDITION D'OXYDES MINERAUX ET DE SELS D'AMMONIUM - I. N-ALKYLATION DE L'INDOLE EN MILIEU BASIQUE
Barry, J.,Bram, G.,Decodts, G.,Loupy, A.,Pigeon, P.,Sansoulet, J.
, p. 2669 - 2672 (1983)
Indole alkylation, after anion formation (KOH+1percent NBu4Br) is achieved without any solvent in the presence or in the absence of solid mineral supports.N-Ethyl or octyl derivatives are thus obtained quantitatively under very mild conditions.
Cascade oxidative dearomatization/semipinacol rearrangement: An approach to 2-spirocyclo-3-oxindole derivatives
Peng, Jin-Bao,Qi, Yue,Ma, Ai-Jun,Tu, Yong-Qiang,Zhang, Fu-Min,Wang, Shao-Hua,Zhang, Shu-Yu
, p. 883 - 887 (2013)
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Gray et al.
, p. 1939,1942 (1960)
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Palladium catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives
Wu, Yongcheng,Peng, Xiaopeng,Luo, Bingling,Wu, Fuhai,Liu, Bo,Song, Fenyun,Huang, Peng,Wen, Shijun
, p. 9777 - 9780 (2014)
Palladium(ii)-catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums was successfully achieved, providing a concise method to synthesize dibenzocarbazoles. In a single operation, two C-C bonds and one ring were formed. The reaction was ligand free and tolerated air and moisture conditions.
Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions
Raina, Gaurav,Kannaboina, Prakash,Mupparapu, Nagaraju,Raina, Sushil,Ahmed, Qazi Naveed,Das, Parthasarathi
, p. 2134 - 2147 (2019)
Transition-metal-catalyzed programmed sequential arylation reactions of 2-chloro-4-nitro-1H-imidazoles were achieved. The methods are general and were applied in a chemoselective manner for the synthesis of different multiarylated 4-nitroimidazoles bearing three different aryl groups. A salient feature is Pd-catalyzed hetero-hetero coupling at the C5 position through a NO2 directed cross-dehydrogenative coupling (CDC) approach.
Phase-Transfer Alkylation of Heterocycles in the Presence of 18-Crown-6 and Potassium tert-Butoxide
Guida, Wayne C.,Mathre, David J.
, p. 3172 - 3176 (1980)
It has been found that the N-alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen can be accomplished in diethyl ether via a phase-transfer process in which 18-crown-6 is employed as the catalyst and potassium tert-butoxide is employed as the base.In this manner, pyrrole (1), indole (2), pyrazole (3), imidazole (4), benzimidazole (5), benzotriazole (6), carbazole (7), and methyl indole-3-acetate (8) can be successfully alkylated.The procedure is convenient and mild and generally gives rise to exclusive N-alkylation.
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Rubottom,Chabala
, p. 566 (1972)
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N-Alkylation of Pyrrole, Indole, and Several Other Nitrogen Heterocycles Using Potassium Hydroxide as a Base in the Presence of Polyethylene Glycols or Their Dialkyl Ethers
Sukata, Kazuaki
, p. 280 - 284 (1983)
The alkylation of pyrrole and indole in aqueous potassium hydroxide-organic two-phase systems in the presence of polyethylene glycols (PEG) or their dialkyl ethers (PEG-ether) as phase transfer catalysts (PTC) gave substantial quantities of the C-alkylated and C,N-polyalkylated products as well as the N-alkylated products.This fact is similar to that obtained in the presence of quaternary ammonium salts as PTC.In powdered potassium hydroxide-organic two-phase system, the yields of the N-alkylated products were generally high.Especially, when PEG-ether were employed as solvents, the N-alkylated products were obtained in excellent yields under mild conditions.Imidazole, benzimidazole, carbazole, 2-methylindole, and benzotriazole were similarly N-alkylated in high yields by this method.
Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes
Górski, Krzysztof,Mech-Piskorz, Justyna,Le?niewska, Barbara,Pietraszkiewicz, Oksana,Pietraszkiewicz, Marek
, p. 4672 - 4681 (2020)
The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[b]heteroole 15. Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.
Ruthenium Complex Catalyzed N-Heterocyclization. Syntheses of Quinolines and Indole Derivatives from Aminoarenes and 1,3-Propanediol of Glycols
Tsuji, Yasushi,Huh, Keun-Tae,Watanabe, Yoshihisa
, p. 1673 - 1680 (1987)
Aniline reacts with 1,3-propanediol under reflux in diglyme with spontaneous hydrogen evolution in the presence of a catalytic amount of ruth enium trichloride hydrate ( RuCl3*nH2O)-tributylphosphine (PBu3) to give quinoline in good yield.The yield of quinoline was markedly affected by the molar ratios of aniline to 1,3-propanediol and PBu3 to RuCl3*nH2O.The best yield (76percent) was achieved at the molar ratios of 2.5 of aniline / 1,3-propanediol and 2.0 of PBu3 / RuCl3*nH2O.Also, N-substituted anilines react with ethylene glycol in the presence of a catalytic amount of dichlor otris(triphenylphosphine)ruthenium (RuCl2(PPh3)3) to give N-substituted indole derivatives.The reactions were carried out at 180 deg C in dioxane with spontaneus hydrogen evolution.Aminoarenes also react with 2,3-butanediol and 1,2-cyclohexanediol ( mixture of cis and trans ) in the presence of RuCl2(PPh3)3 to give the corresponding 2,3-dimethylindoles and 1,2,3,4-tetrahydrocarbazoles in good to excellent yields.As the key intermediates of the reactions, N,N'-diarylpropylenediamine (5a) and N,N'-diarylethylenediamine (5b) and their dehydrogenated imine derivatives are postulated.
Regioselective 2-alkylation of indoles with α-bromo esters catalyzed by Pd/P,P=O system
Tian, Wei,Li, Bowen,Tian, Duanshuai,Tang, Wenjun
supporting information, p. 197 - 200 (2021/08/13)
A palladium-catalyzed 2-alkylation of indoles with α-bromo esters is developed by employing a P,P=O ligand. The method features excellent regioselectivities, mild reaction conditions, and good functional group compatibility. The employment of the P,P=O ligand as well as 4? molecular sieves were crucial for the success of the transformation. Mechanistic studies indicate the reaction proceed through a radical pathway.
Application of biomass-supported copper-catalyzed three-component reaction in preparation of fluorine-containing drugs
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Paragraph 0066-0068, (2021/09/29)
The invention relates to an application of a biomass-supported copper-catalyzed three-component reaction in preparation of a fluorine-containing drug. The indole and its derivatives and are synthesized 3 - (2 - (trifluoromethyl) - indo -3 -yl) quinoxaline -2 - ketone derivatives by one-pot synthesis by three-component one-pot method. To the invention, the heterogeneous biological substance carried copper catalyst is adopted to catalyze the reaction, and the problems that a traditional homogeneous catalyst cannot be recovered, metal residues are left and the like are solved. 3 - (2 - (Trifluoromethyl) - indo -3 -yl) quinoxaline -2 - ketone compounds with different substituents are expanded, and the biomass supported copper catalyst can be cyclically and catalytically reacted.
Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents
Matsuo, Kasumi,Kuriyama, Masami,Yamamoto, Kosuke,Demizu, Yosuke,Nishida, Koyo,Onomura, Osamu
, p. 4449 - 4460 (2021/08/25)
The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.
