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Updated: Jan 15, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of Chromeno[4,3-d][1,3]oxazines through Copper(I)-Catalyzed Cycloisomerization of 1,11-Enynes
Qing-Mei Li1, Zhang-Wei Liu1, Zi-Han Hu1
1Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi), School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
Abstract:
A copper(I)-catalyzed cycloisomerization of propargyl oxime-derived 1,11-enynes was developed to prepare various chromeno[4,3-d][1,3]oxazines containing two or three stereocenters in good yields with high regioselectivity and diastereoselectivity. Mechanistic studies revealed that the cycloisomerization of 1,11-enynes underwent copper-catalyzed 2,3-rearrangement, [3 + 2] cycloaddition, and 1,2-O migration in a one-pot reaction. The present method highlights a broad substrate scope and good functional group tolerance, the formation of two six-membered rings and two or three stereocenters, an unexcepted 1,2-O migration, and a novel chromeno[4,3-d][1,3]oxazine scaffold.
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