TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications

TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications

Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared <i>ortho</i>-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups com...

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Main Authors: Fengyan Jin, Tao Yang, Xian-Rong Song, Jiang Bai, Ruchun Yang, Haixin Ding, Qiang Xiao
Format: Article
Language:English
Published: MDPI AG 2019-11-01
Series:Molecules
Subjects:
tmsbr
propargylic alcohols
azides
cascade cyclization
4-bromo quinolines
Online Access:https://www.mdpi.com/1420-3049/24/21/3999
id doaj-9101305e83304151a142fb05315e9358
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spelling doaj-9101305e83304151a142fb05315e93582020-11-25T02:12:44ZengMDPI AGMolecules1420-30492019-11-012421399910.3390/molecules24213999molecules24213999TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its ApplicationsFengyan Jin0Tao Yang1Xian-Rong Song2Jiang Bai3Ruchun Yang4Haixin Ding5Qiang Xiao6Institute of Organic Chemistry, Jiangxi Science &amp; Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science &amp; Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science &amp; Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science &amp; Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science &amp; Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science &amp; Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science &amp; Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaDifficult-to-access 4-bromo quinolines are constructed directly from easily prepared <i>ortho</i>-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups compatibility. Notably, TMSBr not only acted as an acid-promoter to initiate the reaction, and also as a nucleophile. In addition, 4-bromo quinolines as key intermediates could further undergo the coupling reactions or nucleophilic reactions to provide a variety of functionalized compounds with molecular diversity at C4 position of quinolines.https://www.mdpi.com/1420-3049/24/21/3999tmsbrpropargylic alcoholsazidescascade cyclization4-bromo quinolines
collection DOAJ
language English
format Article
sources DOAJ
author Fengyan Jin
Tao Yang
Xian-Rong Song
Jiang Bai
Ruchun Yang
Haixin Ding
Qiang Xiao
spellingShingle Fengyan Jin
Tao Yang
Xian-Rong Song
Jiang Bai
Ruchun Yang
Haixin Ding
Qiang Xiao
TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
Molecules
tmsbr
propargylic alcohols
azides
cascade cyclization
4-bromo quinolines
author_facet Fengyan Jin
Tao Yang
Xian-Rong Song
Jiang Bai
Ruchun Yang
Haixin Ding
Qiang Xiao
author_sort Fengyan Jin
title TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
title_short TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
title_full TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
title_fullStr TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
title_full_unstemmed TMSBr-Promoted Cascade Cyclization of <i>ortho</i>-Propynol Phenyl Azides for the Synthesis of 4-Bromo Quinolines and Its Applications
title_sort tmsbr-promoted cascade cyclization of <i>ortho</i>-propynol phenyl azides for the synthesis of 4-bromo quinolines and its applications
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-11-01
description Difficult-to-access 4-bromo quinolines are constructed directly from easily prepared <i>ortho</i>-propynol phenyl azides using TMSBr as acid-promoter. The cascade transformation performs smoothly to generate desired products in moderate to excellent yields with good functional groups compatibility. Notably, TMSBr not only acted as an acid-promoter to initiate the reaction, and also as a nucleophile. In addition, 4-bromo quinolines as key intermediates could further undergo the coupling reactions or nucleophilic reactions to provide a variety of functionalized compounds with molecular diversity at C4 position of quinolines.
topic tmsbr
propargylic alcohols
azides
cascade cyclization
4-bromo quinolines
url https://www.mdpi.com/1420-3049/24/21/3999
work_keys_str_mv AT fengyanjin tmsbrpromotedcascadecyclizationofiorthoipropynolphenylazidesforthesynthesisof4bromoquinolinesanditsapplications
AT taoyang tmsbrpromotedcascadecyclizationofiorthoipropynolphenylazidesforthesynthesisof4bromoquinolinesanditsapplications
AT xianrongsong tmsbrpromotedcascadecyclizationofiorthoipropynolphenylazidesforthesynthesisof4bromoquinolinesanditsapplications
AT jiangbai tmsbrpromotedcascadecyclizationofiorthoipropynolphenylazidesforthesynthesisof4bromoquinolinesanditsapplications
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AT qiangxiao tmsbrpromotedcascadecyclizationofiorthoipropynolphenylazidesforthesynthesisof4bromoquinolinesanditsapplications
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