RT info:eu-repo/semantics/article
T1 From Propargylic Alcohols to Substituted Thiochromenes: gem- Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
A1 Velasco Pérez, Noelia
A1 Suárez, Anisley
A1 Martínez Lara, Fernando
A1 Fernández Rodríguez, Manuel A.
A1 Sanz Díez, Roberto
A1 Suarez Pantiga, Samuel
K1 Sulfides
K1 Alcohols
K1 Column chromatography
K1 Cyclization
K1 Propargyls
K1 Química orgánica
K1 Chemistry, Organic
AB 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 allowingintramolecular silver-catalyzed alkyne hydroarylation and Niodosuccinimide-promoted iodoarylation. Additionally, a PTSAcatalyzed thiolation reaction of propargylic alcohols was developedto synthesize the required tertiary S-aryl propargyl ethers. Theapplicability of merging these two methods is demonstrated bysynthesizing the retinoic acid receptor antagonist AGN194310.
PB American Chemical Society
SN 0022-3263
YR 2021
FD 2021-04
LK http://hdl.handle.net/10259/6093
UL http://hdl.handle.net/10259/6093
LA eng
NO Junta de Castilla y Leónand FEDER (BU291P18 and BU049P20) and Ministerio deCiencia e Innovación and FEDER (CTQ2016-75023-C2-1-P)for financial support. The project leading to these results hasreceived funding from “la Caixa” Foundation, under AgreementLCF/PR/PR18/51130007> (CAIXA-UBU001). N.V.,F.M.-L., and S.S.-P. thank Junta de Castilla y León and FSEand FEDER for predoctoral (N.V. and F.M.-L.) andpostdoctoral (S.S.-P.) contracts, respectively.
DS Repositorio Institucional de la Universidad de Burgos
RD 04-may-2024