An electrophilic thiocyanation/ipso-cyclization leading to spirocyclohexadienones

Zhihua Qiao; Chukai Shao; Yong Gao; Kun Liang; Hongquan Yin; Fu Xue Chen

doi:10.1016/j.tetlet.2022.153875

An electrophilic thiocyanation/ipso-cyclization leading to spirocyclohexadienones

Zhihua Qiao, Chukai Shao, Yong Gao, Kun Liang, Hongquan Yin, Fu Xue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

8 Citations (Scopus)

Abstract

A Lewis acid-catalyzed cyclization of N-(p-methoxyphenyl)-3-phenylpropionamide with N-thiocyanosuccinimide has been accomplished under mild conditions. Thus, a series of thiocyanato-containing spirocyclohexadienones was obtained in moderate to excellent yields with a good functional group tolerance and a wide range of substrates. It provides an alternative approach for the synthesis of functionalized spirocyclohexadienones.

Original language	English
Article number	153875
Journal	Tetrahedron Letters
Volume	100
DOIs	https://doi.org/10.1016/j.tetlet.2022.153875
Publication status	Published - 22 Jun 2022

Keywords

Dearomatization
Electrophilic thiocyanation
Ipso-Cyclization
Spirocyclohexadienones

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10.1016/j.tetlet.2022.153875

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title = "An electrophilic thiocyanation/ipso-cyclization leading to spirocyclohexadienones",

abstract = "A Lewis acid-catalyzed cyclization of N-(p-methoxyphenyl)-3-phenylpropionamide with N-thiocyanosuccinimide has been accomplished under mild conditions. Thus, a series of thiocyanato-containing spirocyclohexadienones was obtained in moderate to excellent yields with a good functional group tolerance and a wide range of substrates. It provides an alternative approach for the synthesis of functionalized spirocyclohexadienones.",

keywords = "Dearomatization, Electrophilic thiocyanation, Ipso-Cyclization, Spirocyclohexadienones",

author = "Zhihua Qiao and Chukai Shao and Yong Gao and Kun Liang and Hongquan Yin and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} 2022",

year = "2022",

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doi = "10.1016/j.tetlet.2022.153875",

language = "English",

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T1 - An electrophilic thiocyanation/ipso-cyclization leading to spirocyclohexadienones

AU - Qiao, Zhihua

AU - Shao, Chukai

AU - Gao, Yong

AU - Liang, Kun

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2022/6/22

Y1 - 2022/6/22

N2 - A Lewis acid-catalyzed cyclization of N-(p-methoxyphenyl)-3-phenylpropionamide with N-thiocyanosuccinimide has been accomplished under mild conditions. Thus, a series of thiocyanato-containing spirocyclohexadienones was obtained in moderate to excellent yields with a good functional group tolerance and a wide range of substrates. It provides an alternative approach for the synthesis of functionalized spirocyclohexadienones.

AB - A Lewis acid-catalyzed cyclization of N-(p-methoxyphenyl)-3-phenylpropionamide with N-thiocyanosuccinimide has been accomplished under mild conditions. Thus, a series of thiocyanato-containing spirocyclohexadienones was obtained in moderate to excellent yields with a good functional group tolerance and a wide range of substrates. It provides an alternative approach for the synthesis of functionalized spirocyclohexadienones.

KW - Dearomatization

KW - Electrophilic thiocyanation

KW - Ipso-Cyclization

KW - Spirocyclohexadienones

UR - http://www.scopus.com/inward/record.url?scp=85130539972&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2022.153875

DO - 10.1016/j.tetlet.2022.153875

M3 - Article

AN - SCOPUS:85130539972

SN - 0040-4039

VL - 100

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153875

ER -

An electrophilic thiocyanation/ipso-cyclization leading to spirocyclohexadienones

Abstract

Keywords

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