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Issue 18, 2010
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Azaanthraquinone assembly from N-propargylamino quinone via iodine-induced 6-endo-dig electrophilic cyclization

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Abstract

An efficient methodology taking advantage of the excellent nucleophilicity of aminoquinone to assemble the azaanthraquinone framework was developed via an iodine-induced 6-endo-dig electrophilic cyclization. Therefore, starting from N-propargylaminoquinones, various 3-iodo-1-azaanthraquinones were obtained in yields ranging from 45% to 90%. The metal-free protocol features facile installation of an iodine atom on the azaanthraquinone ring and benign functional group compatibility.

Graphical abstract: Azaanthraquinone assembly from N-propargylamino quinone via iodine-induced 6-endo-dig electrophilic cyclization

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Publication details

The article was received on 06 Apr 2010, accepted on 17 Jun 2010 and first published on 23 Jul 2010


Article type: Paper
DOI: 10.1039/C004896H
Org. Biomol. Chem., 2010,8, 4096-4103

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    Azaanthraquinone assembly from N-propargylamino quinone via iodine-induced 6-endo-dig electrophilic cyclization

    N. Fei, Q. Hou, S. Wang, H. Wang and Z. Yao, Org. Biomol. Chem., 2010, 8, 4096
    DOI: 10.1039/C004896H

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