Silver(i)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles
Silver(i)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles
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银(i)催化C2-炔基喹唑啉酮选择性加氢烷氧基化合成喹唑啉酮稠合八元N,O-杂环
DOI：
10.1039/d0qo00437e
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发表时间：
2020-08-07
影响因子：
5.4
通讯作者：
Su, Gui-Fa
中科院分区：
文献类型：
--
作者：
Kong, Xiang-Fei;Guo, Xiu-Yun;Su, Gui-Fa
我们报道了银催化的c2 -炔基喹唑啉酮的氢烷氧基化，通过选择性8-内双环化，以优异的收率制备了一系列新的喹唑啉酮融合的八元N， o杂环。机理研究表明，银催化剂可能有助于亚胺基与炔的双齿配位，促进8-内双环形成八元N， o杂环。此外，所提出的双金属银中间体可能会促进在c2位置上具有末端炔的喹唑啉酮的氢烷氧基化。生物学评价表明，大多数设计的喹唑啉酮融合的八元N， o杂环明显抑制脂多糖刺激RAW264.7细胞中一氧化氮的产生，并显示出其作为潜在良好抗炎剂的生物活性。
We report a silver-catalyzed hydroalkoxylation of C2-alkynyl quinazolinones to prepare a series of novel quinazolinone-fused eight-membered N,O-heterocycles in good-to-excellent yields through a selective8-endo-digcyclization. Mechanistic studies revealed that the silver catalyst might aid bidentate coordination of an imine group and alkyne to facilitate 8-endo-digcyclization to afford eight-membered N,O-heterocycles. Also, the proposed bimetal silver intermediates might promote hydroalkoxylation rapidly for quinazolinones bearing terminal alkynes at the C2-position. Biological evaluations revealed that most of the designed quinazolinone-fused eight-membered N,O-heterocycles inhibited nitric-oxide generation significantly in lipopolysaccharide-stimulated RAW264.7 cells and displayed their bioactivity as potentially good anti-inflammatory agents.