Sequential N-acylamide methylenation-enamide ring-closing metathesis:: Construction of benzo-fused nitrogen heterocycles

被引：66

作者：

Bennasar, M. Lluisa ^{[1
]}

Roca, Tomas ^{[1
]}

Monerris, Manuel ^{[1
]}

Garcia-Diaz, Davinia ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 18期

关键词：

D O I：

10.1021/jo061180j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis (RCM) step is complicated by the alkene isomerization processes. From certain substrates, the direct annulation is observed in the titanium-mediated step, which is likely to occur through an olefin metathesis-intramolecular olefination sequence.

引用

页码：7028 / 7034

页数：7

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