Synthesis of pyridazines functionalized with amino acid side chains

被引:10
作者
Mann, Enrique [1 ]
Moisan, Lionel [1 ]
Hou, Jun-Li [1 ]
Rebek, Julius, Jr. [1 ]
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
pyridazine; tetrazine; Tebbe reagent; inverse electron demand Diels-Alder reaction;
D O I
10.1016/j.tetlet.2007.11.149
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple route for the preparation of 3,4,6-substituted pyridazines is described by using Tebbe olefination of esters then Diels-Alder reaction of the resulting enol ethers with tetrazine. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:903 / 905
页数:3
相关论文
共 28 条
[1]   Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].
Akiyama, Takahiko ;
Morita, Hisashi ;
Fuchibe, Kohei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071
[2]   INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - 5H-PYRIDAZINO[4,5-B]INDOLES AS CYCLOADDUCTS WITH 3,6-DICARBOMETHOXY-1,2,4,5-TETRAZINE [J].
BENSON, SC ;
PALABRICA, CA ;
SNYDER, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4610-4614
[3]   Heterocyclic α-helix mimetics for targeting protein-protein interactions [J].
Biros, Shannon M. ;
Moisan, Lionel ;
Mann, Enrique ;
Carella, Alexandre ;
Zhai, Dayong ;
Reed, John C. ;
Rebek, Julius, Jr. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (16) :4641-4645
[5]  
BOGER DL, 1991, ORG SYNTH, V70, P79
[6]  
Cuccia LA, 2000, ANGEW CHEM INT EDIT, V39, P233, DOI 10.1002/(SICI)1521-3773(20000103)39:1<233::AID-ANIE233>3.0.CO
[7]  
2-R
[8]   The preparation of highly substituted pyridazines via a tethered imine-enamine (TIE) procedure [J].
Geyelin, Peter H. ;
Raw, Steven A. ;
Taylor, Richard J. K. .
ARKIVOC, 2007, :37-45
[9]  
Gnichtel H., 1985, LIEBIGS ANN CHEM, V3, P628
[10]   Synthesis of eosinophil infiltration inhibitors with antihistaminic activity [J].
Gyoten, M ;
Nagaya, H ;
Fukuda, S ;
Ashida, Y ;
Kawano, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (02) :122-133