Synthesis of Tribenzotropone by Ring Expansion of Phenanthrene-9,10-dione

被引：3

作者：

Choi, Jeongae ^{[1
]}

Jung, Hyunuk ^{[1
]}

Yeo, Jeong-Eun ^{[2
]}

Koo, Sangho ^{[1
,2
]}

机构：

[1] Myong Ji Univ, Dept Energy & Biotechnol, Yongin 449728, Gyeonggi Do, South Korea

[2] Myong Ji Univ, Dept Chem, Yongin 449728, Gyeonggi Do, South Korea

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 19期

关键词：

annulations; cycloadditions; Diels-Alder reactions; fused-ring systems; ring expansion; LIQUID-CRYSTALS;

D O I：

10.1055/s-0034-1381045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tribenzotropone was efficiently synthesized by a ring-expansion method from readily available phenanthrene-9,10-dione via a ring-opened diketone as a key intermediate; the diketone was prepared by nucleophilic addition of allyl and vinyl groups, followed by an oxidative ring-opening reaction with lead(IV) acetate. Ring closure by an intra-molecular Diels-Alder reaction and subsequent dehydrogenation produced tribenzotropone in 38% overall yield. Ring closure by a Morita-Baylis-Hillman reaction, on the other hand, produced a dibenzo-fused nonanedione in 22% overall yield.

引用

页码：2957 / 2960

页数：4

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