Pyrazolo-fused 4-azafluorenones as key reagents for the synthesis of fluorescent dicyanovinylidene-substituted derivatives

A green process to access pyrazolo-fused 4-azafluorenones (indeno[1,2- b ]pyrazolo[4,3- e ]pyridines, IPP) 4ax via the three-component reaction between indan-1,3-dione ( 1 ), benzaldehydes 2 and 5-amino-1-arylpyrazoles 3 is described. These compounds were successfully used as precursors of the novel...

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Bibliographic Details
Published in:RSC advances 2019-08, Vol.9 (47), p.27318-27323
Main Authors: Orrego-Hernndez, Jessica, Lizarazo, Carolina, Cobo, Justo, Portilla, Jaime
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical compounds
Chemistry
Crystallography
Cyanides
Derivatives
Diketones
Fluorescence
NMR
Nuclear magnetic resonance
Pyridines
Reagents
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Summary:A green process to access pyrazolo-fused 4-azafluorenones (indeno[1,2- b ]pyrazolo[4,3- e ]pyridines, IPP) 4ax via the three-component reaction between indan-1,3-dione ( 1 ), benzaldehydes 2 and 5-amino-1-arylpyrazoles 3 is described. These compounds were successfully used as precursors of the novel dicyanovinylidene derivatives 7ad containing different acceptor (A) or donor (D) aryl groups at position 4 of its fused system. The structures of products obtained ( 4ax and 7ad ) were determined based on NMR experiments, HRMS analysis, and X-ray diffraction studies for 7b . The photophysical and computational studies of 7ad showed that these products are modulable ICT fluorophores, even some preliminary tests revealed that these compounds could be used as fluorescent chemodosimeters for cyanide detection. A green method for the three-component synthesis of an indeno[1,2- b ]pyrazolo[4,3- e ]pyridines library under microwave irradiation and their use in the preparation of novel fluorescent dicyanovinylidene-substituted derivatives is provided.
ISSN:2046-2069
2046-2069
DOI:10.1039/c9ra04682h