Silver-Catalyzed Annulation of Arynes with Nitriles for Synthesis of Structurally Diverse Quinazolines
Silver-Catalyzed Annulation of Arynes with Nitriles for Synthesis of Structurally Diverse Quinazolines
复制标题
银催化芳炔与腈的成环反应合成结构多样的喹唑啉
DOI：
10.1021/acs.orglett.9b04395
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发表时间：
2020-01-17
期刊：
影响因子：
5.2
通讯作者：
Lee, Daesung
中科院分区：
文献类型：
--
作者：
Ghorai, Sourav;Lin, Yongjia;Lee, Daesung
本文报道了一种高效的银催化芳炔与腈的成环反应。在AgSbF 6催化剂存在下，三炔或四炔经六氢Diels-Alder反应生成的芳炔与腈以[A + 2B]模式成环。通过密度泛函理论（DFT）计算对反应机理进行了探讨，结果支持银催化形成亚硝酸根离子为关键中间体的观点。这种环化反应生成了一系列具有优异区域选择性的多取代的新型喹唑啉衍生物。
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.