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

Organic & Biomolecular Chemistry
Na FeiZhu-Jun Yao

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.

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Citations

Aug 2, 2011·Beilstein Journal of Organic Chemistry·Sara Hummel, Stefan F Kirsch
Dec 20, 2016·The Journal of Organic Chemistry·Patricia García-GarcíaRoberto Sanz
Jan 21, 2012·Organic & Biomolecular Chemistry·Yan LiRoman Dembinski
Jan 18, 2014·Organic & Biomolecular Chemistry·Mahalingam Sivaraman, Paramasivan T Perumal
Aug 23, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jiaqi YuanChunhao Yang
Apr 22, 2011·Organic & Biomolecular Chemistry·T Krishna Chaitanya, Rajagopal Nagarajan
Sep 19, 2012·Organic & Biomolecular Chemistry·Adeline Palisse, Stefan F Kirsch
Apr 11, 2012·Chemistry : a European Journal·Prakash T ParvatkarSantosh G Tilve
Sep 23, 2014·The Journal of Organic Chemistry·Hao YinZhu-Jun Yao

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