Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones

被引：4

作者：

Lu, Shengle

Tu, Xianxia

Liu, Weishun

Shen, Liting

Mao, Shanjian

Deng, Guisheng ^{[1
]}

机构：

[1] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 38卷 / 07期

基金：

中国国家自然科学基金;

关键词：

diazo gamma-pyrone; diazo 3(2H)-furanone; synthesis; cyclopropanation; regioselectivity; BIOLOGICAL EVALUATION; RING-CLOSURE; DERIVATIVES; INHIBITORS; ACIDS; POTENT; 6-ENDO-DIG; ANNULATION; FLAVONES; KETONES;

D O I：

10.6023/cjoc201712014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

For HSbF6/EtOH system, diazo gamma-pyrones were cleanly obtained starting from 2-diazo-3,5-dioxo-6-ynoates/ynones/ynamide at 80 degrees C, whereas diazo 3(2H)-furanones were predominantly generated in HOAc-Et3N-1,2-dichloroethane system at 25 degrees C. These diazo compounds can undergo an efficient Rh(II)-catalyzed intermolecular cyclopropanation with alkene.

引用

页码：1663 / 1672

页数：10

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