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Issue 24, 2014
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Cascade nitrosation and addition–elimination of nitroacetanilides for the highly efficient synthesis of 1,4,2,5-dioxadiazine derivatives

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Abstract

A domino nitrosation and addition–elimination of nitroacetanilides with NaNO2 and H2SO4 has been developed to synthesize a variety of 1,4,2,5-dioxadiazine-3,6-dicarboxamides in excellent yields. The substrate scope can be extended to aryl nitromethyl ketones. A cascade reaction mechanism is proposed and the conjugated aryl moiety is considered to help stabilize the aci-nitroso species, the key intermediates in the cascade reaction. The methodology is practical and efficient because it avoids the purification of the intermediates. The nitroacetanilides were prepared from nitroacetic acid and various anilines employing DCC–DMAP as coupling reagents, and this protocol also possesses advantages like easy handling and high yields.

Graphical abstract: Cascade nitrosation and addition–elimination of nitroacetanilides for the highly efficient synthesis of 1,4,2,5-dioxadiazine derivatives

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Publication details

The article was received on 12 Dec 2013, accepted on 01 Apr 2014 and first published on 02 Apr 2014


Article type: Paper
DOI: 10.1039/C3OB42487A
Citation: Org. Biomol. Chem., 2014,12, 4192-4200
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    Cascade nitrosation and addition–elimination of nitroacetanilides for the highly efficient synthesis of 1,4,2,5-dioxadiazine derivatives

    S. Mo, P. Huang and J. Xu, Org. Biomol. Chem., 2014, 12, 4192
    DOI: 10.1039/C3OB42487A

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