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 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.
Authors
- Federico Marrone (ORCID: https://orcid.org/0000-0003-2350-639X)
- Francesco Stipa (ORCID: https://orcid.org/0000-0002-8387-0452)
- Antonella Goggiamani (ORCID: https://orcid.org/0000-0001-8339-4284)
- Antonia Iazzetti (ORCID: https://orcid.org/0000-0002-7792-774X)
- Dario Allevi (ORCID: https://orcid.org/0000-0002-0188-9505)
- Roberta Zoppoli
- Giancarlo Fabrizi (ORCID: https://orcid.org/0000-0002-2717-9341)
- Karim Ullah (ORCID: https://orcid.org/0000-0003-0360-8903)
- Yuri Gazzilli
Institutions
- Università Cattolica del Sacro Cuore (IT)
- Agostino Gemelli University Polyclinic (IT)
- Istituti di Ricovero e Cura a Carattere Scientifico (IT)
- Sapienza University of Rome (IT)
Publication Details
- Journal
- Molecules
- Published
- 2025-06-13
- DOI
- https://doi.org/10.3390/molecules30122588
- Citations
- 1
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- European Commission
- Sapienza Università di Roma
- Università Cattolica del Sacro Cuore