Synthesis of Some New Heterocyclic Compounds Containing Indole Moeity

Sayed, Mostafa; El‐Dean, Adel M. Kamal; Ahmed, Mostafa; Hassanien, Reda

doi:10.17628/ecb.2017.6.171-176

Cited by 8 publications

(6 citation statements)

References 7 publications

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“…Synthesis of Schiff Bases. As shown in Scheme 1, the starting material 3-chloro-1H-indole-2-carbaldehyde (1) was prepared according to the previously published procedure, 50 which then was allowed to react with different aromatic amines represented in 4-anisdine, 4-aminoacetophenone, 1-naphthyl amine, and 6-aminonaphthalene-2-sulfonic acid in the presence of piperidine as a homogeneous catalyst. The reaction mixture was refluxed for ≥ 4 h, and the used solvent was ethanol.…”

Section: Resultsmentioning

confidence: 99%

“…All the Schiff base derivatives were synthesized by refluxing an ethanolic solution of 3-chloro- 1H -indole-2-carbaldehyde ( 1) (6 mmol, 0.5 gm) and the corresponding aromatic or heterocyclic amine (6 mmol) in 1:1 stoichiometric ratio for the mentioned time in the presence of piperidine catalyst (five drops). ,, The solid precipitate formed after cooling the reaction mixture was filtered off, dried, and recrystallized from ethanol to afford the desired pure compounds.…”

Section: Methodsmentioning

confidence: 99%

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Base-Free Synthesis and Photophysical Properties of New Schiff Bases Containing Indole Moiety

et al. 2022

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Schiff bases represent an essential class in organic chemistry with antitumor, antiviral, antifungal, and antibacterial activities. The synthesis of Schiff bases requires the presence of an organic base as a catalyst such as piperidine. Base-free synthesis of organic compounds using a heterogeneous catalyst has recently attracted more interest due to the facile procedure, high yield, and reusability of the used catalyst. Herein, we present a comparative study to synthesize new Schiff bases containing indole moieties using piperidine as an organic base catalyst and Au@TiO 2 as a heterogeneous catalyst. In both methods, the products were isolated in high yields and fully characterized using different spectral analysis techniques. The catalyst was reusable four times, and the activity was slightly decreased. The presence of Au increases the number of acidic sites of TiO 2 , resulting in C=O polarization. Yields of the prepared Schiff bases in the presence of Au@TiO 2 and piperidine were comparable. However, Au@TiO 2 is an easily separable and recyclable catalyst, which would facilitate the synthesis of organic compounds without applying any hazardous materials. Furthermore, the luminescence behavior of the synthesized Schiff bases exhibited spectral shape dependence on the substituent group. Interestingly, the compounds also displayed deep-blue fluorescence with Commission Internationale de l’Éclairage (CIE) coordinates of y < 0.1. Thus, these materials may contribute to decreasing the energy consumption of the emitting devices.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Base-Free Synthesis and Photophysical Properties of New Schiff Bases Containing Indole Moiety

et al. 2022

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“…amino-N-phenylglycinate (Sayed et al, 2018) A (0.3 g, 0.001 mol) of the compound (B) was dissolved in 15ml of ethanol with some drops of triethylamime. Then, (0.14 g, 0.001 mol) ethyl chloroacetate was added, stirring in a water bath at 67 o C for 2 hours and TLC monitored the progression.…”

Section: General Synthesis Proceduresmentioning

confidence: 99%

“…IR: 1670, 1063, 1562, 733, 2981, 3056 cm −1 , as shown in Scheme 9. (Sayed et al, 2018) The compound (I) (0.5 g, 0.001 mol) was dissolved in ethanol with some drops of triethylamine was added and stirred for 5 minutes. Then, (0.2 g, 0.001 mol) of ethyl chloroacetate was added slowly to the reaction solution, stirring in a water bath at 67 o C for more than 9 hours.…”

Section: General Synthesis Proceduresmentioning

confidence: 99%

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Synthesis and Characterization of Some Heterocyclic Compounds and Evaluation of Antibacterial Activity

Smaysem¹,

Salim²

2020

ijrps

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In this study, heterocyclic compounds with two nitrogen atoms are prepared by reaction of 2-aminobenzimidazole with formic acid to get amide derivatives (A), reacts with phenylhydrazine to get phenyl hydrazone derivatives (B), reacts with ethyl chloroacetate to obtain ethyl acetate derivatives (C). The derivative (D) obtains on heating in a basic medium. The (B) reacts with 2-chloroacetyl chloride to give derivatives (E). A number of Schiff bases are prepared (F, I) from reacting 2-aminobenzimidazole with benzaldehyde derivatives. The(F) reacts with propargyl bromide to give propargyl bromide derivatives (G). The cyclization with 4-nitrophenyl azide leads to obtain triazole compound (H). The compound (I) reacts with ethyl chloroacetate to give ethyl acetate derivatives (J), reacts with hydrazine to give N-amide hydrazine derivatives (K). The cyclization give rises to 1,3,4-oxadiazole derivatives (L). The compound (I) reacts with sodium azide to obtain tetrazole derivatives (M). Synthesizing of Triazine, Oxadiazole, Triazole, Tetrazole via cyclization of the Schiff base derivatives with ethyl chloroacetate and chloro acetyl chloride, benzoic acid, 4-nitrophenyl azide, sodium azide and phenyl azide are possible respectively. The FT-IR, 13C-NMR and 1H-NMR spectral data give good evidence for the formation of the compounds. Some prepared compounds exhibit antibacterial properties.

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F‐Tag Induced Acyl Shift in the Photochemical Cyclization of o‐Alkynylated N‐Alkyl‐N‐acylamides to Indoles**

et al. 2023

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A photochemical cyclization of F‐tagged, o‐alkynylated N‐alkylamides to indoles catalyzed by [Ir(dF(CF3)ppy)2(dtbpy)]PF6 is presented. This straightforward and efficient reaction involves an intramolecular rearrangement due to the presence of an electron withdrawing group in the acyl moiety and is the first example of photochemically induced 1,3‐acyl shift in the cyclization towards 3‐acylindoles. A four‐step reaction sequence including the photoreaction as a key step to the desired indoles has been developed and optimized. The compatibility of differently substituted F‐tagged precursors with the photocyclization step was investigated and the robustness of this step towards modifications could be shown. In total, 16 so far unknown derivatives with diverse modifications in positions N1 and C2, bearing a pentadecafluorooctanoyl moiety as F‐tag, were synthesized in very good yields and fully characterized.

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Synthesis of Some New Heterocyclic Compounds Containing Indole Moeity

Cited by 8 publications

References 7 publications

Base-Free Synthesis and Photophysical Properties of New Schiff Bases Containing Indole Moiety

Base-Free Synthesis and Photophysical Properties of New Schiff Bases Containing Indole Moiety

Synthesis and Characterization of Some Heterocyclic Compounds and Evaluation of Antibacterial Activity

F‐Tag Induced Acyl Shift in the Photochemical Cyclization of o‐Alkynylated N‐Alkyl‐N‐acylamides to Indoles**

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