Free Radical Cyclization of N -Arylacrylamides: Mild and Facile Synthesis of 3-Thiocyanato Oxindoles

Pran Gopal Karmaker; Jiashen Qiu; Di Wu; Hongquan Yin; Fu Xue Chen

doi:10.1055/s-0036-1591927

Free Radical Cyclization of N -Arylacrylamides: Mild and Facile Synthesis of 3-Thiocyanato Oxindoles

Pran Gopal Karmaker, Jiashen Qiu, Di Wu, 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

19 Citations (Scopus)

Abstract

A novel and convenient oxidative radical cyclization of N-substituted N -arylacrylamides for the synthesis of 3-thiocyanated oxindoles has been developed by using AgSCN and K ₂ S ₂ O ₈ as the radical source. This process allows a consistent and convenient access to SCN-containing heterocycles bearing a broad range of functional groups in good to excellent yields (up to 91%). Moreover, the use of inexpensive and readily available starting materials, operational simplicity, and excellent functional group tolerance makes this protocol practically attractive.

Original language	English
Article number	st-2017-w0859-l
Pages (from-to)	954-958
Number of pages	5
Journal	Synlett
Volume	29
Issue number	7
DOIs	https://doi.org/10.1055/s-0036-1591927
Publication status	Published - 23 Apr 2018

Keywords

alkenes
oxindole
radical cyclization
silver
tandem reaction
thiocyanation

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10.1055/s-0036-1591927

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abstract = "A novel and convenient oxidative radical cyclization of N-substituted N -arylacrylamides for the synthesis of 3-thiocyanated oxindoles has been developed by using AgSCN and K 2 S 2 O 8 as the radical source. This process allows a consistent and convenient access to SCN-containing heterocycles bearing a broad range of functional groups in good to excellent yields (up to 91%). Moreover, the use of inexpensive and readily available starting materials, operational simplicity, and excellent functional group tolerance makes this protocol practically attractive.",

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author = "Karmaker, {Pran Gopal} and Jiashen Qiu and Di Wu and Hongquan Yin and Chen, {Fu Xue}",

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T2 - Mild and Facile Synthesis of 3-Thiocyanato Oxindoles

AU - Karmaker, Pran Gopal

AU - Qiu, Jiashen

AU - Wu, Di

AU - Yin, Hongquan

AU - Chen, Fu Xue

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart, New York.

PY - 2018/4/23

Y1 - 2018/4/23

N2 - A novel and convenient oxidative radical cyclization of N-substituted N -arylacrylamides for the synthesis of 3-thiocyanated oxindoles has been developed by using AgSCN and K 2 S 2 O 8 as the radical source. This process allows a consistent and convenient access to SCN-containing heterocycles bearing a broad range of functional groups in good to excellent yields (up to 91%). Moreover, the use of inexpensive and readily available starting materials, operational simplicity, and excellent functional group tolerance makes this protocol practically attractive.

AB - A novel and convenient oxidative radical cyclization of N-substituted N -arylacrylamides for the synthesis of 3-thiocyanated oxindoles has been developed by using AgSCN and K 2 S 2 O 8 as the radical source. This process allows a consistent and convenient access to SCN-containing heterocycles bearing a broad range of functional groups in good to excellent yields (up to 91%). Moreover, the use of inexpensive and readily available starting materials, operational simplicity, and excellent functional group tolerance makes this protocol practically attractive.

KW - alkenes

KW - oxindole

KW - radical cyclization

KW - silver

KW - tandem reaction

KW - thiocyanation

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DO - 10.1055/s-0036-1591927

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IS - 7

M1 - st-2017-w0859-l

ER -

Free Radical Cyclization of N -Arylacrylamides: Mild and Facile Synthesis of 3-Thiocyanato Oxindoles

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Keywords

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