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DMAP-catalyzed alkylation of isatin N,N′-cyclic azomethine imine 1,3-dipoles with Morita–Baylis–Hillman carbonates

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Abstract

Azomethine imines are valuable substrates in catalysis, and can be precursors to complex 3-substituted oxindoles. An efficient and convenient synthetic approach to azomethine imines is developed via DMAP-catalyzed direct alkylation at the α-position of the cyclic amine of the new isatin N,N′-cyclic azomethine imines with Morita–Baylis–Hillman carbonates. A variety of α-alkylated-isatin N,N′-cyclic azomethine imine 1,3-dipoles were obtained in excellent yields (up to 99%) under mild conditions.

Graphical abstract: DMAP-catalyzed alkylation of isatin N,N′-cyclic azomethine imine 1,3-dipoles with Morita–Baylis–Hillman carbonates

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Publication details

The article was received on 15 Jan 2018, accepted on 27 Mar 2018 and first published on 28 Mar 2018


Article type: Paper
DOI: 10.1039/C8NJ00234G
Citation: New J. Chem., 2018, Advance Article
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    DMAP-catalyzed alkylation of isatin N,N′-cyclic azomethine imine 1,3-dipoles with Morita–Baylis–Hillman carbonates

    S. Hu, J. Zhang and Q. Jin, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ00234G

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