Synthesis of Azaheterocyclic Vinylphosphonates by Ring-Closing Metathesis

被引:12
作者
Garzon, Cecile [1 ]
Attolini, Mireille [1 ]
Maffei, Michel [1 ]
机构
[1] Aix Marseille Univ, CNRS, ISm2, UMR 7313, F-13397 Marseille, France
关键词
Nitrogen heterocycles; Organocatalysis; Metathesis; Phosphorus; Ruthenium; OLEFIN METATHESIS; MANNICH REACTION; BETA-AMINO; ACID; INHIBITORS; PHOSPHORUS; ROUTE; ISOMERIZATION; HETEROCYCLES; DERIVATIVES;
D O I
10.1002/ejoc.201300375
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compounds were synthesized by ruthenium-catalyzed ring-closing metathesis of N-tosyl-N-(-alkenyl)aminomethylvinyl phosphonates, which were obtained from N-(-alkenyl)-N-tosylamides. These compounds, in turn, were prepared from unsaturated alcohols through the Mitsunobu reaction. This methodology gives access to five- and six-membered ring compounds. Additionally, chiral phosphonates can be obtained easily.
引用
收藏
页码:3653 / 3657
页数:5
相关论文
共 49 条
[1]   Potent anti-inflammatory activity of 3-aminovinylphosphonates as inhibitors of reactive oxygen intermediates, nitric oxides generation, and tumor necrosis factor-alpha release [J].
Al Quntar, Abed Al Aziz ;
Gallily, Ruth ;
Katzavian, Galia ;
Srebnik, Morris .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2007, 556 (1-3) :9-13
[2]   Searching for the Hidden Hydrides: The Competition between Alkene Isomerization and Metathesis with Grubbs Catalysts [J].
Ashworth, Ian W. ;
Hillier, Ian H. ;
Nelson, David J. ;
Percy, Jonathan M. ;
Vincent, Mark A. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (29) :5673-5677
[3]   The Cl2(PCy3)(IMes)Ru(=CHPh) catalyst:: olefin metathesis versus olefin isomerization [J].
Bourgeois, D ;
Pancrazi, A ;
Nolan, SP ;
Prunet, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 :247-252
[4]  
Brown RCD, 2006, HETEROCYCLES, V70, P705
[5]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[6]  
Cho J, 2003, IEEE NETWORK, V17, P5
[7]  
Dai LZ, 2008, CHEM-EUR J, V14, P7011, DOI [10.1002/chem.200701954, 10.1002/chern.200701954]
[8]   A detailed investigation of the aza-Prins reaction [J].
Dobbs, Adrian P. ;
Guesne, Sebastien J. J. ;
Parker, Robert J. ;
Skidmore, John ;
Stephenson, Richard A. ;
Hursthouse, Mike B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (05) :1064-1080
[9]   Ring-closing metathesis: Novel routes to aromatic heterocycles [J].
Donohoe, Timothy J. ;
Fishlock, Lisa P. ;
Procopiou, Panayiotis A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (19) :5716-5726
[10]   Enamide-Benzyne-[2+2] Cycloaddition: Stereoselective Tandem [2+2]-Pericyclic Ring-Opening-Intramolecular N-Tethered [4+2] Cycloadditions [J].
Feltenberger, John B. ;
Hayashi, Ryuji ;
Tang, Yu ;
Babiash, Eric S. C. ;
Hsung, Richard P. .
ORGANIC LETTERS, 2009, 11 (16) :3666-3669