Synthesis of 3-Bromoindenes from 4-Alkynyl Alcohols/Sulfonamides and Aldehydes via Prins Cyclization, Ring-Opening and Friedel-Crafts Reactions

Trimurtulu Kotipalli; Duen Ren Hou

doi:10.1002/ajoc.201900292

Synthesis of 3-Bromoindenes from 4-Alkynyl Alcohols/Sulfonamides and Aldehydes via Prins Cyclization, Ring-Opening and Friedel-Crafts Reactions

Trimurtulu Kotipalli, Duen Ren Hou

化學學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

10 引文斯高帕斯（Scopus）

摘要

A one-pot, two-staged protocol has been developed for the synthesis of 3-bromoindenes from aryl alkynyl alcohols/sulfonamides and aldehydes. Bromotrimethylsilane (TMSBr) initiated a halo-Prins cyclization reaction to give 3-(bromomethylene)-tetrahydropyrans or -piperidines, which underwent ring-opening and Friedel-Crafts allylation to yield 3-bromoindenes in the presence of Brønsted acids.

原文	???core.languages.en_GB???
頁（從 - 到）	1561-1571
頁數	11
期刊	Asian Journal of Organic Chemistry
卷	8
發行號	8
DOIs	https://doi.org/10.1002/ajoc.201900292
出版狀態	已出版 - 8月 2019

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10.1002/ajoc.201900292

奈米尺度電化學界面的研究(3/3)
Yau, S.-L. (PI)
1/08/18 → 31/07/19
研究計畫: Research

CCDC 1898770: Experimental Crystal Structure Determination
Kotipalli, T. (貢獻者) & Hou, D.-R. (貢獻者), The Cambridge Structural Database, 2019
DOI: 10.5517/ccdc.csd.cc21qtn8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21qtn8&sid=DataCite
資料集

引用此

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title = "Synthesis of 3-Bromoindenes from 4-Alkynyl Alcohols/Sulfonamides and Aldehydes via Prins Cyclization, Ring-Opening and Friedel-Crafts Reactions",

abstract = "A one-pot, two-staged protocol has been developed for the synthesis of 3-bromoindenes from aryl alkynyl alcohols/sulfonamides and aldehydes. Bromotrimethylsilane (TMSBr) initiated a halo-Prins cyclization reaction to give 3-(bromomethylene)-tetrahydropyrans or -piperidines, which underwent ring-opening and Friedel-Crafts allylation to yield 3-bromoindenes in the presence of Br{\o}nsted acids.",

keywords = "Friedel-Crafts, alkynes, cascade reactions, cyclization, indenes",

author = "Trimurtulu Kotipalli and Hou, {Duen Ren}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Synthesis of 3-Bromoindenes from 4-Alkynyl Alcohols/Sulfonamides and Aldehydes via Prins Cyclization, Ring-Opening and Friedel-Crafts Reactions

AU - Kotipalli, Trimurtulu

AU - Hou, Duen Ren

PY - 2019/8

Y1 - 2019/8

N2 - A one-pot, two-staged protocol has been developed for the synthesis of 3-bromoindenes from aryl alkynyl alcohols/sulfonamides and aldehydes. Bromotrimethylsilane (TMSBr) initiated a halo-Prins cyclization reaction to give 3-(bromomethylene)-tetrahydropyrans or -piperidines, which underwent ring-opening and Friedel-Crafts allylation to yield 3-bromoindenes in the presence of Brønsted acids.

AB - A one-pot, two-staged protocol has been developed for the synthesis of 3-bromoindenes from aryl alkynyl alcohols/sulfonamides and aldehydes. Bromotrimethylsilane (TMSBr) initiated a halo-Prins cyclization reaction to give 3-(bromomethylene)-tetrahydropyrans or -piperidines, which underwent ring-opening and Friedel-Crafts allylation to yield 3-bromoindenes in the presence of Brønsted acids.

KW - Friedel-Crafts

KW - alkynes

KW - cascade reactions

KW - cyclization

KW - indenes

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U2 - 10.1002/ajoc.201900292

DO - 10.1002/ajoc.201900292

M3 - 期刊論文

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SN - 2193-5807

VL - 8

SP - 1561

EP - 1571

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 8

ER -

Synthesis of 3-Bromoindenes from 4-Alkynyl Alcohols/Sulfonamides and Aldehydes via Prins Cyclization, Ring-Opening and Friedel-Crafts Reactions

摘要

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指紋

專案

奈米尺度電化學界面的研究(3/3)

資料集

CCDC 1898770: Experimental Crystal Structure Determination

引用此