Straightforward Synthesis of Bis[(trifluoromethyl)sulfonyl]ethylated Isocoumarins from 2-Ethynylbenzoates

Petcu, Sonia; Lázaro Milla, Carlos; Rodríguez,  Javier; Iriepa, Isabel; Bautista-Aguilera, Óscar; Aragoncillo Abanades, Cristina; Alonso Gómez, José Miguel; Almendros Requena, Pedro

Straightforward Synthesis of Bis[(trifluoromethyl)sulfonyl]ethylated Isocoumarins from 2-Ethynylbenzoates

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Official URL

https://doi.org/10.1021/acs.joc.3c00611

Publication date

2023

Authors

Petcu, Sonia

Lázaro Milla, Carlos

Rodríguez, Javier

Iriepa, Isabel

Bautista-Aguilera, Óscar

Aragoncillo Abanades, Cristina

Alonso Gómez, José Miguel

Almendros Requena, Pedro

Publisher

American Chemical Society

Citations

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URI

https://hdl.handle.net/20.500.14352/91922

Citation

Petcu A S, Lázaro-Milla C, Rodríguez F J, Iriepa I, Bautista-Aguilera, Ó M, Aragoncillo C, Alonso J M, Almendros P. Straightforward Synthesis of Bis[(trifluoromethyl)sulfonyl]ethylated Isocoumarins from 2-Ethynylbenzoates. J. Org. Chem. 2023 , 88, 7373-7380.

Abstract

Herein, we report a facile isocoumarin and isoquinolone preparation by taking advantage of an initial bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] reaction, followed by heterocyclization, which contrasts with our previous results on cyclobutene formation. The efficiency of the catalyst- and irradiation-free heterocyclization/bis(triflyl)ethylation sequence showed exquisite dependence on the electronic nature of the substituents at the 2-ethynylbenzoate(benzamide) precursors. Molecular docking of model bis(triflyl)ethylated isocoumarins on human acetylcholinesterase (hAChE) revealed promising biological activities through selective coordination on both the catalytic active site and peripheral active site.