Step-Economical Route to 2-Amido-3-bromobenzo[b]thiophenes via Ynamide Formation and Selectfluor-Mediated Oxidative Bromocyclization

被引：4

作者：

Hong, Su Jeong ^{[1
,2
]}

Yoon, Chang Ju ^{[1
,4
]}

Lim, Hee Nam ^{[3
]}

Yeom, Hyun-Suk ^{[1
]}

机构：

[1] Korea Res Inst Chem Technol KRICT, Ecofriendly New Mat Res Ctr, Therapeut & Biotechnol Div, 141 Gajeong Ro, Daejeon 34114, South Korea

[2] Hanyang Univ, Dept Chem, 222 Wangsimni Ro, Seoul 04763, South Korea

[3] Yeungnam Univ, Dept Chem & Biochem, 280 Daehak Ro, Gyongsan 38541, Gyeongbuk, South Korea

[4] Sungkyunkwan Univ, Dept Chem, 2066 Seobu Ro, Suwon 16419, Gyeonggi Do, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 41期

基金：

新加坡国家研究基金会;

关键词：

Benzo[b]thiophenes; Cyclization; Selectfluor; Sulfur heterocycles; Ynamides; ELECTROPHILIC CYCLIZATION; RELATIVE POWER; EOSIN Y; FLUOROCYCLIZATION; BROMINATION; BENZOFURANS; ANNULATION; REAGENTS; ALCOHOLS; HALIDES;

D O I：

10.1002/ejoc.202101093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot synthesis of 2-amido-3-bromobenzo[b]thiophenes based on C-N coupling and oxidative bromocyclization reactions was developed. This enables a modular approach to obtain diverse substituents at the C2 position of benzothiophenes by employing structurally modified sulfonamides. Oxidative cyclization was driven by Selectfluor and represents a previously unreported recycling method for the bromide anion byproducts of the C-N bond coupling step. The details of the study are described fully herein.

引用

页码：5609 / 5617

页数：9