Silver(i)-catalyzed selective hydroalkoxylation of C2-alkynyl quinazolinones to synthesize quinazolinone-fused eight-membered N,O-heterocycles

被引：27

作者：

Kong, Xiang-Fei ^{[1
,2
,3
]}

Guo, Xiu-Yun ^{[1
,2
]}

Gu, Zi-Yu ^{[1
,2
]}

Wei, Lin-Su ^{[1
,2
]}

Liu, Lu-Lu ^{[1
,2
]}

Mo, Dong-Liang ^{[1
,2
]}

Pan, Cheng-Xue ^{[1
,2
]}

Su, Gui-Fa ^{[1
,2
]}

机构：

[1] Guangxi Normal Univ, State Key Lab Chem & Mol Engn Med Resources, Minist Sci & Technol China, 15 Yu Cai Rd, Guilin 541004, Peoples R China

[2] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, 15 Yu Cai Rd, Guilin 541004, Peoples R China

[3] Guilin Univ Technol, Coll Chem & Bioengn, 12 Jian Gan Rd, Guilin 541004, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 15期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

MEDIUM-SIZED RINGS; NITRIC-OXIDE; ONE-POT; CYCLOADDITION; EXPANSION; REARRANGEMENT; RUTAECARPINE; CONSTRUCTION; HETEROCYCLES; CYCLIZATIONS;

D O I：

10.1039/d0qo00437e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2055 / 2062

页数：8

共 70 条

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