Next Article in Journal
Surface Modification of Nanocrystalline TiO2 Materials with Sulfonated Porphyrins for Visible Light Antimicrobial Therapy
Next Article in Special Issue
Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles
Previous Article in Journal
Enhanced Visible Light Photodegradation of Microplastic Fragments with Plasmonic Platinum/Zinc Oxide Nanorod Photocatalysts
Open AccessArticle

Synthesis of Pyrazolo-Fused 4-Azafluorenones in an Ionic Liquid. Mechanistic Insights by Joint Studies Using DFT Analysis and Mass Spectrometry

1
Doctorado en Ciencias Mención I+D de Productos Bioactivos, Instituto de Química de Recursos Naturales, Laboratorio de Síntesis Orgánica, Universidad de Talca, Casilla 747, Talca 3460000, Chile
2
Facultad de Ciencias de la Salud, Escuela de Tecnología Médica, Universidad de Talca, Casilla 747, Talca 3460000, Chile
3
Department of Computer Science and Industries, Universidad Católica Del Maule, Maule 3340000, Chile
4
Departamento de Química-Física, Facultad de Ciencias, Campus Universitario Río San Pedro, Universidad de Cádiz, 11510 Puerto Real, Cádiz, Spain
5
Ciencias de la Salud, Grupo de Investigaciones Básicas y Clínicas de la Universidad del Sinú (GIBACUS), escuela de medicina, Universidad del Sinú, 130001 Montería, Córdoba, Colombia
6
Instituto de Química de Recursos Naturales, Laboratorio de Síntesis Orgánica, Universidad de Talca, Casilla 747, Talca 3460000, Chile
*
Authors to whom correspondence should be addressed.
Catalysts 2019, 9(10), 820; https://doi.org/10.3390/catal9100820
Received: 12 September 2019 / Revised: 25 September 2019 / Accepted: 27 September 2019 / Published: 29 September 2019
(This article belongs to the Special Issue Heterocyclic Chemistry and Catalysis)
A series of pyrazolo-fused 4-azafluorenones (indeno[1,2-b]pyrazolo[4,3-e]pyridines, IPP) were synthesized via the three-component reaction between arylaldehydes, 3-methyl-1H-pyrazol-5-amine and 1,3-indanedione in an ionic liquid as a catalyst at room temperature. The applied synthetic route has the advantages of easy work-up under mild reaction conditions presenting moderate yields and an environmentally benign procedure. A theoretical study based on conceptual-density functional theory has been done, bond reactivity indices have been calculated and an electrophilic and nucleophilic character of localized orbitals has been determined to analyze the possible electronic mechanisms. View Full-Text
Keywords: ionic liquid; condensation; 4-azafluorenones; ultrasound; reaction mechanism; mass spectrometry; DFT studies ionic liquid; condensation; 4-azafluorenones; ultrasound; reaction mechanism; mass spectrometry; DFT studies
Show Figures

Figure 1

MDPI and ACS Style

Polo, E.; Arce-Parada, V.; López-Cortés, X.A.; Sánchez-Márquez, J.; Morales-Bayuelo, A.; Forero-Doria, O.; Gutiérrez, M. Synthesis of Pyrazolo-Fused 4-Azafluorenones in an Ionic Liquid. Mechanistic Insights by Joint Studies Using DFT Analysis and Mass Spectrometry. Catalysts 2019, 9, 820.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop