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.
Propargylamines in Pd/Cu-catalyzed tandem coupling-cyclization-N-deprotection in a single pot: Construction of N-unsubstituted vs N-sulfonyl indole ring
Sujeevan Reddy, Gangireddy,Sandeep Kumar, Jetta,Thirupataiah,Amirul Hossain, Kazi,Babu Nallapati, Suresh,Bhat Giliyaru, Varadaraj,Chandrashekhar Hariharapura, Raghu,Gautham Shenoy,Pal, Manojit
supporting information, (2021/06/18)
The Pd/Cu-catalyzed tandem coupling–cyclization-N-deprotection in a single pot (Method a) vs sequential coupling–cyclization under similar conditions (Method b) has been studied using propargylamine as a terminal alkyne under environmentally friendly cond
Activities of quinoxaline, nitroquinoxaline, and [1,2,4]triazolo [4,3-a]quinoxaline analogs of mmv007204 against schistosoma mansoni
Debbert, Stefan L.,Hintz, Mikaela J.,Bell, Christian J.,Earl, Kenya R.,Forsythe, Grant E.,H?berli, Cécile,Keiser, Jennifer
supporting information, (2021/03/04)
The reliance on one drug, praziquantel, to treat the parasitic disease schistosomiasis in millions of people a year shows the need to further develop a pipeline of new drugs to treat this disease. Recently, an antimalarial quinoxaline derivative (MMV007204) from the Medicines for Malaria Venture (MMV) Malaria Box demonstrated promise against Schistosoma mansoni. In this study, 47 synthesized compounds containing quinoxaline moieties were first assayed against the larval stage of this parasite, newly transformed schistosomula (NTS); of these, 16 killed over 70% NTS at 10mM. Further testing against NTS and adult S. mansoni yielded three compounds with 50% inhibitory concentrations (IC50s) of#0.31mM against adult S. mansoni and selectivity indices of$8.9. Administration of these compounds as a single oral dose of 400mg/kg of body weight to S. mansoni-infected mice yielded only moderate worm burden reduction (WBR) (9.3% to 46.3%). The discrepancy between these compounds' good in vitro activities and their poor in vivo activities indicates that optimization of their pharmacokinetic properties may yield compounds with greater bioavailabilities and better antischistosomiasis activities in vivo.
