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Synthesis 2019; 51(11): 2331-2338
DOI: 10.1055/s-0037-1610868
DOI: 10.1055/s-0037-1610868
paper
Trichloroisocyanuric Acid Induced Chlorine Radical Cascade Chlorination/Carbocyclization of Acrylamides: Constructing Chlorinated Oxindoles by C–Cl and C–C Bond-Forming Reactions
We 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)
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 - oxindolesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610868.
- Supporting Information
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