γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles

Mei-Huey Lin; Yen Chih Huang; Chung Kai Kuo; Chang Hsien Tsai; Yi Syuan Li; Ting Chia Hu; Tsung Hsun Chuang

doi:10.1021/jo5001274

γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles

Mei-Huey Lin, Yen Chih Huang, Chung Kai Kuo, Chang Hsien Tsai, Yi Syuan Li, Ting Chia Hu, Tsung Hsun Chuang

Department of Chemistry

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

11 Citations (Scopus)

Abstract

A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.

Original language	English
Pages (from-to)	2751-2757
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	79
Issue number	6
DOIs	https://doi.org/10.1021/jo5001274
Publication status	Published - 2014 Mar 21

All Science Journal Classification (ASJC) codes

Organic Chemistry

Access to Document

10.1021/jo5001274

Fingerprint Dive into the research topics of 'γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles'. Together they form a unique fingerprint.

Cite this

@article{e520ce21d01c4755a2c57eda2a4feaf1,

title = "γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles",

abstract = "A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.",

author = "Mei-Huey Lin and Huang, {Yen Chih} and Kuo, {Chung Kai} and Tsai, {Chang Hsien} and Li, {Yi Syuan} and Hu, {Ting Chia} and Chuang, {Tsung Hsun}",

year = "2014",

month = mar,

day = "21",

doi = "10.1021/jo5001274",

language = "English",

volume = "79",

pages = "2751--2757",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

}

γ-halo-enones : A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles. / Lin, Mei-Huey; Huang, Yen Chih; Kuo, Chung Kai; Tsai, Chang Hsien; Li, Yi Syuan; Hu, Ting Chia; Chuang, Tsung Hsun.

In: Journal of Organic Chemistry, Vol. 79, No. 6, 21.03.2014, p. 2751-2757.

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

TY - JOUR

T1 - γ-halo-enones

T2 - A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles

AU - Lin, Mei-Huey

AU - Huang, Yen Chih

AU - Kuo, Chung Kai

AU - Tsai, Chang Hsien

AU - Li, Yi Syuan

AU - Hu, Ting Chia

AU - Chuang, Tsung Hsun

PY - 2014/3/21

Y1 - 2014/3/21

N2 - A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.

AB - A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.

UR - http://www.scopus.com/inward/record.url?scp=84896979411&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84896979411&partnerID=8YFLogxK

U2 - 10.1021/jo5001274

DO - 10.1021/jo5001274

M3 - Article

AN - SCOPUS:84896979411

VL - 79

SP - 2751

EP - 2757

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 6

ER -