Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine

Bergman, Jan; Engqvist, Robert; Stålhandske, Claes; Wallberg, Hans

doi:10.1016/s0040-4020(02)01647-2

Cited by 97 publications

(64 citation statements)

References 43 publications

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“…Synthesis The preparations of the 11-chloro-6-methyl-6H-indolo[2,3-b] quinolines 6 were carried out according to the method reported by Bergman et al 24) and us. [25][26][27] Thus, as shown in Chart 1, the reaction of indole-3-carboxylate 1a and 4-chloroaniline (2) using N-chlorosuddinimide (NCS) as a coupling reagent formed the 2-anilinoindole-3-carboxylate 3a.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in Vitro Testing of Antimalarial Activity of Non-natural-Type Neocryptolepines: Structure–Activity Relationship Study of 2,11- and 9,11-Disubstituted 6-Methylindolo[2,3-b]quinolines

et al. 2013

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This report describes the synthesis and in vitro anti-malarial evaluations of certain C2 or C8 and C11-disubstituted 6-methyl-5H-indolo[2,3-b]quinoline (neocryptolepine congener) derivatives. To attain higher activities, the structure-activity relationship (SAR) studies were conducted by varying the kind of alkylamino or ω-aminoalkylamino stubstituents at C11 and with Cl at the C2 position, or CO 2 Me at the C9 position. The anti-malarial activities of the tested compounds were significantly increased compared to the 11-non(alkylamino) derivatives. The 3-aminopropylamino group at C11 was further modified to urea and thiourea, which improved the cytotoxicity against normal cells. The best results were achieved with compounds 8 and 9d against the NF54 strain with the IC 50 /SI values as of 86 nM/20 and 317 nM/370, respectively. Furthermore, the compounds were tested for β-haematin inhibition. Twelve were found to have IC 50 values below 100 µM and a linear correlation between the β-haematin inhibition and cell growth inhibition in the NF54 strain was found for those derivatives with basic amino side chains. A second correlation was identified between the NF54 activity and physico-chemical factors related to solvation and polarity.

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Section: Resultsmentioning

confidence: 99%

Synthesis and in Vitro Testing of Antimalarial Activity of Non-natural-Type Neocryptolepines: Structure–Activity Relationship Study of 2,11- and 9,11-Disubstituted 6-Methylindolo[2,3-b]quinolines

et al. 2013

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“…The condensation of isatin derivatives with o-phenylenediamine gives three different products (Bergman et al, 2003;Ivashchenko et al, 1984;Niume et al, 1982) depending on the reaction conditions, so the formation of selectively one of the product was our prime objective and that was achieved by using TiO 2 NPs catalyst under solvent free conditions. Condensation reaction of isatin derivatives 1a-m with o-phenylenediamine 2 in the presence of catalytic amount of TiO 2 NPs under solvent-free conditions at 100°C, afforded selectively quinoxaline derivatives 3a-m in excellent yield (Scheme 1 and Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…There are several methodologies reported in the literature for the condensation reaction of isatin and substituted isatins with o-phenylenediamine (Alsubari et al, 2009;Bergman et al, 2003;Ivashchenko et al, 1984;Niume et al, 1982). These protocols suffer from shortcomings such as mixture of products, prolonged reaction time, low yields, harsh reaction conditions, undesirable by products and toxicity.…”

Section: Introductionmentioning

confidence: 99%

Rutile phase nanoTiO2 as an effective heterogeneous catalyst for condensation reaction of isatin derivatives with 1,2-diaminobenzene under solvent free conditions: A greener “NOSE” approach

Bajpai

Singh

Srivastava

2019

Arabian Journal of Chemistry

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Rutile phase of TiO 2 nanoparticles were readily prepared and identified as an efficient heterogeneous catalyst for the synthesis of a library of quinoxaline derivatives by condensation reaction of isatin derivatives with o-phenylenediamine under solvent-free conditions. The presented method is mild, environmentally friendly, inexpensive and highly effective to give the products in good to excellent yields. The recyclability of the catalyst is another emphasis of proposed methodology. ª 2014 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).

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“…12 Thus, the reactions proceeded in very good to excellent yields with complete chemo-and regioselectivity giving rise to compounds 3 in the presence of anilines bearing either electron-donating or electron-withdrawing groups ( Table 2, entries 1-3, 5-7, 11-13). Only the reactions performed on 2-alkynylindole 2g gave the corresponding pyrimido[1,6-a]indol-1-ones 3o-p in very low yields (Table 2, entries 15,16). In this case, beside the desired com-…”

Section: Figurementioning

confidence: 96%

Novel Domino Approach to Fluorescent Pyrimido[1,6-a]indolones

Facoetti¹,

Abbiati²,

d’Avolio³

et al. 2009

Synlett

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Easily accessible N-ethoxycarbonyl-2-alkynylindoles undergo, in the presence of primary aryl amines and under TiCl 4 / t-BuNH 2 catalysis, domino hydroamination-annulation reactions giving rise to pyrimido [1,6-a]indolones in good to excellent yields. The reaction involves an initial highly regio-and chemoselective hydroamination reaction. The obtained compounds show interesting fluorescence properties and could represent a new class of useful markers for bioanalytical purpose.Domino reactions are now widely used to assemble simple or polyfunctionalized organic molecules. 1 Thus, domino reactions allow the formation of several new covalent bonds in a one-pot fashion, can accomplish the coupling of three or more simple building blocks in a modular approach, and, in several cases, match well also with Trost's atom-economy concept. 2 Moreover, they offer an attractive, economical, and ecologically benign alternative to classical organic transformations. In this context, transition-metal catalysis has proven to play a pivotal role for the direct construction of complicated heterocyclic and heteropolycyclic molecules from readily accessible starting materials under mild conditions. During the last years, we focused our attention on the catalyzed and uncatalyzed domino addition-annulation reactions of 2-acyl-N-propargylindoles and 2-acyl-3-alkynyl(or propargyl)indoles for the synthesis of a-or bfused polycyclic indole systems, respectively. Thus, using this synthetic approach, b-carbolines, 3 pyrazino[1,2-a]-indoles, 4 [1,4]oxazino[4,3-a]indoles, 5 pyrrolo[1,2-a]indol-2-carbaldehydes, 6 1-aminocarbazoles, 7 and 9-amino-pyrido[1,2-a]indoles 7 have been obtained. Most of the reported reactions 3-5,7 involve in the second step, step b of the domino reaction, a nucleophilic attack onto a carbon-carbon triple bond that allows the annulation onto an existing ring (Figure 1, A). Furthermore, we reversed the sequence by performing a domino reaction involving in the first step, step a, a TiCl 4 /t-BuNH 2 -catalyzed hydroamination of the carbon-carbon triple bond followed by nucleophilic attack of the enamine intermediate at the carbon-oxygen double bond (Figure 1, B). 6 Figure 1During recent years, catalyzed hydroamination reactions became a valuable tool for the synthesis of nitrogen heterocycles and complex molecules. 8 Among various catalysts employed, titanium-based catalysts are particularly attractive in terms of costs, functional group tolerability, and regioselectivities. 9 In particular, the inexpensive and user-friendly TiCl 4 /t-BuNH 2 catalytic system has been described for the regioselective intermolecular antiMarkovnikov hydroamination of alkynes. 10 N-Ethoxycarbonyl-2-alkynylindoles 2a-g were synthesized in excellent yields starting from 2-trifluoromethanesulfonyloxy-indole-1-carboxylic acid ethyl ester (1) and terminal alkynes following the Sonogashira protocol (Table 1). 11On these bases, we investigated a domino sequence involving hydroamination-annulation of N-ethoxycarbonyl-2-alkynylindoles with primary amin...

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Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine

Cited by 97 publications

References 43 publications

Synthesis and <i>in Vitro</i> Testing of Antimalarial Activity of Non-natural-Type Neocryptolepines: Structure–Activity Relationship Study of 2,11- and 9,11-Disubstituted 6-Methylindolo[2,3-<i>b</i>]quinolines

Synthesis and <i>in Vitro</i> Testing of Antimalarial Activity of Non-natural-Type Neocryptolepines: Structure–Activity Relationship Study of 2,11- and 9,11-Disubstituted 6-Methylindolo[2,3-<i>b</i>]quinolines

Rutile phase nanoTiO2 as an effective heterogeneous catalyst for condensation reaction of isatin derivatives with 1,2-diaminobenzene under solvent free conditions: A greener “NOSE” approach

Novel Domino Approach to Fluorescent Pyrimido[1,6-a]indolones

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