Functionalized 4-Aminoquinolines by Rearrangement of Pyrazole N-Heterocyclic Carbenes

被引:67
作者
Schmidt, Andreas [1 ]
Muenster, Niels [1 ]
Dreger, Andrij [1 ]
机构
[1] Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany
关键词
carbenes; heterocycles; rearrangements; synthetic methods; zwitterions; STABLE 5-MEMBERED-RING ALLENES; MESOMERIC BETAINES; PALLADIUM(II) PYRAZOLIN-4-YLIDENES; CATALYTIC APPLICATION; COMPLEXES; DECARBOXYLATION; ALKALOIDS; CHEMISTRY; CARBOXYLATES; CONJUGATION;
D O I
10.1002/anie.200905436
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Thermal decarboxylation of 1-phenyl pyrazolium-3- carboxylates from the mesomeric betaine class of substances leads to pyrazole-N-heterocyclic carbenes, which immediately rearrange to multiply substituted 4-aminoquinolines (see scheme). These species are of interest for the synthesis of heterocycles and pharmacologically active compounds. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2790 / 2793
页数:4
相关论文
共 57 条
[1]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[2]   Stable Five-Membered-Ring Allenes with Second-Row Elements Only: Not Allenes, But Zwitterions [J].
Christl, Manfred ;
Engels, Bernd .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (09) :1538-1539
[3]   Stability and reactivity of N-heterocyclic carbene complexes [J].
Crudden, CM ;
Allen, DP .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2247-2273
[4]   Betaine Adducts of N-Heterocyclic Carbenes: Synthesis, Properties, and Reactivity [J].
Delaude, Lionel .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (13) :1681-1699
[5]   Structure-function relationships in aminoquinolines:: Effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of β-hematin formation, and antiplasmodial activity [J].
Egan, TJ ;
Hunter, R ;
Kaschula, CH ;
Marques, HM ;
Misplon, A ;
Walden, J .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (02) :283-291
[6]   Exocyclic Delocalization at the Expense of Aromaticity in 3,5-bis(π-Donor) Substituted Pyrazolium Ions and Corresponding Cyclic Bent Allenes [J].
Fernandez, Israel ;
Dyker, C. Adam ;
DeHope, Alan ;
Donnadieu, Bruno ;
Frenking, Gernot ;
Bertrand, Guy .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) :11875-11881
[7]  
Findlay GM, 1951, RECENT ADV CHEMOTHER
[8]  
Glorius F, 2007, TOP ORGANOMETAL CHEM, V21, P1, DOI 10.1007/3418_2006_059
[9]   Malaria in 2002 [J].
Greenwood, B ;
Mutabingwa, T .
NATURE, 2002, 415 (6872) :670-672
[10]  
Hahn F.E., 2008, Angew. Chem., V120, P3166