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
收藏
页码：7028 / 7034
页数：7
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