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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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 & Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Jiangxi Province, Nanchang 330013, ChinaInstitute of Organic Chemistry, Jiangxi Science & 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 |
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