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Synthesis 2019; 51(11): 2331-2338
DOI: 10.1055/s-0037-1610868
paper
© Georg Thieme Verlag Stuttgart · New York

Trichloroisocyanuric Acid Induced Chlorine Radical Cascade Chlorination­/Carbocyclization of Acrylamides: Constructing Chlorinated Oxindoles by C–Cl and C–C Bond-Forming Reactions

Yingpeng Su  *
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Lindan Cao
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Ya Shi
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Yawei Feng
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Wenxuan Xue
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Guiyan Cao
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Ke-Hu Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Danfeng Huang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Congde Huo
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
,
Yulai Hu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: Suyp51@nwnu.edu.cn
b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
› Author AffiliationsWe are thankful for financial support from the National Natural Science Foundation of China (Grant No. 21502154, 21362033); and the Gansu Provincial Science and Technology Program (No. 17JR5RA073).
Further Information

Publication History

Received: 17 January 2019

Accepted after revision: 12 February 2019

Publication Date:
14 March 2019 (online)

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Abstract

A metal- and additive-free strategy for the synthesis of oxindoles has been achieved through a chlorine radical-induced cascade chlorination/carbocyclization of N-aryl acrylamides. Trichloroiso­cyanuric acid (TCCA) is used as both radical initiator and chlorine source. A wide range of substrates can be applied in this process to directly afford chlorinated oxindoles via C–Cl and C–C bond formation.

Key words

trichloroisocyanuric acid - N-aryl acrylamide - chlorination - cascade carbocyclization reaction - oxindoles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610868.
  • Supporting Information
 

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