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

Polo, Efrain; Arce-Parada, Valentina; Lopez-Cortes, Xaviera A.; Sanchez-Marquez, Jesus; Morales-Bayuelo, Alejandro; Forero-Doria, Oscar; Gutierrez, Margarita

Abstract

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.

Más información

Título según WOS: Synthesis of Pyrazolo-Fused 4-Azafluorenones in an Ionic Liquid. Mechanistic Insights by Joint Studies Using DFT Analysis and Mass Spectrometry
Título según SCOPUS: Synthesis of pyrazolo-fused 4-azafluorenones in an ionic liquid. mechanistic insights by joint studies using DFT analysis and mass spectrometry
Título de la Revista: CATALYSTS
Volumen: 9
Número: 10
Editorial: MDPI
Fecha de publicación: 2019
Idioma: English
DOI:

10.3390/catal9100820

Notas: ISI, SCOPUS