Issue 47, 2019

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

Abstract

A green process to access pyrazolo-fused 4-azafluorenones (indeno[1,2-b]pyrazolo[4,3-e]pyridines, IPP) 4a–x 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 7a–d containing different acceptor (A) or donor (D) aryl groups at position 4 of its fused system. The structures of products obtained (4a–x and 7a–d) were determined based on NMR experiments, HRMS analysis, and X-ray diffraction studies for 7b. The photophysical and computational studies of 7a–d 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Jun 2019
Accepted
24 Aug 2019
First published
30 Aug 2019
This article is Open Access
Creative Commons BY license

RSC Adv., 2019,9, 27318-27323

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

J. Orrego-Hernández, C. Lizarazo, J. Cobo and J. Portilla, RSC Adv., 2019, 9, 27318 DOI: 10.1039/C9RA04682H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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