Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3H-Indoles

In this study, novel fluorescent 5-aryl-2-styryl-3<i>H</i>-indole derivatives were efficiently synthesized from 4-bromophenylhydrazine hydrochloride using the microwave-accelerated one-pot technique, which includes Fischer synthesis, Suzuki cross-coupling, and Knoevenagel condensation. The structural assignments of the synthesized compounds were based on <sup>1</sup>H, <sup>13</sup>C, <sup>15</sup>N, and <sup>19</sup>F NMR; IR spectroscopy; and HRMS spectral data. The optical properties of the newly obtained styryl-indole dyes were studied using UV-vis and fluorescence spectroscopy, which clearly demonstrated that the derivatives substituted with electron-donating or -withdrawing groups exhibited varying emission shifts and quantum yields ranging from negligible to high.

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Publication Details

Journal
Molecules
Published
2025-06-07
DOI
https://doi.org/10.3390/molecules30122503
Primary Topic
Synthesis of Organic Compounds
Type
article
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article

Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3H-Indoles

Neringa Kleizienė, Algirdas Šačkus, Aurimas Bieliauskas, Martynas R. Bartkus
Molecules
Synthesis of Organic Compounds
article

Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3H-Indoles

Neringa Kleizienė, Algirdas Šačkus, Aurimas Bieliauskas, Martynas R. Bartkus
article en

Abstract

In this study, novel fluorescent 5-aryl-2-styryl-3<i>H</i>-indole derivatives were efficiently synthesized from 4-bromophenylhydrazine hydrochloride using the microwave-accelerated one-pot technique, which includes Fischer synthesis, Suzuki cross-coupling, and Knoevenagel condensation. The structural assignments of the synthesized compounds were based on <sup>1</sup>H, <sup>13</sup>C, <sup>15</sup>N, and <sup>19</sup>F NMR; IR spectroscopy; and HRMS spectral data. The optical properties of the newly obtained styryl-indole dyes were studied using UV-vis and fluorescence spectroscopy, which clearly demonstrated that the derivatives substituted with electron-donating or -withdrawing groups exhibited varying emission shifts and quantum yields ranging from negligible to high.

MoleculesVol. 30(12)
Kaunas University of Technology (LT)
Openalex Percentile: Top 85%
Synthesis of Organic Compounds
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