From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation

[Image: see text] This work describes the 6-endo-dig cyclization of S-aryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and N-iodosuccinimide-promoted iodoarylation....

Descripción completa

Detalles Bibliográficos
Autores principales: Velasco, Noelia, Suárez, Anisley, Martínez-Lara, Fernando, Fernández-Rodríguez, Manuel Ángel, Sanz, Roberto, Suárez-Pantiga, Samuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8474117/
https://www.ncbi.nlm.nih.gov/pubmed/33928778
http://dx.doi.org/10.1021/acs.joc.1c00333
_version_ 1784575149526220800
author Velasco, Noelia
Suárez, Anisley
Martínez-Lara, Fernando
Fernández-Rodríguez, Manuel Ángel
Sanz, Roberto
Suárez-Pantiga, Samuel
author_facet Velasco, Noelia
Suárez, Anisley
Martínez-Lara, Fernando
Fernández-Rodríguez, Manuel Ángel
Sanz, Roberto
Suárez-Pantiga, Samuel
author_sort Velasco, Noelia
collection PubMed
description [Image: see text] This work describes the 6-endo-dig cyclization of S-aryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and N-iodosuccinimide-promoted iodoarylation. Additionally, a PTSA-catalyzed 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.
format Online
Article
Text
id pubmed-8474117
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-84741172021-09-28 From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation Velasco, Noelia Suárez, Anisley Martínez-Lara, Fernando Fernández-Rodríguez, Manuel Ángel Sanz, Roberto Suárez-Pantiga, Samuel J Org Chem [Image: see text] This work describes the 6-endo-dig cyclization of S-aryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and N-iodosuccinimide-promoted iodoarylation. Additionally, a PTSA-catalyzed 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. American Chemical Society 2021-04-30 2021-05-21 /pmc/articles/PMC8474117/ /pubmed/33928778 http://dx.doi.org/10.1021/acs.joc.1c00333 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Velasco, Noelia
Suárez, Anisley
Martínez-Lara, Fernando
Fernández-Rodríguez, Manuel Ángel
Sanz, Roberto
Suárez-Pantiga, Samuel
From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
title From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
title_full From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
title_fullStr From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
title_full_unstemmed From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
title_short From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation
title_sort from propargylic alcohols to substituted thiochromenes: gem-disubstituent effect in intramolecular alkyne iodo/hydroarylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8474117/
https://www.ncbi.nlm.nih.gov/pubmed/33928778
http://dx.doi.org/10.1021/acs.joc.1c00333
work_keys_str_mv AT velasconoelia frompropargylicalcoholstosubstitutedthiochromenesgemdisubstituenteffectinintramolecularalkyneiodohydroarylation
AT suarezanisley frompropargylicalcoholstosubstitutedthiochromenesgemdisubstituenteffectinintramolecularalkyneiodohydroarylation
AT martinezlarafernando frompropargylicalcoholstosubstitutedthiochromenesgemdisubstituenteffectinintramolecularalkyneiodohydroarylation
AT fernandezrodriguezmanuelangel frompropargylicalcoholstosubstitutedthiochromenesgemdisubstituenteffectinintramolecularalkyneiodohydroarylation
AT sanzroberto frompropargylicalcoholstosubstitutedthiochromenesgemdisubstituenteffectinintramolecularalkyneiodohydroarylation
AT suarezpantigasamuel frompropargylicalcoholstosubstitutedthiochromenesgemdisubstituenteffectinintramolecularalkyneiodohydroarylation

Ejemplares similares