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从丙炔醇到取代噻吩并[2,3-b]吡啶：分子内炔烃碘/氢芳基化中的-二取代基效应。

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

机构信息

Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, Spain.

Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Universidad de Alcalá (IRYCIS), 28805 Alcalá de Henares, Madrid, Spain.

出版信息

J Org Chem. 2021 May 21;86(10):7078-7091. doi: 10.1021/acs.joc.1c00333. Epub 2021 Apr 30.

DOI:10.1021/acs.joc.1c00333
PMID:33928778
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8474117/
Abstract

This work describes the 6-- cyclization of -aryl propargyl sulfides to afford 2-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and -iodosuccinimide-promoted iodoarylation. Additionally, a PTSA-catalyzed thiolation reaction of propargylic alcohols was developed to synthesize the required tertiary -aryl propargyl ethers. The applicability of merging these two methods is demonstrated by synthesizing the retinoic acid receptor antagonist AGN194310.

摘要

这项工作描述了 -芳基丙炔基硫化物的 6-环化反应，以得到 2-硫代色烯。炔丙位的取代在允许银催化的炔烃氢芳基化和碘代琥珀酰亚胺促进的碘芳基化的分子内反应中起着关键作用。此外，还开发了 PTSA 催化的丙炔醇的硫代反应，以合成所需的叔 -芳基丙炔基醚。通过合成维甲酸受体拮抗剂 AGN194310，证明了合并这两种方法的适用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/c4207064df13/jo1c00333_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/cedcf55d2c0c/jo1c00333_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/ca1d60afcba6/jo1c00333_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/cc01061d8ec6/jo1c00333_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/d80c466f8238/jo1c00333_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/46a8b6302304/jo1c00333_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/01da2e92efe8/jo1c00333_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/c4207064df13/jo1c00333_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/cedcf55d2c0c/jo1c00333_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/ca1d60afcba6/jo1c00333_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/cc01061d8ec6/jo1c00333_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/d80c466f8238/jo1c00333_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/46a8b6302304/jo1c00333_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/01da2e92efe8/jo1c00333_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/654a/8474117/c4207064df13/jo1c00333_0007.jpg

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6
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