Ruthenium-Catalyzed Regioselective Alkenylation/Tandem Hydroamidative Cyclization of Unmasked Quinazolinones Using Terminal Alkynes

被引：25

作者：

Viveki, Amol B. ^{[1
,2
]}

Mhaske, Santosh B. ^{[1
,2
]}

机构：

[1] Natl Chem Lab, CSIR, Div Organ Chem, Pune 411008, Maharashtra, India

[2] Natl Chem Lab, CSIR, Acad Sci & Innovat Res AcSIR, Pune 411008, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期

关键词：

CASCADE SYNTHESIS; DIRECTING GROUP; QUINAZOLIN-4(3H)-ONES; FUNCTIONALIZATION; HYDROARYLATION; BONDS; DIVERSIFICATION; HETEROARENES; CHEMISTRY; ALKENES;

D O I：

10.1021/acs.joc.8b01143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ruthenium-catalyzed amide directed C-sp2-H activation of the quinazolinone scaffold has been demonstrated, leading to the selective mono- or dialkenylation in moderate to good yields to achieve medicinally important stilbene containing quinazolinones. The terminal allcyne is utilized as a coupling partner, which resulted in the selective trans-alkene formation. Electron-deficient phenylacetylenes facilitate alkenylation followed by tandem hydroamidation of the newly generated trans double bond to provide novel quinazolinone alkaloids related to the Luotonine class of natural products.

引用

页码：8906 / 8913

页数：8

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