Synthesis of Nitrogen-Containing Heterocycles via Ring-Closing Ene-Ene and Ene-Yne Metathesis Reactions: An Easy Access to 1-and 2-Benzazepine Scaffolds and Five- and Six-Membered Lactams

被引：11

作者：

Benedetti, Erica ^{[1
,2
]}

Lomazzi, Michela ^{[1
]}

Tibiletti, Francesco ^{[1
]}

Goddard, Jean-Philippe ^{[2
]}

Fensterbank, Louis ^{[2
]}

Malacria, Max ^{[2
]}

Palmisano, Giovanni ^{[1
]}

Penoni, Andrea ^{[1
]}

机构：

[1] Univ Insubria, Dipartimento Sci & Alta Tecnol, I-22100 Como, Italy

[2] Inst Parisien Chim Mol UMR CNRS 7201 FR 2769 UPMC, F-75005 Paris, France

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 22期

关键词：

ring closing ene-yne metathesis; ring closing ene-ene metathesis; Grubbs catalysts; nitrogen heterocycles; regioselective reactions; benzazepine scaffolds; lactams; AZA-CLAISEN REARRANGEMENT; SOLID-PHASE SYNTHESIS; ENYNE-METATHESIS; OLEFIN METATHESIS; TRYPANOSOMA-CRUZI; DERIVATIVES; CONSTRUCTION; INHIBITORS; DISCOVERY; POTENT;

D O I：

10.1055/s-0032-1317352

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel regioselective ring closing ene-yne metathesis provided an efficient access to different substituted 1-benzazepine scaffolds. The reported synthetic approach could also be used as a powerful tool for the selective formation of a highly functionalizable 2-benzazepine core. This synthetic protocol was even proved to be an efficient way to obtain a functionalizable benzazocine derivative. By modifying the structure of the starting materials, the optimized cyclization finally proved to be a suitable technique to obtain five-and six-membered lactams, enhancing the synthetic application of our method. Five-and six-membered lactams were efficiently prepared by ring-closing metathesis involving the loss of ethylene moiety and affording highly functionalizable compounds showing both electron-withdrawing substituents and electron-donor groups.

引用

页码：3523 / 3533

页数：11