4676-99-7Relevant academic research and scientific papers
An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
supporting information, p. 9610 - 9616 (2021/12/09)
We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
NaNO2/K2S2O8-mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3-Nitro- and 3-Nitrosoindoles
Shoberu, Adedamola,Li, Cheng-Kun,Tao, Ze-Kun,Zhang, Guo-Yu,Zou, Jian-Ping
supporting information, p. 2255 - 2261 (2019/04/13)
JPZ acknowledges financial support from the National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749). (Figure presented.).
Tert-Butyl Nitrite Mediated Synthesis of Fluorinated O-Alkyloxime Ether Derivatives
Ma, Xingxing,Song, Qiuling
, p. 7375 - 7379 (2019/09/30)
A tert-butyl nitrite (TBN)-mediated synthesis of fluorinated O-alkyloxime ether derivatives with bromodifluoroalkyl reagents as the fluorine sources has been developed. A variety of halodifluorinated compounds were found compatible, delivering the desired
Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
supporting information, p. 3527 - 3530 (2018/06/26)
A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones
Mo, Xue-Ling,Chen, Chun-Hua,Liang, Cui,Mo, Dong-Liang
, p. 150 - 159 (2017/11/28)
A variety of (E)-N-aryloxindole nitrones were prepared in good to excellent yields by using a copper-catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)-oxindole nitrones. This method to prepare (E)-N-aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone-derived oxindole nitrone in high yield.
Cyclopalladation of 3-methoxyimino-2-phenyl-3H-indoles
López, Concepción,González, Asensio,Moya, Carlos,Bosque, Ramon,Solans, Xavier,Font-Bardía, Mercè
, p. 2877 - 2886 (2008/12/21)
The direct cyclopalladation of 3-methoxyimino-2-(4-chlorophenyl)-3H-indole (1a) and 3-methoxyimino-2-phenyl-3H-indole (1b) results in the regioselective activation of the ortho σ[C(sp2, phenyl)-H] bond affording (μ-OAc)2[Pd{κ2-C,N-C6H3-4R-1-(C8H4N-3′-NOMe)}]2 (2) {R = Cl (2a) or H (2b)} that contain a central Pd(μ-OAc)2Pd core. Compounds 2a and 2b reacted with triphenylphosphine (in a molar ratio PPh3:2 = 2) giving [Pd{κ2-C,N-C6H3-4R-1-(C8H4N-3′-NOMe)}(OAc)(PPh3)] (3) {R = Cl (3a) or H (3b)}. Treatment of 2a or 2b with a slight excess of LiCl in acetone produced the metathesis of the bridging ligands and the formation of (μ-Cl)2[Pd{κ2-C,N-C6H3-4R-1-(C8H4N-3′-NOMe)}]2 (4) {R = Cl (4a) or H (4b)} with a central Pd(μ-Cl)2Pd moiety. The reactions of 4a or 4b with deuterated pyridine (py-d5) or triphenylphosphine gave the monomeric derivatives [Pd{κ2-C,N-C6H3-4R-1-(C8H4N-3′-NOMe)}Cl(L)] with R = Cl or H and L = py-d5 (5) or PPh3 (6). The crystal structure of 6b·1/2CH2Cl2 confirmed the mode of binding of the ligand, the nature of the metallated carbon atom and a trans-arrangement of the phosphine ligand and the heterocyclic nitrogen. Theoretical calculations on the free ligands are also reported and have allowed the rationalization of the regioselectivity of the cyclopalladation process.
Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent
Astolfi, Paola,Panagiotaki, Maria,Rizzoli, Corrado,Greci, Lucedio
, p. 3282 - 3290 (2008/09/17)
The reaction of 2-phenyl- and 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene leads mainly to the formation of the isonitroso and 3-nitroso indole derivatives, respectively. When reacted
N-nitrosodiphenylamine as an alternative nitrosating agent for indoles
Cardellini,Greci,Stipa
, p. 677 - 682 (2007/10/02)
N-nitrosodiphenylamine reacts in the presence of catalytic amounts of trichloroacetic acid with indoles forming the corresponding nitroso and isonitroso derivatives in good yields.
3--2-phenyl-3H-indole; A New Convenient Spin Label
Chiorboli, Elena,Greci, Lucedio
, p. 219 - 220 (2007/10/02)
The reaction of 3-chlorocarbonyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-1-oxyl with 3-oximino-2-phenyl-3H-indole in aqueous sodium hydroxide affords 3--3H-indole.This nitroxyl does not u
Direct Acting, Highly Mutagenic, α-Hydroxy N-Nitrosamines from 4-Chloroindoles
Buechi, George,Lee, Gary C. M.,Yang, David,Tannenbaum, Steven R.
, p. 4115 - 4119 (2007/10/02)
Fave beans (Vicia fava) contain 4-chloro-6-methoxyindole, a promutagen, which on nitrosation under simulated gastric conditions forms 4-chloro-6-methoxy-2-hydroxy-N1-nitrosoindolin-3-one oxime, a direct-acting, exceedingdly potent, mutagen whic
