243-59-4Relevant articles and documents
The Condensation of Isatin with o-Phenylenediamine
Niume, Kazuma,Kurosawa, Shigeru,Toda, Fujio,Hasegawa, Masaki,Iwakura, Yoshio
, p. 2293 - 2294 (1982)
The condensation of isatin with o-phenylenediamine has been studied in various kind of solvents.The reaction gave pure indoloquinoxaline (1) in acidic solvents, while it gave a mixture containing at least two out three compounds, 1, an anil and a spiro compound, in neutral or basic organic solvents.The anil and spiro compounds were converted to 1 in the presence of acid or by heating them above their melting points.The mechanism of the formation of these compounds and the conversion could be explained by the presence of the intermediate of the adduct formed between the amino groups of o-phenylenediamine and the β-carbonyl of isatin.
β-cyclodextrin mediated synthesis of indole derivatives: reactions of isatins with 2-amino(or 2-thiole)anilines by supramolecular catalysis in water
Shivhare, Km Neha,Siddiqui
, p. 52 - 61 (2019)
An elegant, mild, and straightforward strategy for the synthesis of indole derivatives have been accomplished by the biomimetic catalysis for the first time in water under neutral conditions. This supramolecular catalyst oriented methodology provides a sustainable and green protocol for the synthesis of 6H-indolo[2,3-b]quinoxalines and 3H-spiro[benzo[d]thiazole-2,3’-indolin]-2’-one by the reaction of isatin derivatives with 1,2-difunctionalized benzene using β-cyclodextrin (β-CD) as a recoverable and reusable supramolecular catalyst.
Preparation and structure of tetrakis(indolo[2,3-b]quinoxalinato)dinickel(II)
Takekuma, Shin-Ichi,Katayama, Satoshi,Takekuma, Hideko
, p. 614 - 615 (2000)
Treatment of 6H-indolo[2,3-b]quinoxaline (1) with NaBH4 in ethanol at 82 °C for 10 min under argon gives the reactive anion species 2 (generated by deprotonation of N-6 position of 1), which upon reaction with Ni(OAc)2·4H2O in ethanol at 82 °C for 6 h under argon forms the title dinuclear nickel(II) complex 3. The molecular structure of the novel complex 3, indicating the Ni-Ni distance of 2.618(1) A, is reported.
3-Oxo 3H-Indole from Dioxygen Copper-Catalyzed Oxidation of Indole: One-Flask Synthesis of 2-Dialkylamino 3-Oxo 3H-Indoles.
Capdevielle, Patrice,Maumy, Michel
, p. 2953 - 2956 (1993)
Cu(I)Cl-catalyzed oxidation of indole 1 by dioxygen in anhydrous acetonitrile leads to highly reactive 3-oxo 3H-indole 2, which provides directly 2-dialkylamino 3-oxo 3H-indoles 3 in presence of dialkylamines.Amidines 3, previously difficult to prepare, are potentially useful synthons in the field of heterocyclic chemistry. Key Words: Copper-catalyzed oxidation; dioxygen; indole; 2-dialkylamino 3-oxo 3H-indoles.
One-Pot Construction of Indolo[2,3- b]quinoxalines through Ruthenium-Catalyzed Ortho C-H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides
Laru, Sudip,Bhattacharjee, Suvam,Ghosh, Sumit,Hajra, Alakananda
, p. 7624 - 7629 (2021/10/12)
The synthesis of N-substituted indolo[2,3-b]quinoxalines has been developed through a Ru(II)-catalyzed ortho C-H functionalization of 2-arylquinoxalines with sulfonyl azides and further oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in one pot. This double C-N bond formation strategy provides a new efficient route for the preparation of a series of biologically relevant 6H-indolo[2,3-b]quinoxaline derivatives in up to 94% yield, suggesting a broad substrate scope applicability. The preliminary mechanistic studies reveal that the sequential C-N bond formations proceed through the formation of a five-membered ruthenacyclic intermediate in the first step and a radical mechanism in the second step.
Br?nsted acid hydrotrope combined catalysis in water: a green approach for the synthesis of indoloquinoxalines and bis-tetronic acids
Kumbhar, Arjun,Kanase, Dhanaji,Mohite, Suhas,Salunkhe, Rajshri,Lohar, Trushant
, p. 2263 - 2278 (2021/03/31)
The present work describes the applications of Br?nsted acid hydrotrope combined catalyst (BAHC) as a mild, efficient and reusable catalyst for synthesis of indoloquinoxalines and bis-tetronic acids in water. Using BAHC, we synthesized many indoloquinoxal
