One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles
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 / PyrazolesSource:
European Journal of Organic Chemistry, 2020, 2020, 34, 5616-5619Publisher:
- 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
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - 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 . .