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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

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 Brønsted acids.

Original language	English
Pages (from-to)	1561-1571
Number of pages	11
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	8
DOIs	https://doi.org/10.1002/ajoc.201900292
State	Published - Aug 2019

Keywords

alkynes
cascade reactions
cyclization
Friedel-Crafts
indenes

Access to Document

10.1002/ajoc.201900292

Electrified Interfaces at the Nanometer Scale(III)
Yau, S.
1/08/18 → 31/07/19
Project: Research

CCDC 1898770: Experimental Crystal Structure Determination
Kotipalli, T. (Contributor) & Hou, D. (Contributor), 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
Dataset

Cite this

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

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

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

year = "2019",

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doi = "10.1002/ajoc.201900292",

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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 - alkynes

KW - cascade reactions

KW - cyclization

KW - Friedel-Crafts

KW - indenes

UR - http://www.scopus.com/inward/record.url?scp=85067520208&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201900292

DO - 10.1002/ajoc.201900292

M3 - 期刊論文

AN - SCOPUS:85067520208

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

Abstract

Keywords

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Projects

Electrified Interfaces at the Nanometer Scale(III)

Datasets

CCDC 1898770: Experimental Crystal Structure Determination

Cite this