Silver-Catalyzed Annulation of Arynes with Nitriles for Synthesis of Structurally Diverse Quinazolines

被引：22
作者：
Ghorai, Sourav [1 ]
Lin, Yongjia [2 ]
Xia, Yuanzhi [2 ]
Wink, Donald J. [1 ]
Lee, Daesung [1 ]
机构：
[1] Univ Illinois, Dept Chem, 845 West Taylor St, Chicago, IL 60607 USA
[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 02期
关键词：
2 DISCRETE NITRILES; ALDER-ENE REACTIONS; 2+2+2 CYCLOADDITIONS; DERIVATIVES; CYCLIZATIONS; ALKYNES; REGIOSELECTIVITIES; BIOACTIVITY; INHIBITORS; EFFICIENCY;
D O I：
10.1021/acs.orglett.9b04395
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient silver catalyzed annulation reaction of aryne with nitriles to generate quinazolines is described. Arynes generated from triynes or tetraynes through a hexadehydro Diels-Alder reaction readily participated in an [A + 2B] mode of annulation with nitriles in the presence of AgSbF6 catalyst. The mechanism was explored by DFT calculations, which supports the silver-catalyzed formation of nitrilium ion as a key intermediate. This annulation generates an array of polysubstituted novel quinazoline derivatives with excellent regioselectivity.
引用
收藏
页码：626 / 630
页数：5
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