Palladium iodide-catalyzed selective carbonylative double cyclization of 4-(2-aminophenyl)-3-yn-1-ols to dihydrofuroquinolinone derivatives

Article

Mancuso, R., De Salvo, A., Russo, P., Falcicchio, A., Ca’, N.D., Pantoja Munoz, L. and Gabriele, B. 2023. Palladium iodide-catalyzed selective carbonylative double cyclization of 4-(2-aminophenyl)-3-yn-1-ols to dihydrofuroquinolinone derivatives. Chinese Journal of Chemistry. 41 (21), pp. 2801-2809. https://doi.org/10.1002/cjoc.202300277
TypeArticle
TitlePalladium iodide-catalyzed selective carbonylative double cyclization of 4-(2-aminophenyl)-3-yn-1-ols to dihydrofuroquinolinone derivatives
AuthorsMancuso, R., De Salvo, A., Russo, P., Falcicchio, A., Ca’, N.D., Pantoja Munoz, L. and Gabriele, B.
Abstract

The PdI2/KI‐catalyzed oxidative carbonylation of 4‐(2‐aminophenyl)‐3‐yn‐1‐ols, bearing two potential nucleophilic groups in suitable position selectively leads to dihydrofuroquinolinone derivatives in fair to high yields (60%—89%) and excellent turnover numbers (180—267 mol of product per mol of Pd) over 19 examples, through a mechanistic pathway involving initial O‐cyclization followed by N‐cyclocarbonylation. In such process, the selective catalytic construction of two rings and three new bonds is achieved in one synthetic step to afford high value added fused heterocyclic structures starting from readily available materials.

KeywordsCarbonylation; Cyclization; Heterocycles; Palladium; Polycyclic heterocycles
Sustainable Development Goals12 Responsible consumption and production
Middlesex University ThemeCreativity, Culture & Enterprise
PublisherWiley
JournalChinese Journal of Chemistry
ISSN1001-604X
Electronic1614-7065
Publication dates
Online26 Jul 2023
Print01 Nov 2023
Publication process dates
Submitted04 May 2023
Accepted26 Jun 2023
Deposited16 Oct 2024
Output statusPublished
Publisher's version
License
File Access Level
Open
Copyright Statement

© 2023 The Authors. Chinese Journal of Chemistry published by SIOC, CAS, Shanghai and Wiley-VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.

Digital Object Identifier (DOI)https://doi.org/10.1002/cjoc.202300277
Permalink -

https://repository.mdx.ac.uk/item/1qq31v

Log in to edit

Download files

Publisher's version
Chinese Journal of Chemistry - 2023 - Mancuso - Palladium Iodide‐Catalyzed Selective Carbonylative Double Cyclization of 4‐.pdf
License: CC BY-NC-ND 4.0
File access level: Open

  • 7
    total views
  • 1
    total downloads
  • 4
    views this month
  • 0
    downloads this month

Export as

Related outputs

A study of bacteria producing carbonic anhydrase enzyme for CaCO3 precipitation and soil biocementation
Meandira, W., Mavroulidou, M., Timmermans, M., Gunn, M., Gray, C., Pantoja Munoz, L. and Purchase, D. 2024. A study of bacteria producing carbonic anhydrase enzyme for CaCO3 precipitation and soil biocementation. Environmental Science and Pollution Research. 31 (33), pp. 45818-45833. https://doi.org/10.1007/s11356-024-34077-0
Molding the future: optimization of bioleaching of rare earth elements from electronic waste by Penicillium expansum and insights into its mechanism
Gonzalez Baez, A., Pantoja Munoz, L., Timmermans, M., Garelick, H. and Purchase, D. 2024. Molding the future: optimization of bioleaching of rare earth elements from electronic waste by Penicillium expansum and insights into its mechanism. Bioresource Technology. 402. https://doi.org/10.1016/j.biortech.2024.130750
An assessment of different alkali-activated cements as stabilizers of sulfate-bearing soils
Mavroulidou, M., Gray, C., Pantoja Munoz, L. and Gunn, M. 2023. An assessment of different alkali-activated cements as stabilizers of sulfate-bearing soils. Quarterly Journal of Engineering Geology and Hydrogeology. 56 (2). https://doi.org/10.1144/qjegh2022-057
Absence of Staphylococcus aureus in wild populations of fish supports a spillover hypothesis
Matuszewska, M., Dabrowska, A., Murray, G., Kett, S., Vick, A., Banister, S., Pantoja Munoz, L., Cunningham, P., Welch, J., Holmes, M. and Weinert, L. 2023. Absence of Staphylococcus aureus in wild populations of fish supports a spillover hypothesis. Microbiology Spectrum. 11 (4). https://doi.org/10.1128/spectrum.04858-22
A critical review of the quantification, analysis and detection of radionuclides in the environment using diffusive gradients in thin films (DGT): advances and perspectives
Pantoja Munoz, L. and Garelick, H. 2023. A critical review of the quantification, analysis and detection of radionuclides in the environment using diffusive gradients in thin films (DGT): advances and perspectives. Pure and Applied Chemistry. 96 (7), pp. 923-937. https://doi.org/10.1515/pac-2023-0809
Characterization of industrially pre-treated waste printed circuit boards for the potential recovery of rare earth elements
Gonzalez Baez, A., Pantoja Munoz, L., Garelick, H. and Purchase, D. 2022. Characterization of industrially pre-treated waste printed circuit boards for the potential recovery of rare earth elements. Environmental Technology and Innovation. 27. https://doi.org/10.1016/j.eti.2022.102481
Release of microplastic fibres and fragmentation to billions of nanoplastics from period products: preliminary assessment of potential health implications
Pantoja Munoz, L., Gonzalez Baez, A., Purchase, D., Jones, H. and Garelick, H. 2022. Release of microplastic fibres and fragmentation to billions of nanoplastics from period products: preliminary assessment of potential health implications. Environmental Science: Nano. 9 (2), pp. 606-620. https://doi.org/10.1039/d1en00755f
Natural based products for cleaning copper and copper alloys artefacts
Macchia, A., Colasanti, I., Rivaroli, L., Favero, G., de Caro, T., Pantoja Munoz, L., Campanella, L. and La Russa, M. 2023. Natural based products for cleaning copper and copper alloys artefacts. Natural Product Research. 37 (7), pp. 1177-1184. https://doi.org/10.1080/14786419.2021.2000408
Waste printed circuit boards (WPCBs) as a potential source for the recovery of rare earth elements through bioleaching
Gonzalez Baez, A., Pantoja Munoz, L., Garelick, H. and Purchase, D. 2021. Waste printed circuit boards (WPCBs) as a potential source for the recovery of rare earth elements through bioleaching. 17th International Conference on Environmental Science and Technology CEST2021. Athens, Greece 01 - 04 Sep 2021
A bioleaching approach for the recovery of rare earth elements (REE) from waste printed circuit boards (WPCBs)
Gonzalez Baez, A., Pantoja Munoz, L., Garelick, H. and Purchase, D. 2021. A bioleaching approach for the recovery of rare earth elements (REE) from waste printed circuit boards (WPCBs). IUPAC 48th World Chemistry Congress. Montreal, Canada 13 - 20 Aug 2021
Exploiting the efficacy of Tyro3 and folate receptors to enhance the delivery of gold nanoparticles into colorectal cancer cells in vitro
Patel, N., Ghali, L., Roitt, I., Pantoja Munoz, L. and Bayford, R. 2021. Exploiting the efficacy of Tyro3 and folate receptors to enhance the delivery of gold nanoparticles into colorectal cancer cells in vitro. Nanoscale Advances. 3 (18), pp. 5373-5386. https://doi.org/10.1039/d1na00318f
Recovery of rare earth elements from electronic waste through bioleaching
Gonzalez Baez, A., Pantoja Munoz, L., Garelick, H. and Purchase, D. 2020. Recovery of rare earth elements from electronic waste through bioleaching. LSBU 100 Women in Engineering - Engineering a World That Works For Everyone. London, UK 17 Nov 2020
A global multinational survey of cefotaxime-resistant coliforms in urban wastewater treatment plants
Marano, R., Fernandes, T., Manaia, C., Nunes, O., Morrison, D., Berendonk, T., Kreuzinger, N., Telson, T., Corno, G., Fatta-Kassinos, D., Merlin, C., Topp, E., Jurkevitch, E., Henn, L., Scott, A., Heß, S., Slipko, K., Laht, M., Kisand, V., Di Cesare, A., Karaolia, P., Michael, S., Petre, A., Rosal, R., Pruden, A., Riquelme, V., Agüera, A., Esteban, B., Luczkiewicz, A., Kalinowska, A., Leonard, A., Gaze, W., Adegoke, A., Stenstrom, T., Pollice, A., Salerno, C., Schwermer, C., Krzeminski, P., Guilloteau, H., Donner, E., Drigo, B., Libralato, G., Guida, M., Bürgmann, H., Beck, K., Garelick, H., Tacão, M., Henriques, I., Martínez-Alcalá, I., Guillén-Navarro, J., Popowska, M., Piotrowska, M., Quintela-Baluja, M., Bunce, J., Polo-López, M., Nahim-Granados, S., Pons, M., Milakovic, M., Udikovic-Kolic, N., Ory, J., Ousmane, T., Caballero, P., Oliver, A., Rodriguez-Mozaz, S., Balcazar, J., Jäger, T., Schwartz, T., Yang, Y., Zou, S., Lee, Y., Yoon, Y., Herzog, B., Mayrhofer, H., Prakash, O., Nimonkar, Y., Heath, E., Baraniak, A., Abreu-Silva, J., Choudhury, M., Pantoja Munoz, L., Krizanovic, S., Brunetti, G., Maile-Moskowitz, A., Brown, C. and Cytryn, E. 2020. A global multinational survey of cefotaxime-resistant coliforms in urban wastewater treatment plants. Environment International. 144, pp. 1-11. https://doi.org/10.1016/j.envint.2020.106035
Antibiotic selective pressure in microcosms: pollution influences the persistence of multidrug resistant Shigella flexneri 2a YSH6000 strain in polluted river water samples
Maruzani, R., Pathak, A., Ward, M., Serafim, V., Pantoja Munoz, L., Shah, A. and Marvasi, M. 2020. Antibiotic selective pressure in microcosms: pollution influences the persistence of multidrug resistant Shigella flexneri 2a YSH6000 strain in polluted river water samples. Environmental Technology and Innovation. 19. https://doi.org/10.1016/j.eti.2020.100821
Characterisation of rare earth elements in waste printed circuit boards (WPCBs) and their bioleaching potential
Gonzalez Baez, A., Pantoja Munoz, L., Garelick, H. and Purchase, D. 2019. Characterisation of rare earth elements in waste printed circuit boards (WPCBs) and their bioleaching potential. 16th International Conference on Environmental Science and Technology. Rhodes, Greece 04 - 07 Sep 2019
Characterisation of "flushable" and "non-flushable" commercial wet wipes using microRaman, FTIR spectroscopy and fluorescence microscopy: to flush or not to flush
Pantoja Munoz, L., Gonzalez Baez, A., McKinney, D. and Garelick, H. 2018. Characterisation of "flushable" and "non-flushable" commercial wet wipes using microRaman, FTIR spectroscopy and fluorescence microscopy: to flush or not to flush. Environmental Science and Pollution Research. 25 (20), pp. 20268-20279. https://doi.org/10.1007/s11356-018-2400-9
Effect of anthropogenic pollution on the fitness of tetracycline sensitive Shigella flexneri in Thames river water
Maruzani, R., Canali, A., Serafim, V., Pantoja Munoz, L., Shah, A., Perito, B. and Marvasi, M. 2018. Effect of anthropogenic pollution on the fitness of tetracycline sensitive Shigella flexneri in Thames river water. Journal of Environmental Chemical Engineering. 6 (1), pp. 19-27. https://doi.org/10.1016/j.jece.2017.11.069
Fitness analysis of tetracycline resistant and sensitive Shigella flexneri in lethal and sub-lethal concentrations of tetracycline in Thames river water microcosms
Maruzani, R., Shah, A., Pantoja Munoz, L. and Marvasi, M. 2017. Fitness analysis of tetracycline resistant and sensitive Shigella flexneri in lethal and sub-lethal concentrations of tetracycline in Thames river water microcosms. University Research Students Summer Conference 2017. London 2017
Microbial DNA analysis by MALDI-TOF mass spectrometry
Honisch, C., Serafim, V., Hennessy, N., Allen, D., Ring, C., Pantoja Munoz, L., Gharbia, S., Shah, A. and Shah, H. 2017. Microbial DNA analysis by MALDI-TOF mass spectrometry. in: Shah, H. and Gharbia, S. (ed.) MALDI-TOF and Tandem MS for Clinical Microbiology Oxford Wiley. pp. 187-209
A study of the inhibition of biofilm formation on multiple surfaces by a biosurfactant containing four discrete lipopeptides
Khonsari, S., Gonzalez Baez, A., Nguyen, H., Pantoja Munoz, L. and Purchase, D. 2017. A study of the inhibition of biofilm formation on multiple surfaces by a biosurfactant containing four discrete lipopeptides. Microbiology Society Annual Conference. Edinburgh, United Kingdom 03 - 06 Apr 2017
Rapid identification of E. coli bacteriophages using mass spectrometry
Serafim, V., Ring, C., Pantoja Munoz, L., Shah, H. and Shah, A. 2017. Rapid identification of E. coli bacteriophages using mass spectrometry. Journal of Proteomics and Enzymology. 6 (1), pp. 1-5. https://doi.org/10.4172/2470-1289.1000130
Heparan sulfate disaccharide measurement from biological samples using pre-column derivatization, UPLC-MS and single ion monitoring
Antia, I., Yagnik, D., Pantoja Munoz, L., Shah, A. and Hills, F. 2017. Heparan sulfate disaccharide measurement from biological samples using pre-column derivatization, UPLC-MS and single ion monitoring. Analytical Biochemistry. 530, pp. 17-30. https://doi.org/10.1016/j.ab.2017.04.019
The mechanisms of detoxification of As(III), dimethylarsinic acid (DMA) and As(V) in the microalga Chlorella vulgaris
Pantoja Munoz, L., Purchase, D., Jones, H., Raab, A., Urgast, D., Feldmann, J. and Garelick, H. 2016. The mechanisms of detoxification of As(III), dimethylarsinic acid (DMA) and As(V) in the microalga Chlorella vulgaris. Aquatic Toxicology. 175, pp. 56-72. https://doi.org/10.1016/j.aquatox.2016.02.020
Therapeutic potential of delivering arsenic trioxide into HPV-infected cervical cancer cells using liposomal nanotechnology
Wang, X., Li, D., Ghali, L., Xia, R., Pantoja Munoz, L., Garelick, H., Bell, C. and Wen, S. 2016. Therapeutic potential of delivering arsenic trioxide into HPV-infected cervical cancer cells using liposomal nanotechnology. Nanoscale Research Letters. 11 (1), pp. 1-8. https://doi.org/10.1186/s11671-016-1307-y
Consideration of the bioavailability of metal/metalloid species in freshwaters: experiences regarding the implementation of biotic ligand model-based approaches in risk assessment frameworks
Rüdel, H., Diaz Muñiz, C., Garelick, H., Kandile, N., Miller, B., Pantoja Munoz, L., Peijnenburg, W., Purchase, D., Shevah, Y., Van Sprang, P., Vijer, M. and Vink, J. 2015. Consideration of the bioavailability of metal/metalloid species in freshwaters: experiences regarding the implementation of biotic ligand model-based approaches in risk assessment frameworks. Environmental Science and Pollution Research. 22 (10), pp. 7405-7421. https://doi.org/10.1007/s11356-015-4257-5
The mechanisms of arsenic detoxification by the green microalgae chlorella vulgaris
Pantoja Munoz, L. 2014. The mechanisms of arsenic detoxification by the green microalgae chlorella vulgaris. PhD thesis Middlesex University Science and Technology
The mechanisms of arsenic bioremediation from water by the green microalgae Chlorella vulgaris
Pantoja Munoz, L., Purchase, D., Jones, H., Feldmann, J. and Garelick, H. 2014. The mechanisms of arsenic bioremediation from water by the green microalgae Chlorella vulgaris. THE BNASS / TraceSpec Tandem Conference. Aberdeen, Scotland, UK 31 Aug - 04 Sep 2014
Enhanced determination of As-phytochelatin complexes in Chlorella vulgaris using focused sonication for extraction of water-soluble species
Pantoja Munoz, L., Purchase, D., Jones, H., Feldmann, J. and Garelick, H. 2014. Enhanced determination of As-phytochelatin complexes in Chlorella vulgaris using focused sonication for extraction of water-soluble species. Analytical Methods. 6 (3), pp. 791-797. https://doi.org/10.1039/C3AY41629A
The removal of arsenate from water using iron-modified diatomite (D-Fe): isotherm and column experiments
Pantoja Munoz, L., Jones, H., Garelick, H., Mohamedbakr, H. and Burkitbayev, M. 2014. The removal of arsenate from water using iron-modified diatomite (D-Fe): isotherm and column experiments. Environmental Science and Pollution Research. 21 (1), pp. 495-506. https://doi.org/10.1007/s11356-013-1891-7