Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides

被引:83
作者
Bossharth, E
Desbordes, P
Monteiro, N
Balme, G
机构
[1] Univ Lyon 1, CNRS, UMR 5622, Lab Chim Organ 1, F-69622 Villeurbanne, France
[2] Bayer CropSci, F-69623 Lyon, France
关键词
D O I
10.1021/ol034644y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic The one-pot assembly of 4-alkoxy-3-iodo-2-pyridones, terminal alkynes, and organic halides has been achieved by integration of two sequential palladium-mediated cross-coupling reactions-Sonogashira and Wacker-type heteroannulation processes-and subsequent deprotection of the alkoxy group to afford furo[2,3-b]pyridones.
引用
收藏
页码:2441 / 2444
页数:4
相关论文
共 52 条
[41]   Controlling chemoselectivity in vinyl and allylic C-X bond activation with palladium catalysis:: A pKa-based electronic switch [J].
Organ, MG ;
Arvanitis, EA ;
Dixon, CE ;
Cooper, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1288-1294
[42]  
Orita A, 1999, CHEM-EUR J, V5, P1355, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1355::AID-CHEM1355>3.3.CO
[43]  
2-S
[44]   Rhodium-mediated dipolar cycloaddition of diazoquinolinediones [J].
Pirrung, MC ;
Blume, F .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3642-3649
[45]   EQUILIBRIA AND KINETICS OF HYDROLYSIS OF EBIFURAMIN (NSC-201047), AN AZOMETHINE-CONTAINING STRUCTURE EXHIBITING A REVERSIBLE DEGRADATION STEP IN ACIDIC SOLUTIONS [J].
PRANKERD, RJ ;
STELLA, VJ .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1989, 52 (01) :71-78
[46]   An annulative approach to highly substituted indoles: Unusual effect of phenolic additives on the success of the arylation of ketone enolates [J].
Rutherford, JL ;
Rainka, MP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) :15168-15169
[47]   Quinoline alkaloids: Synthesis of pyrano[2,3-b]quinolines, khaplofoline, lunacrine, and demethoxylunacrine [J].
Sekar, M ;
Prasad, KJR .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (02) :294-296
[48]   A NEW SYNTHESIS OF FURO[2,3-B]PYRIDINE DERIVATIVES (1) [J].
SNYDER, HR ;
EBETINO, FF .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1966, 3 (02) :202-&
[49]   Lewis acid behavior of cationic complexes of palladium(II) and platinum(II): some examples of catalytic applications [J].
Strukul, G .
TOPICS IN CATALYSIS, 2002, 19 (01) :33-42
[50]   Discovery of new multi component reactions with combinatorial methods [J].
Weber, L ;
Illgen, K ;
Almstetter, M .
SYNLETT, 1999, (03) :366-374