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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Copper-Catalyzed Oxidative (4 + 2) Cycloaddition of 2-Arylindoles and 2-Aminophenols To Prepare Indole-Fused
Wei-Min Shi1, Pei-Sen Zou2, Ke Huang1
1School of Medicine, Guangxi University of Science and Technology, 2 Wenchang Road, Liuzhou 545006, China.
Abstract:
Herein, we reported a copper(I)-catalyzed oxidative (4 + 2) cycloaddition of 2-aryl indoles and 2-aminophenols to prepare a variety of indole-fused 1,4-benzoxazines containing a quaternary carbon stereocenter in moderate to excellent yields in the presence of t-butyl nitrite (TBN) as an oxidant. Mechanistic studies indicated that the reaction involved a TBN-mediated nitrosation, copper-catalyzed condensation, and subsequent intramolecular cyclization in a one pot. Moreover, the obtained indole-fused 1,4-benzoxazine can be easily converted into angularly fused 6-5-5 tricyclic scaffold in a total 50% yield over two steps.
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