Gold-Catalyzed Concomitant [3 + 3] Cycloaddition/Cascade Heterocyclization of Enynones/Enynals with Azides Leading to Furanotriazines

The Journal of Organic Chemistry
A Leela Siva Kumari, K C Kumara Swamy

Abstract

[Au]-catalyzed [3 + 3] cycloaddition reaction of enynones/enynals with azides, which allows the efficient regioselective synthesis of highly fused furo[3,4-d][1,2,3]triazines in good-to-excellent yields under mild conditions, has been developed. The synthetic utility of furanotriazines was exploited by oxidation with cerium ammonium nitrate (CAN) affording highly functionalized dihydrotriazines. Both furo[3,4-d][1,2,3]triazines and dihydrotriazines exhibit good fluorescence activity.

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Citations

Jun 16, 2016·Organic & Biomolecular Chemistry·A Leela Siva KumariK C Kumara Swamy
Oct 11, 2016·Organic & Biomolecular Chemistry·Aurélien BlancPatrick Pale
Jan 1, 2017·Chemistry : a European Journal·Lucien D CaspersBoris J Nachtsheim
Oct 1, 2020·Organic & Biomolecular Chemistry·Xiaoze BaoHong Wang
Oct 3, 2017·Chemical Communications : Chem Comm·Stalin R PathipatiNicklas Selander
Feb 4, 2021·Angewandte Chemie·Violet Yijang Chen, Ohyun Kwon
Oct 2, 2020·Accounts of Chemical Research·Deyun Qian, Junliang Zhang

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