Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation Strategies
Over the past two decades, the copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition (CuAAC), commonly known as click chemistry, and C–H bond activation have gained significant attention and have emerged as key synthetic methodologies. In our efforts to synthesize fused nitrogen-containing hete...
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MDPI AG
2025-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/12/2588 |
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| author | Antonia Iazzetti Dario Allevi Giancarlo Fabrizi Yuri Gazzilli Antonella Goggiamani Federico Marrone Francesco Stipa Karim Ullah Roberta Zoppoli |
| author_facet | Antonia Iazzetti Dario Allevi Giancarlo Fabrizi Yuri Gazzilli Antonella Goggiamani Federico Marrone Francesco Stipa Karim Ullah Roberta Zoppoli |
| author_sort | Antonia Iazzetti |
| collection | DOAJ |
| description | Over the past two decades, the copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition (CuAAC), commonly known as click chemistry, and C–H bond activation have gained significant attention and have emerged as key synthetic methodologies. In our efforts to synthesize fused nitrogen-containing heterocycles, we developed a palladium-catalyzed protocol for the synthesis of functionalized 7,10-dihydropyrrolo[3,2,1-ij][1,2,3]triazolo[4,5-c]quinolines and 5,8-dihydrobenzo[3,4][1,2,3]triazolo[4′,5′:5,6]azepino[1,2-a]indoles from suitable bromo-substituted <i>N</i>-propargyl-indoles. The reaction conditions demonstrate broad functional group compatibility including halogen, alkoxyl, cyano, ketone, and ester, affording the target compounds in good to high yields. |
| format | Article |
| id | doaj-art-39cb1ca5d2c04d8ca067e54e397a1a14 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-39cb1ca5d2c04d8ca067e54e397a1a142025-08-20T03:27:40ZengMDPI AGMolecules1420-30492025-06-013012258810.3390/molecules30122588Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation StrategiesAntonia Iazzetti0Dario Allevi1Giancarlo Fabrizi2Yuri Gazzilli3Antonella Goggiamani4Federico Marrone5Francesco Stipa6Karim Ullah7Roberta Zoppoli8Dipartimento di Scienze Biotecnologiche di Base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, ItalyDipartimento di Scienze Biotecnologiche di Base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, ItalyDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, ItalyOver the past two decades, the copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition (CuAAC), commonly known as click chemistry, and C–H bond activation have gained significant attention and have emerged as key synthetic methodologies. In our efforts to synthesize fused nitrogen-containing heterocycles, we developed a palladium-catalyzed protocol for the synthesis of functionalized 7,10-dihydropyrrolo[3,2,1-ij][1,2,3]triazolo[4,5-c]quinolines and 5,8-dihydrobenzo[3,4][1,2,3]triazolo[4′,5′:5,6]azepino[1,2-a]indoles from suitable bromo-substituted <i>N</i>-propargyl-indoles. The reaction conditions demonstrate broad functional group compatibility including halogen, alkoxyl, cyano, ketone, and ester, affording the target compounds in good to high yields.https://www.mdpi.com/1420-3049/30/12/2588palladium catalysis1,2,3-triazolestriazoloquinolinestriazoloazepinoindolesCuAACC–H bond activation |
| spellingShingle | Antonia Iazzetti Dario Allevi Giancarlo Fabrizi Yuri Gazzilli Antonella Goggiamani Federico Marrone Francesco Stipa Karim Ullah Roberta Zoppoli Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation Strategies Molecules palladium catalysis 1,2,3-triazoles triazoloquinolines triazoloazepinoindoles CuAAC C–H bond activation |
| title | Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation Strategies |
| title_full | Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation Strategies |
| title_fullStr | Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation Strategies |
| title_full_unstemmed | Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation Strategies |
| title_short | Construction of 1,2,3-Triazole-Embedded Polyheterocyclic Compounds via CuAAC and C–H Activation Strategies |
| title_sort | construction of 1 2 3 triazole embedded polyheterocyclic compounds via cuaac and c h activation strategies |
| topic | palladium catalysis 1,2,3-triazoles triazoloquinolines triazoloazepinoindoles CuAAC C–H bond activation |
| url | https://www.mdpi.com/1420-3049/30/12/2588 |
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