Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-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. T...
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MDPI AG
2025-06-01
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| Series: | Molecules |
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| author | Martynas Rojus Bartkus Neringa Kleizienė Aurimas Bieliauskas Algirdas Šačkus |
| author_facet | Martynas Rojus Bartkus Neringa Kleizienė Aurimas Bieliauskas Algirdas Šačkus |
| author_sort | Martynas Rojus Bartkus |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-4927e14cbb0b4c63b4da7b0b4090a4dd |
| institution | Matheson Library |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-4927e14cbb0b4c63b4da7b0b4090a4dd2025-06-25T14:13:23ZengMDPI AGMolecules1420-30492025-06-013012250310.3390/molecules30122503Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-IndolesMartynas Rojus Bartkus0Neringa Kleizienė1Aurimas Bieliauskas2Algirdas Šačkus3Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, LithuaniaInstitute of Synthetic Chemistry, Kaunas University of Technology, K. Baršausko g. 59, LT-51423 Kaunas, LithuaniaInstitute of Synthetic Chemistry, Kaunas University of Technology, K. Baršausko g. 59, LT-51423 Kaunas, LithuaniaDepartment of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, LithuaniaIn 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.https://www.mdpi.com/1420-3049/30/12/2503one-pot synthesisconsecutive multicomponent reactionmicrowave synthesisFischer synthesisSuzuki cross-coupling reactionKnoevenagel condensation |
| spellingShingle | Martynas Rojus Bartkus Neringa Kleizienė Aurimas Bieliauskas Algirdas Šačkus Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-Indoles Molecules one-pot synthesis consecutive multicomponent reaction microwave synthesis Fischer synthesis Suzuki cross-coupling reaction Knoevenagel condensation |
| title | Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-Indoles |
| title_full | Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-Indoles |
| title_fullStr | Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-Indoles |
| title_full_unstemmed | Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-Indoles |
| title_short | Facile One-Pot Fischer–Suzuki–Knoevenagel Microwave-Assisted Synthesis of Fluorescent 5-Aryl-2-Styryl-3<i>H</i>-Indoles |
| title_sort | facile one pot fischer suzuki knoevenagel microwave assisted synthesis of fluorescent 5 aryl 2 styryl 3 i h i indoles |
| topic | one-pot synthesis consecutive multicomponent reaction microwave synthesis Fischer synthesis Suzuki cross-coupling reaction Knoevenagel condensation |
| url | https://www.mdpi.com/1420-3049/30/12/2503 |
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