Organophosphorus-catalyzed diaza-Wittig reaction: application to the synthesis of pyridazines

被引:33
作者
Abed, Hassen Bel [1 ]
Mammoliti, Oscar [2 ]
Bande, Omprakash [1 ]
Van Lommen, Guy [2 ]
Herdewijn, Piet [1 ]
机构
[1] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Leuven, Belgium
[2] Galapagos NV, Med Chem Lab, B-2800 Mechelen, Belgium
关键词
DIELS-ALDER REACTIONS; CONVENIENT STRATEGY; APPEL; DERIVATIVES;
D O I
10.1039/c4ob01201a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The elaboration of the first organophosphorus-catalyzed diaza-Wittig reaction is reported. This catalytic reaction is applied to the synthesis of substituted pyridazine and phthalazine derivatives bearing electron-withdrawing groups with good to excellent yields from substrates containing a diazo functionality as the starting material and a phospholene oxide as the catalyst.
引用
收藏
页码:7159 / 7166
页数:8
相关论文
共 52 条
[21]   A novel approach to functionalised pyridazinone arrays [J].
Helm, Matthew D. ;
Plant, Andrew ;
Harrity, Joseph P. A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) :4278-4280
[22]   Synthesis of highly substituted pyridazines through alkynyl boronic ester cycloaddition reactions [J].
Helm, MD ;
Moore, JE ;
Plant, A ;
Harrity, JPA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3889-3892
[23]   Stereospecific reduction of phosphine oxides to phosphines by the use of a methylation reagent and lithium aluminum hydride [J].
Imamoto, T ;
Kikuchi, S ;
Miura, T ;
Wada, Y .
ORGANIC LETTERS, 2001, 3 (01) :87-90
[24]  
Johnson A.W., 1993, YLIDES IMINES PHOSPH
[25]  
Krber N., 2010, SYNLETT, P782
[26]  
Kutkovaya N. V., 2003, ZH ORG KHIM, V39, P1713
[27]  
Kutkovaya N. V., 2004, ZH ORG KHIM, V40, P1078
[28]   Triphenylphosphine-catalysed amide bond formation between carboxylic acids and amines [J].
Lenstra, Danny C. ;
Rutjes, Floris P. J. T. ;
Mecinovic, Jasmin .
CHEMICAL COMMUNICATIONS, 2014, 50 (43) :5763-5766
[29]   Organocatalytic One- Pot Synthesis of Highly Substituted Pyridazines from Morita- Baylis- Hillman Carbonates and Diazo Compounds [J].
Mao, Haibin ;
Lin, Aijun ;
Tang, Zhongkai ;
Hu, Hongwen ;
Zhu, Chengjian ;
Cheng, Yixiang .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (09) :2454-2458
[30]   Catalytic aza-Wittig cyclizations for heteroaromatic synthesis [J].
Marsden, Stephen P. ;
McGonagle, Alison E. ;
McKeever-Abbas, Ben .
ORGANIC LETTERS, 2008, 10 (12) :2589-2591