23073-34-9Relevant academic research and scientific papers
Reactivity of the acids of trivalent phosphorus and their derivatives. Part X. Unexpected reactivity of the >P-O- anions toward 2-phenyl-3-phenyliminoindolenine N-oxide
Przychodzeń, Witold,Konitz, Antoni,Wojnowski, Wies?aw,Rachon, Janusz
, p. 21 - 39 (1998)
The reaction of the >P-O- reagent with 2-phenyl-3-phenyliminoindolenine N-oxide 1 gave reduction product, namely 2-phenyl-3-phenylimino-3H-indole 2. Dialkyl phosphites undergo nucleophilic addition into endo C=N double bond of the 2-phenyl-3-phenyl-imino-3H-indole 2 to furnish dialkyl 2-phenyl-3-phenylimino-2-indolinephosphonate 3. The structure of the aminophosphonate 3 was established by X-ray crystallography.
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
New insights on the reaction of trialkyl phosphites with 2-phenyl-3-phenylimino-3H-indole N-oxide: An indolic nitrone. Crystal structures of 1-diethylphosphoryl-2-phenyl-3-phenylamino-1H-indole and 2-phenyl-4-phenylimino-4H-3,1-benzoxazine
Canestrari, Stefania,Mar'in, Alexander,Sgarabotto, Paolo,Righi, Lara,Greci, Lucedio
, p. 833 - 838 (2007/10/03)
2-Phenyl-3-phenylimino-3H-indole N-oxide (an indolic nitrone) reacts with triethyl and triisopropyl phosphite in refluxing xylene and tert-butylbenzene to give 2-phenyl-3-phenylimino-3H-indole (indolenine) in very good yield. The same reaction carried out in refluxing phosphite gave rise to a series of compounds which in part derive from the thermal rearrangement of the starting nitrone and in part from the interaction of the indolenine with phosphites. The formation of the products arising from the reduction of the indolenine is explained by an electron transfer process between this intermediate and the phosphite; whereas the formation of the phosphorylated products is interpreted through the evolution of the intermediate zwitterion generated by the nucleophilic attack of the phosphite on carbon-2 of the indolenine. The formation of this intermediate is also discussed in terms of an electron transfer process. Crystal structures of 1-diethylphosphoryl-2-phenyl-3-phenylamino-1H-indole and 2-phenyl-4-phenylimino-4H-3,1-benzoxazine are also described.
Reactivity of the acids of trivalent phosphorus and their derivatives. Part X*. Unexpected reactivity of the >P-O- anions toward 2-phenyl-3-phenyl-iminoindolenine N-oxide
Przychodzen, Witold,Konitz, Antoni,Wojnowski, Wieslaw,Rachon, Janusz
, p. 211 - 230 (2007/10/03)
The reaction of the >P-O- reagent with 2-phenyl-3-phenyliminoindolenine N-oxide 1 gave a reduction product, namely 2-phenyl-3-phenylimino-3H-indole 2 . Dialkyl phosphites undergo nucleophilic addition into the endo C=N double bond of the 2-phenyl-3-pnenylimino-3H-indole 2 to furnish dialkyl 2-phenyl-3-phenylimino-2-indolinephosphonate 3. The structure of the aminophosphonate 3 was established by X-ray crystallography.
DIRECT AMINATION. Part 4. REACTIONS OF INDOLES WITH PRIMARY AROMATIC AMINES AND IODOSOBENZENE DIACETATE
Cardellini, Liberato,Greci, Lucedio,Maurelli, Eziana,Orena, Mario,Stipa, Pierluigi,Tosi, Giorgio
, p. 1917 - 1926 (2007/10/02)
Indole, 2-methylidole, 2-phenylindole, and primary aromatic amines react with iodosobenzene diacetate leading both to 2-arylamino-3-arylimino-3H-indole in the case of indole and 2-methylindole, and to 2-phenyl-3-arylimino-3H-indole in the case of 2-phenylindole.The reaction is believed to proceed through the formation of a nitrenium ion formed by the interaction of iodosobenzene diacetate and primary aromatic amines and the mechanism is supported by experimental evidences.The methyl elimination from 2-methylindole is explained on the basis of the isolation of the possible intermediate and the formation of an animal, whose decomposition leads to the reaction products.The intermediate animal is proposed on the basis of the bis-(2-methylindol-3-yl)methane formation.
Direct Amination. Part 2. Reaction of 2-Phenylindole with Primary Aromatic Amines. A Chemical and Electrochemical Investigation
Berti, Corrado,Greci, Lucedio,Andruzzi, Romano,Trazza, Antonio
, p. 607 - 610 (2007/10/02)
The reaction of 2-phenylindole with primary aromatic amines to form 2-phenyl-3-arylimino-3H-indoles, in the presence of N-chlorobenzotriazole, N-chloroisatin or lead tetraacetate, were also investigated by anodic oxidation.The chemical and electrochemical results suggest a mechanism involving an intermediate nitrenium ion, whose formation was demonstrated by an independent route.The reaction of 1-hydroxy-2-phenylindole with p-anisidine to form 2-phenyl-3-p-methoxyphenylimino-3H-indole 1-oxide, previously studied under anodic oxidation is here described in the presence of N-chlorobenzotriazole.
