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Gold-catalyzed [5 + 2]-annulations of 1,3-diyn-1-amides with anthranils bearing no C(6)-substituents†
Yashwant Bhaskar Pandit,Yan-Ting Jiang,Jia-Jyun Jian,Tai-Chi Chen,Tung-Chun Kuo,Mu-Jeng Cheng,Rai-Shung Liu
Organic Chemistry Frontiers Pub Date : 03/16/2021 00:00:00 , DOI:10.1039/D1QO00026H
Abstract

This work reports the gold-catalyzed [5 + 2]-annulations of commonly used anthranils with 1,3-diynamides, yielding quiniline oxides as the main products. Previously, these [5 + 2]-annulations were operable only for ynamides and special anthranils bearing C(6)-substituents. The preferable chemoselectivity is attributed to the electron-withdrawing effects of aryltosylamides and alkynes, increasing the electrophilicity of the less hindered α-imino gold carbenes.

Graphical abstract: Gold-catalyzed [5 + 2]-annulations of 1,3-diyn-1-amides with anthranils bearing no C(6)-substituents
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