2026-10-29T13:13:08Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/60932022-11-11T12:52:48Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Velasco Pérez, Noelia
Suárez, Anisley
Martínez Lara, Fernando
Fernández Rodríguez, Manuel A.
Sanz Díez, Roberto
Suarez Pantiga, Samuel
2021-11-04T10:13:47Z
2021-11-04T10:13:47Z
2021-04
0022-3263
http://hdl.handle.net/10259/6093
10.1021/acs.joc.1c00333
1520-6904
This work describes the 6-endo-dig cyclization of Saryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing
intramolecular silver-catalyzed alkyne hydroarylation and Niodosuccinimide-promoted iodoarylation. Additionally, a PTSAcatalyzed thiolation reaction of propargylic alcohols was developed
to synthesize the required tertiary S-aryl propargyl ethers. The
applicability of merging these two methods is demonstrated by
synthesizing the retinoic acid receptor antagonist AGN194310.
Junta de Castilla y León
and FEDER (BU291P18 and BU049P20) and Ministerio de
Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P)
for financial support. The project leading to these results has
received funding from “la Caixa” Foundation, under Agreement
LCF/PR/PR18/51130007> (CAIXA-UBU001). N.V.,
F.M.-L., and S.S.-P. thank Junta de Castilla y León and FSE
and FEDER for predoctoral (N.V. and F.M.-L.) and
postdoctoral (S.S.-P.) contracts, respectively.
application/pdf
eng
American Chemical Society
The Journal of Organic Chemistry. 2021, V. 86, n. 10, 7078−7091
https://doi.org/10.1021/acs.joc.1c00333
info:eu-repo/grantAgreement/Junta de Castilla y León//BU291P18
info:eu-repo/grantAgreement/Junta de Castilla y León//BU049P20
info:eu-repo/grantAgreement/Fundación Bancaria Caixa d'Estalvis i Pensions de Barcelona//LCF%2FPR%2FPR18%2F51130007 (CAIXA-UBU001)
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75023-C2-1-P/ES/DESARROLLO DE NUEVAS METODOLOGIAS SINTETICAS. APLICACION A LA PREPARACION DE MOLECULAS DE INTERES Y A LA VALORIZACION DE LA LIGNINA
Atribución 4.0 Internacional
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
Sulfides
Alcohols
Column chromatography
Cyclization
Propargyls
Química orgánica
Chemistry, Organic
From Propargylic Alcohols to Substituted Thiochromenes: gem- Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion