One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles

Nikolić, Andrea; Živković, Filip; Selaković, Života; Wipf, Peter; Opsenica, Igor

doi:10.1002/ejoc.202000942

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2020

Authors

Nikolić, Andrea

Živković, Filip
Selaković, Života

Wipf, Peter
Opsenica, Igor

Article (Published version)

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Abstract

An efficient one-pot, two step method for fusing two biologically active motifs, CF3-substituted pyrazoles and isochromenes, was developed. Selective O-benzylation of CF3-substituted pyrazolones and subsequent Pd-catalyzed direct C–H arylation generate a fused tricycle. For the synthesized compounds through-space 13C–19F spin–spin coupling was revealed. In addition, the synthesis of three thioisochromene analogues, and one isocoumarin derivative, was accomplished.

Keywords:

C–F correlation / Heterocycles / Isochromenes / Palladium / Pyrazoles

Source:
European Journal of Organic Chemistry, 2020, 2020, 34, 5616-5619

Publisher:

Wiley

Funding / projects:

Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200168 (University of Belgrade, Faculty of Chemistry) (RS-200168)
SerbianAcademy of Sciences and Arts under strategic projects pro-gramme - grant agreement No. 01-2019-F65.
Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)

DOI: 10.1002/ejoc.202000942

ISSN: 1099-0690

WoS: 000558493900001

Scopus: 2-s2.0-85089311831

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	3
	1

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Živković, Filip
AU  - Selaković, Života
AU  - Wipf, Peter
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4294
AB  - An efficient one-pot, two step method for fusing two biologically active motifs, CF3-substituted pyrazoles and isochromenes, was developed. Selective O-benzylation of CF3-substituted pyrazolones and subsequent Pd-catalyzed direct C–H arylation generate a fused tricycle. For the synthesized compounds through-space 13C–19F spin–spin coupling was revealed. In addition, the synthesis of three thioisochromene analogues, and one isocoumarin derivative, was accomplished.
PB  - Wiley
T2  - European Journal of Organic Chemistry
T1  - One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles
VL  - 2020
IS  - 34
SP  - 5616
EP  - 5619
DO  - 10.1002/ejoc.202000942
ER  -

@article{
author = "Nikolić, Andrea and Živković, Filip and Selaković, Života and Wipf, Peter and Opsenica, Igor",
year = "2020",
abstract = "An efficient one-pot, two step method for fusing two biologically active motifs, CF3-substituted pyrazoles and isochromenes, was developed. Selective O-benzylation of CF3-substituted pyrazolones and subsequent Pd-catalyzed direct C–H arylation generate a fused tricycle. For the synthesized compounds through-space 13C–19F spin–spin coupling was revealed. In addition, the synthesis of three thioisochromene analogues, and one isocoumarin derivative, was accomplished.",
publisher = "Wiley",
journal = "European Journal of Organic Chemistry",
title = "One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles",
volume = "2020",
number = "34",
pages = "5616-5619",
doi = "10.1002/ejoc.202000942"
}

Nikolić, A., Živković, F., Selaković, Ž., Wipf, P.,& Opsenica, I.. (2020). One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles. in European Journal of Organic Chemistry
Wiley., 2020(34), 5616-5619.
https://doi.org/10.1002/ejoc.202000942

Nikolić A, Živković F, Selaković Ž, Wipf P, Opsenica I. One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles. in European Journal of Organic Chemistry. 2020;2020(34):5616-5619.
doi:10.1002/ejoc.202000942 .

Nikolić, Andrea, Živković, Filip, Selaković, Života, Wipf, Peter, Opsenica, Igor, "One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles" in European Journal of Organic Chemistry, 2020, no. 34 (2020):5616-5619,
https://doi.org/10.1002/ejoc.202000942 . .